- Novel Schiff base-bridged multi-component sulfonamide imidazole hybrids as potentially highly selective DNA-targeting membrane active repressors against methicillin-resistant Staphylococcus aureus
-
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
-
-
- Inhibition of carbonic anhