- Synthesis, characterization, crystal structures and biological screening of 4-amino quinazoline sulfonamide derivatives
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Three quinazolin-4-ylamino derivatives containing phenylbenzenesulfonamides (7a-7c)were synthesized by reacting (E)-N'-(2-cyanophenyl)-N,N-dimethyl formamidine (6)with different 4-amino-N-(phenyl)benzenesulfonamides (4a-4c)and characterized by different techniques such as HRMS, IR, 1H NMR and 13C NMR spectroscopy. The structural properties were further examined by single crystal X-ray diffraction method. The X-ray data shows that compounds 7a and 7c contain two molecules and 7b contains one molecule in the asymmetric unit. Comparison of conformation of two distinct molecules, “A” and “B”, in the asymmetric unit of 7a and 7c were studied with the aid of reported literature. The in vitro antiproliferative activity of the compounds was tested against two breast cancer cell lines (MDA-MB-231 and MCF7). Compound 7b observed as a highest potent candidate against MDA-MB-231with IC50 of 5.44 μg/mL. Antimicrobial activity was also screened against bacterial and fungal strains. Compound 7a with chloro substitution was observed as the most potent candidate against the Gram-negative bacterial strains, whereas the compounds showed no significant activity against the fungal strain.
- Sunil Kumar,Kudva, Jyothi,Lahtinen, Manu,Peuronen, Anssi,Sadashiva, Rajitha,Naral, Damodara
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- Synthesis and in vitro antimicrobial activity of some newer quinazolinone-sulfonamide linked hybrid heterocyclic entities derived from glycine
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A novel series of 4-(amino or acetamido)-N-{[3-(substituted aryl)-4-oxo-3,4-dihydroquinazolin-2-yl]-methyl}benzenesulfonamide derivatives (1-19) were designed to assimilate 4-quinazolone and sulfonamide moieties in a single molecular framework. To derive entitled hybrid entities with structural diversity, an efficient multi-step synthetic approach initiated from glycine was developed, which involves milder conditions for emphasizing steps viz., reaction in aqueous-media, phosphazo-method of condensation, base mediated selective ester-cleavage, along with key-step, rapid and improved Grimmel's hetero-cyclization method. The structure of the synthesized compounds was confirmed by physico-chemical characteristics and spectroscopic investigations. All these compounds were screened for their in vitro antimicrobial activity. The minimum inhibitory concentrations of the synthesized compounds against various bacteria (S. aureus, B. cereus, E. coli, K. pneumonia, P. aeruginosa) and fungus (A. niger, C. albicans) was measured by broth microdilution assay. Further, results on the preliminary biological activity indicated that most of the screened compounds have displayed varied degree of inhibitory actions.
- Vanparia, Satish F.,Patel, Tarosh S.,Dixit, Ritu B.,Dixit, Bharat C.
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- Design, synthesis and antimicrobial evaluation of novel benzimidazole-incorporated sulfonamide analogues
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A novel series of benzimidazole-incorporated sulfonamide analogues were designed and synthesized with an effort to overcome the increasing antibiotic resistance. Compound 5c gave potent activities against Gram-positive bacteria and fungi, and 2,4-dichlorobenzyl derivative 5g showed good activities against Gram-negative bacteria. Both of these two active molecules 5c and 5g could effectively intercalate into calf thymus DNA to form compound?DNA complex respectively, which might block DNA replication to exert their powerful antimicrobial activity. Molecular docking experiments suggested that compounds 5c and 5g could insert into base-pairs of DNA hexamer duplex by the formation of hydrogen bonds with guanine of DNA. The transportation behavior of these highly active compounds by human serum albumin (HSA) demonstrated that the electrostatic interactions played major roles in the strong association of active compounds with HSA, and which was also confirmed by the full geometry calculation optimizations.
- Zhang, Hui-Zhen,He, Shi-Chao,Peng, Yan-Jun,Zhang, Hai-Juan,Gopala, Lavanya,Tangadanchu, Vijai Kumar Reddy,Gan, Lin-Ling,Zhou, Cheng-He
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- An alternative synthetic process of p-acetaminobenzenesulfonyl chloride through combined chlorosulfonation by HClSO3 and PCl5
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P-Aminobenzene sulfonamide (sulfanilamide, SN) is the simplest and most-used sulfonamide medicine. The key step of SN production via the commonly used chlorosulfonic acid routine is the synthesis of p-acetaminobenzenesulfonyl chloride (P-ASC). A large amount of HSO3Cl has to be used in the traditional process, which results in serious environmental problems. In this study, an alternative chlorosulfonic acid process to synthesize P-ASC was investigated by partially substituting HSO3Cl by PCl5 as the chlorination agent. Compared with the traditional process, the molar ratio of HSO3Cl to acetanilide (the main raw material) can be decreased from 4.96 to 2.1 using CCl4 as the diluent; also, addition of a small amount of NH4Cl was found to significantly increase the P-ASC yield. Operating conditions of the reaction were studied first by single-factor experiments and later by orthogonal experiments to obtain optimum operating conditions under which the P-ASC yield can reach as high as 86.3 %.
- Tan, Shiyu,Yang, Yang,Luo, Ziping,Zhao, Shuo,Huang, Dafu,Zhang, Jun,Dong, Lichun,Wang, Gang
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- A new, mild preparation of sulfonyl chlorides
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A new method was developed for the preparation of sulfonyl chlorides from sulfonic acids under neutral conditions using 2,4,6-trichloro-1,3,5-triazine as chlorinating agent.
- Blotny, Grzegorz
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- Fluorescence sensing and binding behavior of aminobenzenesulfonamidoquinolino-β-cyclodextrin to Zn2+
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(Chemical Equation Presented) A water-soluble fluorescent zinc sensor which binds strongly to Zn2+ (log K = 12.4) was successfully synthesized under physiological conditions. This sensor exhibits a good fluorescence response to Zn2+ over a wide pH range in water. Under the same conditions, several metal ions commonly present in a physiological environment, such as Na+, K+, Ca2+, Mg2+, Mn 2+, Fe2+, and Co2+, showed little interference to the fluorescence response to Zn2+.
- Liu, Yu,Zhang, Ning,Chen, Yong,Wang, Li-Hua
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- Unique para-aminobenzenesulfonyl oxadiazoles as novel structural potential membrane active antibacterial agents towards drug-resistant methicillin resistant Staphylococcus aureus
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A class of structurally unique para-aminobenzenesulfonyl oxadiazoles as new potential antimicrobial agents was designed and synthesized from acetanilide. Some target para-aminobenzenesulfonyl oxadiazoles showed antibacterial potency. Noticeably, hexyl derivative 8b (MIC = 1 μg/mL) was more active than norfloxacin against drug resistant MRSA. Compound 8b was able to disturb the membrane effectively and intercalate into deoxyribonucleic acid (DNA) to form a steady 8b-DNA complex, which might be responsible for bacterial metabolic inactivation. Molecular docking indicated that 8b could interact with DNA topoisomerase IV through noncovalent interactions to form a supramolecular complex and hinder the function of this enzyme. These results indicated that hexyl derivative 8b deserved further investigation as a new lead compound.
- Wang, Juan,Ansari, Mohammad Fawad,Zhou, Cheng-He
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- A facile reaction to access novel structural sulfonyl-hybridized imidazolyl ethanols as potential DNA-targeting antibacterial agents
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A novel type of sulfonyl-hybridized imidazolyl ethanols as potential DNA-targeting antibacterial agents was constructed via the unique ring-opened reaction of oxiranes by imidazoles for the first time. Some developed target hybrids showed potential antimicrobial potency against the tested microbes. Especially, imidazole derivative 5f could strongly suppressed the growth of MRSA (MIC = 4 μg/mL), which was 2-fold and 16-fold more potent than the positive control sulfathiazole and norfloxacin. This compound exhibited quite low propensity to induce bacterial resistance. Antibacterial mechanism exploration indicated that compound 5f could embed in MRSA DNA to form steady 5f-DNA complex, which possibly hinder DNA replication to exert antimicrobial behavior. Molecular docking showed that molecule 5f could bind with dihydrofolate synthetase through hydrogen bonds. These results implied that imidazole derivative 5f could be served as a promising molecule for the exploration of novel antibacterial candidates.
- Bheemanaboina, Rammohan R. Yadav,Guan, Zhi,Hu, Yuan-Yuan,Meng, Jiang-Ping,Wang, Juan,Zhou, Cheng-He
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- Novel Schiff base-bridged multi-component sulfonamide imidazole hybrids as potentially highly selective DNA-targeting membrane active repressors against methicillin-resistant Staphylococcus aureus
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A new type of Schiff base-bridged multi-component sulfonamide imidazole hybrids with antimicrobial potential was developed. Some target compounds showed significant antibacterial potency. Observably, butylene hybrids 4h exhibited remarkable inhibitory efficacy against clinical MRSA (MIC = 1 μg/mL), but had no significant toxic effect on normal mammalian cells (RAW 264.7). The highly active molecule 4h was revealed by molecular modeling study that it could insert into the base-pairs of DNA hexamer duplex and bind with the ASN-62 residue of human carbonic anhydrase isozyme II through hydrogen bonding. Furthermore, further preliminary antibacterial mechanism experiments confirmed that compound 4h could effectively interfere with MRSA membrane and insert into bacterial DNA isolated from clinical MRSA strains through non-covalent bonding to produce a supramolecular complex, thus exerting its strong antibacterial efficacy by impeding DNA replication. These findings strongly implied that the highly active hybrid 4h could be used as a potential DNA-targeting template for the development of valuable antimicrobial agent.
- Hu, Yuanyuan,Pan, Guangxing,Yang, Zhixiong,Li, Tiejun,Wang, Juan,Ansari, Mohammad Fawad,Hu, Chunfang,Yadav Bheemanaboina, Rammohan R.,Cheng, Yu,Zhou, Chenghe,Zhang, Jiaheng
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- Novel 2,3-disubstituted quinazoline-4(3H)-one molecules derived from amino acid linked sulphonamide as a potent malarial antifolates for DHFR inhibition
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An optimization of a modified Grimmel's method for N-heterocyclization of Leucine linked sulphonamide leading to 2,3-disustituted-4-quinazolin-(3H)-ones was accomplished. Further, nineteen hybrid quinazolinone motifs (5a-5s) were synthesized by N-heterocyclization reaction under microwave irradiation using TEAA (IL) as green solvent as well as catalyst. The in vitro screening of the hybrid entities against the plasmodium species P. falciparum yielded five antimalarial potent molecules 5g, 5l, 5m, 5n & 5p owing comparable activity to the reference drugs. The active scaffolds were further evaluated for enzyme inhibition efficacy against alleged receptor Pf-DHFR computationally as well as in vitro, proving their candidature as lead dihydrofolate reductase inhibitors. The prediction of the ADMET properties of the potent molecules also indicated their good oral bioavailability.
- Patel, Tarosh S.,Vanparia, Satish F.,Patel, Urmila H.,Dixit, Ritu B.,Chudasama, Chaitanya J.,Patel, Bhavesh D.,Dixit, Bharat C.
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- Ionic liquid mediated stereoselective synthesis of alanine linked hybrid quinazoline-4(3H)-one derivatives perturbing the malarial reductase activity in folate pathway
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Grimmel's method was optimized as well as modified leading to the cyclization and incorporation of alanine linked sulphonamide in 4-quinazolin-(3H)-ones. Further, the generation of heterocyclic motif at position-3 of 4-quinazolinones was explored by synthesis of imines, which unfortunately led to an isomeric mixture of stereoisomers. The hurdle of diastereomers encountered on the path was eminently rectified by development of new rapid and reproducible methodology involving the use of imidazolium based ionic liquid as solvents as well as catalyst for cyclization as well as synthesis of imines in situ at position-3 leading to procurement of single E-isomer as the target hybrid heterocyclic molecules. The purity and presence of single isomer was also confirmed by HPLC and spectroscopic techniques. Further, the synthesized sulphonamide linked 4-quinazolin-(3H)-ones hybrids were screened for their antimalarial potency rendering potent entities (4b, 4c, 4 l, 4 t and 4u). The active hybrids were progressively screened for enzyme inhibitory efficacy against presumed receptor Pf-DHFR and h-DHFR computationally as well as in vitro, proving their potency as dihydrofolate reductase inhibitors. The ADME properties of these active molecules were also predicted to enhance the knowhow of the oral bioavailability, indicating good bioavailability of the active entities.
- Patel, Tarosh S.,Bhatt, Jaimin D.,Vanparia, Satish F.,Patel, Urmila H.,Dixit, Ritu B.,Chudasama, Chaitanya J.,Patel, Bhavesh D.,Dixit, Bharat C.
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- Green synthesis, biological evaluation, molecular docking studies and 3D-QSAR analysis of novel phenylalanine linked quinazoline-4(3H)-one-sulphonamide hybrid entities distorting the malarial reductase activity in folate pathway
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A modified Grimmel's method for N-heterocyclization of phenylalanine linked sulphonamide side arm at position-2 was optimized leading to 2,3-disustituted-4-quinazolin-(3H)-ones. Further, [Bmim][BF4]-H2O (IL) was used as green solvent as well as catalyst for the synthesis of twenty two hybrid quinazolinone motifs (4a-4v) by N-heterocyclization reaction using microwave irradiation technique. The in vitro screening of the hybrid entities against the malarial species Plasmodium falciparum yielded five potent molecules 4l, 4n, 4r, 4t & 4u owing comparable antimalarial activity to the reference drugs. In continuation, an in silico study was carried out to obtain a pharmacophoric model and quantitative structure activity relationship. We also built a 3D-QSAR model to procure more information that could be applied to design new molecules with more potent Pf-DHFR inhibitory activity. The designed pharmacophore was recognized to be more potent for the selected molecules, exhibiting five pharmacophoric features. The active scaffolds were further evaluated for enzyme inhibition efficacy against alleged receptor Pf-DHFR computationally and in vitro, proving their candidature as lead dihydrofolate reductase inhibitors as well as the selectivity of the test candidates was ascertained by toxicity study against vero cells. The perception of good oral bioavailability was also proved by study of pharmacokinetic properties.
- Patel, Tarosh S.,Bhatt, Jaimin D.,Dixit, Ritu B.,Chudasama, Chaitanya J.,Patel, Bhavesh D.,Dixit, Bharat C.
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- Design, solvent-free synthesis and antibacterial activity evaluation of new coumarin sulfonamides
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A simple cost-effective and green method was presented for the synthesis of coumarin bis sulfonamides. Seventeen novel coumarin sulfonamides were synthesized in good to high yield and purity in six steps starting from 2-amino thiazole, aniline, and 4-methoxy aniline. All of the reactions have been done under green conditions without using any hazardous solvent. The chemical structures of the products were elucidated by IR, 1H NMR, and 13C NMR spectroscopy and elemental analysis. Also, the anti-bacterial properties of the synthesized sulfonamides were investigated using two strains of Staphylococcus (gram-positive) and Escherichia coli (gram-negative) bacteria.
- Aminarshad, Farzaneh,Heidari, Shima,Mostajeran, Neda,Massah, Ahmad Reza
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p. 547 - 562
(2021/08/16)
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- Preparation method of P-acetyl aminobenzene sulfonyl chloride
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The invention provides a preparation method of p-acetyl aminobenzene sulfonyl chloride. The method uses acetanilide and chlorosulfonic acid as raw materials to prepare p-acetyl aminobenzenesulfonic acid by sulfonation reaction in the presence of a catalyst. The method is simple in process, free of special requirements for equipment, simple and convenient to operate, less in three wastes, good in product quality and suitable for industrial production.
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Paragraph 0033-0046
(2021/11/14)
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- Beyond Basicity: Discovery of Nonbasic DENV-2 Protease Inhibitors with Potent Activity in Cell Culture
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The viral serine protease NS2B-NS3 is one of the promising targets for drug discovery against dengue virus and other flaviviruses. The molecular recognition preferences of the protease favor basic, positively charged moieties as substrates and inhibitors, which leads to pharmacokinetic liabilities and off-target interactions with host proteases such as thrombin. We here present the results of efforts that were aimed specifically at the discovery and development of noncharged, small-molecular inhibitors of the flaviviral proteases. A key factor in the discovery of these compounds was a cellular reporter gene assay for the dengue protease, the DENV2proHeLa system. Extensive structure-activity relationship explorations resulted in novel benzamide derivatives with submicromolar activities in viral replication assays (EC50 0.24 μM), selectivity against off-target proteases, and negligible cytotoxicity. This structural class has increased drug-likeness compared to most of the previously published active-site-directed flaviviral protease inhibitors and includes promising candidates for further preclinical development.
- Kühl, Nikos,Leuthold, Mila M.,Behnam, Mira A. M.,Klein, Christian D.
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supporting information
p. 4567 - 4587
(2021/05/06)
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- Comparative study between the anti-P. falciparum activity of triazolopyrimidine, pyrazolopyrimidine and quinoline derivatives and the identification of new PfDHODH inhibitors
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In this work, we designed and synthesized 35 new triazolopyrimidine, pyrazolopyrimidine and quinoline derivatives as P. falciparum inhibitors (3D7 strain). Thirty compounds exhibited anti-P. falciparum activity, with IC50 values ranging from 0.030 to 9.1 μM. The [1,2,4]triazolo[1,5-a]pyrimidine derivatives were more potent than the pyrazolo[1,5-a]pyrimidine and quinoline analogues. Compounds 20, 21, 23 and 24 were the most potent inhibitors, with IC50 values in the range of 0.030–0.086 μM and were equipotent to chloroquine. In addition, the compounds were selective, showing no cytotoxic activity against the human hepatoma cell line HepG2. All [1,2,4]triazolo[1,5-a]pyrimidine derivatives inhibited PfDHODH activity in the low micromolar to low nanomolar range (IC50 values of 0.08–1.3 μM) and did not show significant inhibition against the HsDHODH homologue (0–30% at 50 μM). Molecular docking studies indicated the binding mode of [1,2,4]triazolo[1,5-a]pyrimidine derivatives to PfDHODH, and the highest interaction affinities for the PfDHODH enzyme were in agreement with the in vitro experimental evaluation. Thus, the most active compounds against P. falciparum parasites 20 (R = CF3, R1 = F; IC50 = 0.086 μM), 21 (R = CF3; R1 = CH3; IC50 = 0.032 μM), 23, (R = CF3, R1 = CF3; IC50 = 0.030 μM) and 24 (R = CF3, 2-naphthyl; IC50 = 0.050 μM) and the most active inhibitor against PfDHODH 19 (R = CF3, R1 = Cl; IC50 = 0.08 μM - PfDHODH) stood out as new lead compounds for antimalarial drug discovery. Their potent in vitro activity against P. falciparum and the selective inhibition of the PfDHODH enzyme strongly suggest that this is the mechanism of action underlying this series of new [1,2,4]triazolo[1,5-a]pyrimidine derivatives.
- Silveira, Flávia F.,de Souza, Juliana O.,Hoelz, Lucas V.B.,Campos, Vinícius R.,Jabor, Valquíria A.P.,Aguiar, Anna C.C.,Nonato, M. Cristina,Albuquerque, Magaly G.,Guido, Rafael V.C.,Boechat, Nubia,Pinheiro, Luiz C.S.
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- Design, synthesis and biological evaluation of novel naphthoquinone-4-aminobenzensulfonamide/carboxamide derivatives as proteasome inhibitors
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A series of novel 4-aminobenzensulfonamide/carboxamide derivatives bearing naphthoquinone pharmacophore were designed, sythesized and evaluated for their proteasome inhibitory and antiproliferative activities against human breast cancer cell line (MCF-7). The structures of the synthesized compounds were confirmed by spectral and elemental analyses. The proteasome inhibitory activity studies were carried out using cell-based assay. The antiproteasomal activity results revealed that most of the compounds exhibited inhibitory activity with different percentages against the caspase-like (C-L, β1 subunit), trypsin-like (T-L, β2 subunit) and chymotrypsin-like (ChT-L, β5 subunit) activities of proteasome. Among the tested compounds, compound 14 bearing 5-chloro-2-pyridyl ring on the nitrogen atom of sulfonamide group is the most active compound in the series and displayed higher inhibition with IC50 values of 9.90 ± 0.61, 44.83 ± 4.23 and 22.27 ± 0.15 μM against ChT-L, C-L and T-L activities of proteasome compared to the lead compound PI-083 (IC50 = 12.47 ± 0.21, 53.12 ± 2.56 and 26.37 ± 0.5 μM), respectively. The antiproliferative activity was also determined by MTT (3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide) assay in vitro. According to the antiproliferative activity results, all of the compounds exhibited cell growth inhibitory activity in a range of IC50 = 1.72 ± 0.14–20.8 ± 0.5 μM and compounds 13 and 28 were found to be the most active compounds with IC50 values of 1.79 ± 0.21 and 1.72 ± 0.14 μM, respectively. Furthermore, molecular modeling studies were carried out for the compounds 13, 14 and 28 to investigate the ligand-enzyme binding interactions.
- Uysal, Sirin,Soyer, Zeynep,Saylam, Merve,Tarikogullari, Ayse H.,Yilmaz, Sinem,Kirmizibayrak, Petek Ballar
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- Quinoline carboxamide core moiety-based compounds inhibit P. falciparum falcipain-2: Design, synthesis and antimalarial efficacy studies
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Targeting Falcipain-2 (FP2) for the development of antimalarials is a promising and established concept in antimalarial drug discovery and development. FP2, a member of papain-family cysteine protease of the malaria parasite Plasmodium falciparum holds an important role in hemoglobin degradation pathway. A new series of quinoline carboxamide-based compounds was designed, synthesized and evaluated for antimalarial activity. We integrated molecular hybridization strategy with in-silico drug design to develop FP2 inhibitors. In-vitro results of FP2 inhibition by Qs17, Qs18, Qs20 and Qs21 were found to be in low micromolar range with IC50 4.78, 7.37, 2.14 and 2.64 μM, respectively. Among the 25 synthesized compounds, four compounds showed significant antimalarial activities. These compounds also depicted morphological and food-vacuole abnormalities much better than that of E-64, an established FP2 inhibitor. Overall these aromatic substituted quinoline carboxamides can serve as promising leads for the development of novel antimalarial agents.
- Singh, Anju,Kalamuddin, Md,Maqbool, Mudasir,Mohmmed, Asif,Malhotra, Pawan,Hoda, Nasimul
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- Discovery of new phenyl sulfonyl-pyrimidine carboxylate derivatives as the potential multi-target drugs with effective anti-Alzheimer's action: Design, synthesis, crystal structure and in-vitro biological evaluation
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Alzheimer's disease (AD) is multifactorial, progressive neurodegeneration with impaired behavioural and cognitive functions. The multitarget-directed ligand (MTDL) strategies are promising paradigm in drug development, potentially leading to new possible therapy options for complex AD. Herein, a series of novel MTDLs phenylsulfonyl-pyrimidine carboxylate (BS-1 to BS-24) derivatives were designed and synthesized for AD treatment. All the synthesized compounds were validated by 1HNMR, 13CNMR, HRMS, and BS-19 were structurally validated by X-Ray single diffraction analysis. To evaluate the plausible binding affinity of designed compounds, molecular docking study was performed, and the result revealed their significant interaction with active sites of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The synthesized compounds displayed moderate to excellent in vitro enzyme inhibitory activity against AChE and BuChE at nanomolar (nM) concentration. Among 24 compounds (BS-1 to BS-24), the optimal compounds (BS-10 and BS-22) displayed potential inhibition against AChE; IC50 = 47.33 ± 0.02 nM and 51.36 ± 0.04 nM and moderate inhibition against BuChE; IC50 = 159.43 ± 0.72 nM and 153.3 ± 0.74 nM respectively. In the enzyme kinetics study, the compound BS-10 displayed non-competitive inhibition of AChE with Ki = 8 nM. Respective compounds BS-10 and BS-22 inhibited AChE-induced Aβ1-42 aggregation in thioflavin T-assay at 10 μM and 20 μM, but BS-10 at 10 μM and 20 μM concentrations are found more potent than BS-22. In addition, the aggregation properties were determined by the dynamic light scattering (DLS) and was found that BS-10 and BS-22 could significantly inhibit self-induced as well as AChE-induced Aβ1-42 aggregation. The effect of compounds (BS-10 and BS-22) on the viability of MC65 neuroblastoma cells and their capability to cross the blood-brain barrier (BBB) in PAMPA-BBB were further studied. Further, in silico approach was applied to analyze physicochemical and pharmacokinetics properties of the designed compounds via the SwissADME and PreADMET server. Hence, the novel phenylsulfonyl-pyrimidine carboxylate derivatives can act as promising leads in the development of AChE inhibitors and Aβ disaggregator for the treatment of AD.
- Manzoor, Shoaib,Prajapati, Santosh Kumar,Majumdar, Shreyasi,Raza, Kausar,Gabr, Moustafa T.,Kumar, Shivani,Pal, Kavita,Rashid, Haroon,Kumar, Suresh,Krishnamurthy, Sairam,Hoda, Nasimul
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- Method for producing p-acetamidobenzenesulfonyl chloride based on double-temperature-zone two-stage method of continuous flow reaction
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The invention relates to a method for producing p-acetamidobenzenesulfonyl chloride by a double-temperature-zone two-stage method based on a continuous flow reaction. The method comprises the following steps: reacting acetanilide with chlorosulfonic acid to generate p-acetamidobenzenesulfonic acid, and reacting p-acetamidobenzenesulfonic acid with chlorosulfonic acid to generate p-acetamidobenzenesulfonyl chloride. The characteristics of efficient mass transfer and heat transfer, controllable reaction time and reaction temperature, continuous production, intrinsic safety and the like of a micro-channel reactor are utilized, a double-temperature-zone micro-channel reactor is used, and a first reaction section adopts a lower temperature, so that generation of a para-sulfonation product is facilitated, and in the second reaction stage, high temperature is adopted, so that sulfonyl chloride is generated. The method solves the problems of low temperature, slow reaction and generation of by-products due to high temperature, safety accidents caused by release of a large amount of reaction heat in the production process are avoided, the stable production is ensured by controlling the reaction time and the reaction temperature, and pollution caused by excessive chlorosulfonic acid used in the batch production process is reduced.
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Page/Page column 5-7
(2020/05/02)
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- Design and synthesis of novel sulfonamide-derived triazoles and bioactivity exploration
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Objective: Due to the incidence of resistance, a series of sulfonamide-derived 1,2,4-triazoles were synthesized and evaluated. Method: The novel sulfonamide-derived 1,2,4-triazoles were prepared starting from commercial acetaniline and chlorosulfonic acid by sulfonylation, aminolysis, N-alkylation and so on. The antimicrobial activity of the synthesized compounds were evaluated in vitro by two-fold serial dilution technique. Results: In vitro antimicrobial evaluation found that 2-chlorobenzyl sulfonamide 1,2,4-triazole 7c exhibited excellent antibacterial activities against MRSA, B. subtilis, B. typhi and E. coli with MIC values of 0.02?0.16 μmol/mL, which were comparable or even better than Chloromycin. The preliminary mechanism suggested that compound 7c could effectively bind with DNA, and also it could bind with human microsomal heme through hydrogen bonds in molecular docking. Computational chemical studies were performed on compound 7c to understand the structural features that are essential for activity. Additionally, compound 7c could generate a small amount of reactive oxygen species (ROS). Conclusion: Compound 7c could serve as a potential clinical antimicrobial candidate.
- He, Shi-Chao,Sun, Qing,Zhang, Hai-Juan,Zhang, Hui-Zhen,Zhou, Cheng-He
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p. 104 - 118
(2020/02/04)
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- Synthesis, antimicrobial, and docking investigations of remarkably modified sulfathiazole derivatives
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SOME new sulfathiazole derivatives were synthesized. The sulfathiazole starting material was reacted with ethyl bromoacetate and gave unpredictably an ester product 2. The substitution occurred selectively at the tautomeric proton of the NH thiazolyl nitrogen rather than the aromatic NH2 protons. The ester was further hydrazinolysed followed by condensation with several aldehydes to establish hydrazones (4a-h). Hantzesch thiazole synthesis was also applied to build antimicrobial agents containing multi-thiazole moieties. The structures of the synthesized compounds were confirmed by 1H, 13C, 2D 1H NMR, MS, and microanalyses. The synthesized compounds were tested for their antimicrobial activity towards Gram-positive and Gram-negative bacteria, and fungi strains. Some of the investigated compounds showed prominent high potency. The docking study revealed the mode of action between the modified sulfathiazole ligands and the binding site of DHPS.
- Gaballah, Samir T.,Amer,Hofinger-Horvath,Al-Moghazy,Hemida
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p. 171 - 184
(2020/04/09)
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- Method for synthesizing p-acetamidobenzene sulfonyl chloride in tetrachloroethylene solvent
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The invention relates to a method for synthesizing p-acetamidobenzene sulfonyl chloride in a tetrachloroethylene solvent. The method comprises the following steps: mixing tetrachloroethylene with chlorosulfonic acid in a reactor, and adding acetanilide, wherein the temperature during the process of adding acetanilide is controlled at 10-12 DEG C; after the acetanilide is added, heating the mixtureto a temperature of 45-55 DEG C, and carrying out chlorosulfonation for 80-90 minutes; continuing to carrying out heating, adding thionyl chloride when the temperature is 60-70 DEG C, and carrying out reaction at 60-70 DEG C for 80-90 minutes; evaporating 50%-70% of the tetrachloroethylene solvent under a reduced pressure state; continuing to carry out the reaction at 60-70 DEG C for 50-65 minutes; and stopping the reaction, carrying out cooling and standing, carrying out dilution segregation by virtue of an ice-water mixture, and carrying out suction filtration and baking. By implementing the technique of the invention, the use amount of the chlorosulfonic acid can be obviously reduced, and the yield of ASC is increased from 90% or less to 98% or more. The output of waste acid is obviously reduced, and the cost for environmental protection treatment is relatively low.
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Paragraph 0031-0051
(2019/12/31)
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- Sulfonamide-Derived Four-Component Molecular Hybrids as Novel DNA-Targeting Membrane Active Potentiators against Clinical Escherichia coli
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Novel sulfonamide-based four-component molecular hybrids as potential DNA-targeting antimicrobial agents were developed from marketed acetanilide through convenient procedures. Biological assays indicated that a few of the target compounds showed significant inhibitory efficiencies toward the tested bacteria and fungi. Noticeably, metronidazole hybrid 6a exhibited a lower minimum inhibitory concentration (MIC) value of 0.019 mM against clinical drug-resistant Escherichia coli (E. coli), which showed to be 84-fold more active than clinical norfloxacin and had no obvious toxicity toward human breast cancer MCF-7 cells. Synergistic combinations of compound 6a with clinical antibacterial or antifungal drugs could improve the antimicrobial efficiency. Further molecular modeling indicated that the active molecule 6a could bind with THR-199, HIS-64, and GLN-92 residues of human carbonic anhydrase isozyme II through hydrogen bonds and was also able to insert into base-pairs of the DNA hexamer duplex by forming hydrogen bonds. The preliminary exploration of the antibacterial mechanism suggested that compound 6a was capable of disturbing the E. coli membrane effectively and intercalating into clinical resistant E. coli bacterial DNA through noncovalent bonds to form a supramolecular complex, thus exerting its powerful antimicrobial activity. This might suggest a great possibility for hybrid 6a to be a DNA-targeting membrane active potentiator against clinical drug-resistant E. coli.
- Hu, Yuan-Yuan,Yadav Bheemanaboina, Rammohan R.,Battini, Narsaiah,Zhou, Cheng-He
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p. 1036 - 1052
(2019/02/14)
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- Para-ester synthesis and wastewater treatment method
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The invention relates to the technical field of para-ester synthesis, and discloses a para-ester synthesis and wastewater treatment method. Through the separation of the lowtemperature sulfonation process from the high-temperature sulfonation process, the content of a byproduct produced in the reaction process can be minimized; through the addition of copper sulfate powder during a sulfonation reaction, the reaction speed can be increased; along with the progresses of the sulfonation reaction, produced water gradually dilutes concentrated sulfuric acid, so that the reaction becomes slower andslower; however, the copper sulfate powder cannot automatically absorb moisture, is separated out from a diluted solution, has five crystal water molecules and becomes copper sulfate pentahydrate, anda copper sulfate solution is acidic, so that the reaction speed is increased to a certain extent; through the addition of the suction filtration process after a main composition in each step, in theprocess of carrying out the para-ester synthesis and wastewater treatment method, the precipitation purification can be performed on a product in each step, so that the purity of the finally obtainedpara-ester is increased.
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Paragraph 0029; 0033-0034; 0045; 0049-0050; 0061; 0065-0066
(2019/07/04)
-
- USP30 INHIBITORS
-
The application relates to phenyl- or naphthylsulfonamide derivatives of the structural formula (I). The compounds are described as inhibitors of USP30 (ubiquitin specific peptidase 30) useful for the treatment of conditions involving mitochondrial defects including neurodegenerative diseases such as Alzheimer's and Parkinson's or a neoplastic disease such as leukemia.
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Page/Page column 38
(2018/12/13)
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- Has high water washing fastness and bears the friction fastness reactive red dye and the preparation method
-
The invention discloses a reactive red dye with high washing fastness and rubbing fastness and a preparation method of the reactive red dye. Acetanilide reacts with chlorosulfonic acid and sulfoxide chloride to generate acetylsulfanilyl chloride; acetylsulfanilyl chloride is condensed with a sulfide generate by reacting a 2-chlorethamin hydrochloride with mercaptoethanol to obtain thioether; the thioether is oxidized and esterified to obtain 2-[2-(4-aminobenzenesulfonamido) ethyl sulfuryl] hydroxyethyl sulfate which is primarily condensed with cyanuric chloride and secondarily condensed with H acid to obtain a condensation compound; the condensation compound is cooled and then coupled with the diazonium salt of 1.5 acid under an alkaline condition, and the product is filtered and then the filtrate is collected and is subjected to direct spray drying to obtain a semi-finished product. The reactive red dye has the characteristics of bright color, high solubility high substantivity, high compatibility, high lifting power, high fixation rate, excellent diversified fastness and the like. The reactive red dye is suitable for dyeing, printing and pad dyeing of cellulosic fibers, protein fibers, viscose and polyarmide fibers, and higher than common types in rubbing fastness and washing fastness by 0.5 to 1 level.
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Paragraph 0046-0048; 0065
(2018/03/01)
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- Active benzene sulfonamide ethyl sulphone base hydroxy ethyl sulfate aniline compounds of preparation method (by machine translation)
-
The invention discloses a benzene sulfonamide ethyl sulphone base hydroxy ethyl sulfate aniline compound and its preparation method, acetyl aniline with chlorosulfuric acid, thionyl chloride reaction generating P-acetyl amino sulfonyl chloride, with 2 - chloroethylamine hydrochloride and mercapto ethanol produced by the reaction of sulfide condensation shall thioether, the thioether re-oxidation, esterification or sulfonated to obtain 2 - [2 - (4 - amino sulfuryl amidogen) sulfuryl] hydroxy ethyl sulfate or 2 - [2 - (4 - amino sulfuryl amidogen) sulfuryl] hydroxy ethyl sulfate - 3 - sulfonic acid. The active benzene sulfonamide ethyl sulphone base hydroxy ethyl sulfate aniline compound with 4 - (2 - hydroxyethyl sulphone sulfate) compared with the aniline; synthesis of the reactive dye has a bright, low substantivity, uptake, fixation is relatively high, the hydrolysis of the dye is little, and the like excellent fastness, especially light fastness, high color fastness resistance, friction-resistant fastness is higher than the common varieties of 0.5 - 1 level. (by machine translation)
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Paragraph 0044; 0045; 0046
(2018/05/16)
-
- Preparation method of para-ester
-
The invention provides a preparation method of para-ester. The preparation method of para-ester comprises the following steps: under the existence of phosphorus pentoxide, carrying out chlorosulfonation on N-phenylacetamide and chlorosulfonic acid as well as thionyl chloride, thus obtaining a chlorosulfonation composition; and sequentially carrying out reduction reaction, condensation reaction andesterification reaction on the chlorosulfonation composition, thus obtaining para-ester. Compared with the prior art, the preparation method has the advantages that phosphorus pentoxide is added in chlorosulfonation, a balance state is broken, the balance moves to the direction in which 4-acetamidobenzenesulfonyl azide is generated, the conversion rate of N-phenylacetamide is increased, namely the yield of chlorosulfonation is increased, and meanwhile, excessive chlorosulfonic acid is avoided, so that wastewater pollution is alleviated.
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-
Paragraph 0068; 0069
(2018/04/01)
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- A novel reactive blue dye and its preparation method
-
The invention discloses a novel reactive blue dye and a preparation method of the novel reactive blue dye. The preparation method of the compound comprises the following steps: performing condensation on cyanuric chloride and 2-[2-(4-aminobenzenesul fonamide) ethyl sulfuryl] ethoxyl-sulphating compound and then performing secondary condensation on an obtained condensation compound and 2,4-diaminobenzenesulfonic acid; reducing the temperature of the condensate and performing diazotization; performing acid coupling on the condensate and H acid; then performing alkali coupling on the condensate and diazonium salt of sodium sulfamate or 2,5-disulfonic acid-phenylamine; spraying and drying to obtain a semi-finished product. The reactive blue dye has the characteristics of bright and deep color, high dissoluvability, high compatibility, high elevating power, high fixation rate, high firmness degree of all items and the like; the dye is suitable for coloring, printing and pad-dyeing of cellulosic fibers, protein fibers, viscose fibers and polyamide, and the color fasteness to sunlight and the fastness to rubbing of the novel reactive blue dye are 0.5-1 grade more than those of the general varieties.
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-
Paragraph 0016-0017; 0047-0049
(2018/01/11)
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- A new kind of very deep reactive orange or yellow dye and its preparation method
-
The invention discloses a novel ultradeep reactive orange or yellow dye and a preparation method thereof. The preparation method comprises the following steps: carrying out tertiary coupling on 3,5-diamido-benzoic acid and 4-methyl-2-sulfo-aniline (or derivatives), 2-[2-(4-aminophenylsulfamido)ethylsulfuryl]hydroxyethyl sulfate, 2-[2-(4-aminophenylformamido)ethylsulfuryl]hydroxyethyl sulfate or diazonium salt of 2-methoxy- or 2-methyl- or 2-chloro- or 2-hydro- or 2-sulfo-4-(beta-hydroxyethylsulfurylsulfate)aniline, filtering, collecting the filtrate, and directly carrying out spray drying to obtain the semifinished product. The novel ultradeep reactive orange or yellow dye has the characteristics of bright color, deep color, high solubility, especially high compatibility with black, high lifting power, high fixation rate, favorable fastness and the like. The novel ultradeep reactive orange or yellow dye is suitable for dyeing, printing and pad dyeing of cellulose fibers, protein fibers, viscose fibers and polyamide fibers, has higher fastness to rubbing than common varieties by Grade 0.5-1, and has low nylon staining strength.
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Paragraph 0042; 0043; 0044; 0077; 0078; 0079
(2018/01/11)
-
- Synthetic method of p-aminobenzenesulfonamide
-
The invention relates to a synthetic method of p-aminobenzenesulfonamide, which is characterized by successively includes the following steps: (a) adding chlorosulfonic acid into a reaction kettle, controlling the temperature to be 40-50 DEG C, adding acetanilide, increasing the temperature to 55-60 DEG C and performing a reaction for 1-2 h to obtain a first mixture; (b) adding dichloroethane, increasing the temperature to 65-75 DEG C, dropwisely adding a catalyst and SOCl2, and continuously performing the reaction for 1-3 h; (c) controlling the temperature in the reaction kettle to be 15-20 DEG C, dropwisely adding the mixed liquid obtained in the step (b) into ammonia water being 22-25% in mass concentration, stirring the liquid for 0.5-1 h, increasing the temperature to 40-42 DEG C and continuously performing the reaction with stirring for 1-2 h, and filtering the liquid to obtain a crude product of the p-aminobenzenesulfonamide; and (d) adding the crude product in a hydrolysis kettle, adding a NaOH solution being 20-30% in mass concentration, heating the mixture to 90-95 DEG C to perform reflux hydrolysis for 2-3 h, adding an acid solution to regulate the pH value to 6.5-6.7, performing centrifugation, and drying a filter residue to obtain the p-aminobenzenesulfonamide. In the method, the addition quantities of the reactants are accurately controlled so that the use amount of the chlorosulfonic acid is reduced. The method is reduced in cost and is increased in yield and purity of the product.
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-
Paragraph 0007
(2016/10/17)
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- Catalyzed preparation method of sulfamethoxazole
-
The invention provides a catalyzed preparation method of sulfamethoxazole. The preparation method comprises the following steps: synthesis of p-acetamidobenzene sulfonyl chloride, synthesis of 3-(p-acetamidobenzene sulfonamide)-5-methylisoxazole, and synthesis of sulfamethoxazole; and the method has a high yield, and accords with needs of industrial large-scale production.
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-
Paragraph 0013; 0015; 0020; 0025; 0030; 0035
(2018/02/04)
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- A direct synthesis by solvent extraction the chlorine does the method of P-acetyl amino sulfonyl
-
The invention discloses a method for direct synthesis of a p-acetamidobenzene sulfonyl chloride dried product by solvent extraction. The method is characterized in that in sulfonation, chloroform is used; after a reaction is finished, cooling and layering processes are carried out; the upper solvent layer is returned and used for the next sulfonation reaction, the lower product layer is added with dichloroethane and water, and the mixture undergoes an extraction reaction; and through layering, condensation, crystallization and drying, the p-acetamidobenzene sulfonyl chloride dried product is obtained. The method does not produce a wet product, realizes direct synthesis of the p-acetamidobenzene sulfonyl chloride dried product, improves product quality, maximumly reduces chlorosulfonic acid consumption in production, reduces production and a concentration of acid water, and reduces a production cost.
- -
-
Paragraph 0024-0028
(2017/02/09)
-
- Synthesis, Characterization, Thermal and Antimicrobial studies of N-substituted Sulfanilamide derivatives
-
Four sulfanilamide derivatives N-[4-(phenylsulfamoyl)phenyl]acetamide (1), 4-amino-N-phenylbenzenesulfonamide (2), N-[4-(phenylsulfamoyl)phenyl]benzamide (3) and N-{4-[(3-chlorophenyl)sulfamoyl]phenylbenzamide (4) were synthesized and characterized by Infra-Red (IR), Nuclear Magnetic Resonance (NMR) and UV-visible (UV-Vis) spectra. Also Liquid Chromatographic (LCMS) and High Resolution Mass Spectrometric (HRMS) methods were used. Crystal structures of 1-4 were determined by single crystal X-ray diffraction (XRD) and their conformational and hydrogen bond (HB) network properties were examined with survey of the literature data. Compounds 1 and 2 crystallize in the same orthorhombic Pbca symmetry with equivalent molecular conformation (tilted V-shape) but showed distinct packing and hydrogen bonding models. Compounds 3 and 4 crystallize in monoclinic and triclinic crystal systems, albeit exhibiting identical molecular conformation (L-shaped). Same donor acceptor pairs both on 3 and 4 result to different kind of HB network. Thermogravimetric (TG) and differential scanning calorimetric (DSC) methods were used to evaluate thermal properties of the substances. All sulfanilamide derivatives have melting points between195-227 C, initiation of thermal decomposition between 259-271 C and enthalpies of fusion ΔHfusT = 38.96, 36.60, 46.23 and 44.81 kJ mol -1 were determined for 1-4, respectively. The derivatives were screened for their antibacterial and antifungal activities against various bacterial and fungal strains. It is observed that there is no significant antibacterial activity with the introduction of the benzene ring to CO-NH group or SO2-NH moiety, and none of the compounds exhibited antifungal activity.
- Lahtinen, Manu,Kudva, Jyothi,Hegde, Poornima,Bhat, Krishna,Kolehmainen, Erkki,Nonappa,Venkatesh,Naral, Damodara
-
p. 280 - 290
(2014/02/14)
-
- Novel 2-chloro-4-anilino-quinazoline derivatives as EGFR and VEGFR-2 dual inhibitors
-
Novel 2-chloro-4-anilino-quinazolines designed as EGFR and VEGFR-2 dual inhibitors were synthesized and evaluated for inhibitory effects. EGFR and VEGFR-2 are validated targets in cancer therapy and combined inhibition might be synergistic for both antitumor activity and resistance prevention. The biological data obtained proved the potential of 2-chloro-4-anilino-quinazoline derivatives as EGFR and VEGFR-2 dual inhibitors, highlighting compound 8o, which was approximately 7-fold more potent on VEGFR-2 and approximately 11-fold more potent on EGFR compared to the prototype 7. SAR and docking studies allowed the identification of pharmacophoric groups for both kinases and demonstrated the importance of a hydrogen bond donor at the para position of the aniline moiety for interaction with conserved Glu and Asp amino acids in EGFR and VEGFR-2 binding sites.
- Barbosa, Maria Letícia De Castro,Lima, Lídia Moreira,Tesch, Roberta,Sant'Anna, Carlos Mauricio R.,Totzke, Frank,Kubbutat, Michael H.G.,Sch?chtele, Christoph,Laufer, Stefan A.,Barreiro, Eliezer J.
-
-
- Synthesis and pharmacological evaluation of novel phenyl sulfonamide derivatives designed as modulators of pulmonary inflammatory response
-
In this paper we report the design, synthesis and pharmacological evaluation of a new series of phenyl sulfonamide derivatives 2a-h and 3-8 planned by structural modification on the anti-inflammatory prototype LASSBio-468 (1). Among the synthesized analogues, the tetrafluorophthalimide LASSBio-1439 (2e) stands out showing an in vitro anti-TNF-a effect similar to the standard thalidomide. The relevance of tetrafluorination of the phthalimide nucleus was also confirmed by the anti-inflammatory profile of 2e, through oral administration, in a murine model of pulmonary inflammation. The corresponding tetrafluorocarboxyamide metabolite LASSBio-1454 (15), generated from partial hydrolysis of the derivative 2e, presented a significant in vitro effect and a pronounced anti-inflammatory activity in vivo.
- De Castro Barbosa, Maria Leticia,Ramos, Thiago Jose Figueira,De Arantes, Ana Carolina Santos,Martins, Marco Aurelio,Silva, Patricia Machado Rodriguese,Barreiro, Eliezer J.,Lima, Lidia Moreira
-
p. 14651 - 14672
(2013/02/26)
-
- Possible antineoplastic agents, part XVII: Synthesis, antitumor and antiangiogenic study of few bioisosteres of thalidomide metabolites
-
Two series of bioisostere of thalidomide metabolites and their cyclized variants were designed, synthesized and characterized. In vivo antitumor activity was studied on EAC in swiss albino mice. Cytotoxicity study was carried out on HUVEC and Vero cell lines by MTT assay method. Antiangiogenic activity on Ehrlich ascites tumor (EAT) was investigated studying inhibition of formation of micro vessels by identification of CD31 antigen through immunohistochemistry. One molecule has exhibited both antitumor and antiangiogenic activity but there is no significant toxic effect on normal cell.
- Sen,Sarker,Ghosh,Mishra,Saha,Goswami,Gupta,De
-
experimental part
p. 1872 - 1878
(2012/09/22)
-
- SOLUBLE PHARMACEUTICAL FORMS OF N,N'-DIAMINODIPHENYL SULPHONE FOR OPTIMUM USE IN THE TREATMENT OF VARIOUS DISEASES
-
The present invention aims to demonstrate that a soluble pharmaceutical formulation can be prepared of N,N'-Diaminodiphenyl sulfone which is useful in the development of an ideal drug for use against cerebral infarction, epilepsy, traumatic spinal cord injury, cranio-encephalic trauma, leprosy, Pneumocystis carinii infections and any condition which requires rapid and complete absorption of the compound. A s a representative example of this application, the dissolution of N,N'-Diamino-diphenyl sulfone was evaluated as a neuroprotector in a model of acute cerebral infarction in rats. In this study, N,N'-Diamino-diphenyl sulfone showed significant prevention of brain damage, without presenting adverse effects in animals. It is also shown that the soluble pharmaceutical formulations prepared in this manner produce peak blood levels 30 minutes from oral administration and immediately via the intravenous route.
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Page/Page column 3
(2012/03/26)
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- Synthesis and biological activity of novel 1H-1,4-diazepines containing benzene sulfonyl piperazine moiety
-
The synthesis of biologically active 1H-1,4-diazepines 6a-e in good yield, from the heterocyclization reaction of [N4-(4-acetylamino) benzene sulfonyl) piperazinyl- N1-propyl]-1,3-dialkyl/aryl propane-1,3-dione 5a-e and ethylenediamine (EDA) in the presence of silica sulphuric acid (SSA) is described. The novel β-diketones/β-ketoesters 5a-e were synthesized by the condensation reaction of [N4-(4- acetylamino) benzene sulfonyl) piperazinyl-N1-1-bromopropane with various β-diketones/β-ketoesters 4a-e.All structures of the newly synthesized compounds were elucidated by elemental analysis and spectral studies.The compounds 6a-e have been screened for antimicrobial, antifungal and anthelmintic activity. Springer Science+Business Media, LLC 2010.
- Saingar, Shalini,Kumar, Rajesh,Joshi, Yogesh Chandra
-
scheme or table
p. 975 - 980
(2012/05/20)
-
- Synthesis of novel sulfanilamide-derived 1,2,3-triazoles and their evaluation for antibacterial and antifungal activities
-
A series of novel sulfanilamide-derived 1,2,3-triazole compounds were synthesized in excellent yields via 1,3-dipolar cycloaddition and confirmed by MS, IR and NMR spectra as well as elemental analyses. All the compounds were screened in vitro for their antibacterial and antifungal activities. Preliminary results indicated that some target compounds exhibited promising antibacterial potency. Especially, 4-amino-N-((1-dodecyl-1H-1,2,3-triazol-4-yl)methyl) benzenesulfonamide, N-((1-(2,4-dichlorobenzyl)- 1H-1,2,3-triazol-4-yl)methyl)-4- aminobenzenesulfonamide and 4-amino-N-((1-(2,4-difluorobenzyl)- 1H-1,2,3-triazol-4-yl)methyl) benzenesulfonamide were found to be the most potent compounds against all the tested strains except for Candida albicans (ATCC76615) and Candida mycoderma.
- Wang, Xian-Long,Wan, Kun,Zhou, Cheng-He
-
experimental part
p. 4631 - 4639
(2010/10/19)
-
- Synthesis and pharmacological evaluation of N-phenyl-acetamide sulfonamides designed as novel non-hepatotoxic analgesic candidates
-
In this paper we report the design, synthesis and pharmacological evaluation of a series of N-phenyl-acetamide sulfonamide derivatives (5a-g), planned by structural modification on the prototype paracetamol (1). In this series (5a-g), compound LASSBio-1300 (5e; ID50 = 5.81 μmol/kg) stands out as a new non-hepatotoxic analgesic drug candidate. The increase of area, volume and eletrostatic potential of paracetamol's analogues seems to be beneficial to the analgesic activity. Unlike paracetamol (1) and the other analogues (5a, 5d-g), compounds 5b and 5c presented an important anti-hypernociceptive activity associated to inflammatory pain.
- de Castro Barbosa, Maria Leticia,de Albuquerque Melo, Gabriela Muniz,da Silva, Yolanda Karla Cupertino,de Oliveira Lopes, Raquel,de Souza, Everton Tenorio,de Queiroz, Aline Cavalcanti,Smaniotto, Salete,Alexandre-Moreira, Magna Suzana,Barreiro, Eliezer J.,Lima, Lidia Moreira
-
experimental part
p. 3612 - 3620
(2009/12/09)
-
- Convenient and highly effective fluorescence sensing for Hg2+ in aqueous solution and thin film
-
A quinolinocyclodextrin, that is, MQAS-β-cyclodextrin (MQAS = N-(2-methyl-8-amino- quinolyl)-p-aminobenzene sulfonamide) was synthesized. Further experiments showed that it could form very stable stoichiometric 2:1 complex with Zn2+ in water. Significantly, the resultant quinolinocyclodextrin/Zn2+ complex showed the specific fluorescence response to Hg2+ over other metal ions, which could be readily distinguished in either aqueous solution or the PVA-based thin film. This finding would enable Zn·32 complex as a convenient and highly efficient fluorescence sensor for the detection of Hg2+.
- Liu, Yu,Yu, Miao,Chen, Yong,Zhang, Ning
-
experimental part
p. 3887 - 3891
(2009/10/02)
-
- An easy microwave-assisted synthesis of sulfonamides directly from sulfonic acids
-
(Chemical Equation Presented) An easy and handy synthesis of sulfonamides directly from sulfonic acids or its sodium salts is reported. The reaction is performed under microwave irradiation, has shown a good functional group tolerance, and is high yielding.
- De Luca, Lidia,Giacomelli, Giampaolo
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p. 3967 - 3969
(2008/09/19)
-
- Synthesis of O,O-dialkyl 2-oxo-2-(4-(selenomorpho-linosulfonyl)phenylamino) ethylphosphonate
-
A series of O,O-dialkyl 2-oxo-2-(4-(seleomorpholinosulfonyl)phenylamino) ethy lphosphonate were synthesized by reactions of 2-chloro-N-(4- (seleomorpholino sulfonyl)phenyl)acetamide with dialkylphosphite in the presence of sodium hydride. The structure of all new compounds has been confirmed by 1H NMR,31P NMR, IR, Mass spectroscopy and elemental analyses. Copyright Taylor & Francis Group, LLC.
- Wang, Fang,Hu, Liming,Li, Xiaopeng,Xu, Xuemei,Du, Hongguang
-
scheme or table
p. 610 - 616
(2009/04/11)
-
- Novel naphthalene-N-sulfonyl-D-glutamic acid derivatives as inhibitors of MurD, a key peptidoglycan biosynthesis enzyme
-
Mur ligases have essential roles in the biosynthesis of peptidoglycan, and they represent attractive targets for the design of novel antibacterials. MurD (UDP-N-acetylmuramoyl-L-alanine:D-glutamate ligase) is the second enzyme in the series of Mur ligases, and it catalyzes the addition of D-glutamic acid (D-Glu) to the cytoplasmic intermediate UDP-N-acetylmuramoyl-L-alanine (UMA). Because of the high binding affinity of D-Glu toward MurD, we synthesized and biochemically evaluated a series of N-substituted D-Glu derivatives as potential inhibitors of MurD from E. coli, which allowed us to explore the structure-activity relationships. The substituted naphthalene-N-sulfonyl-D-Glu inhibitors, which were synthesized as potential transitionstate analogues, displayed IC50 values ranging from 80 to 600 μM. In addition, the high-resolution crystal structures of MurD in complex with four novel inhibitors revealed details of the binding mode of the inhibitors within the active site of MurD. Structure-activity relationships and cocrystal structures constitute an excellent starting point for further development of novel MurD inhibitors of this structural class.
- Humljan, Jan,Kotnik, Miha,Contreras-Martel, Carlos,Blanot, Didier,Urleb, Uro?,Dessen, Andréa,?olmajer, Tom,Gobec, Stanislav
-
scheme or table
p. 7486 - 7494
(2009/11/30)
-
- Synthesis and antimicrobial evaluation of guanylsulfonamides
-
A series of guanylsulfonamides, 2-amino-9-[2-substituted-4-(4-substituted piperidin-1-sulfonyl)phenyl]-1,9-dihydropurin-6-ones, was synthesized by adopting reductive aminoformylation of 2-amino-5-nitro-6-[4-(piperidin-1-sulfonyl)phenylamino]-3H-pyrimidin- 4-one and subsequent intramolecular ring condensation as key steps. All the guanylsulfonamides were assayed for their in vitro antibacterial activities against Klebsiella pneumoniae, Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, Staphylococcus aureus, and Streptococcus faecalis, and their antifungal activities against Aspergillus flavus, Aspergillus niger, and Candida albicans. Of the guanylsulfonamides, 13e and 13f displayed better antibacterial activities than that of Norfloxacin against the bacterial strains S. aureus and S. faecalis except 13f against S. faecalis, which exhibited the activity similar to that of Norfloxacin. Against the fungal strains A. flavus and A. niger, 13g and 13h showed similar activities to that of Griseoflavin-16 except 13h against A. niger, which displayed a profound drop in the activity compared to that of Griseoflavin-16. The remarkable inhibition of the growth of the bacterial and fungal strains makes these substances promising microbial agents.
- Patel, Pratik R.,Ramalingan, Chennan,Park, Yong-Tae
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p. 6610 - 6614
(2008/09/18)
-
- NOVEL ADENOSINE A3 RECEPTOR AGONISTS
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The invention realizes that a series of sulfonamido derivatives with a conserved uronamide group at the 5' position provide superior A3 receptor affinity as well as selectivity. These new adenosine agonists are sulfonamido deritatives N-substituted with aliphatic groups (cyclic or linear) or aromatic radicals.
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Page/Page column 27
(2008/06/13)
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- Phenylenediamine urotensin-II receptor antagonists and CCR-9 antagonists
-
The present invention relates to urotensin II receptor antagonists, CCR-9 antagonists, pharmaceutical compositions containing them and their use.
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-
-
- Effects of medium and substituents on dissociation of 4,4′-disubstituted bis(benzenesulfon)imides
-
Ten 4,4′-disubstituted bis(arenesulfon)imides of the general formula XC6H4SO2NHSO2C6H 4X have been synthesized and their structures confirmed by their 1H NMR spectra. Elemental analyses are presented for the compounds not yet described. The dissociation constants of these model substances have been measured potentiometrically in pyridine, dimethylformamide, methanol, ethanol, propylene carbonate, acetone, acetonitrile, 1,2-dichloroethane and tetramethylene sulfone. The pKHA values obtained have been correlated with three sets of the Hammett substituent constants and the results have been used to discuss the solvent and substituent effects on the dissociation of the compounds studied. Sulfonimides with electron-acceptor substituents behave as rather strong acids in some solvents (pyridine, dimethylformamide, methanol and ethanol), whereas normal substituent dependences are found in other solvents. The experimental data have also been interpreted with the help of the statistical methods based on latent variables. From the calculations it follows that only the first principal component, which correlates well with the substituent constant sets adopted, is statistically significant in describing the substituent effect on the acid-base process studied.
- Ludwig, Miroslav,Stverka, Pavel
-
p. 1205 - 1214
(2007/10/03)
-
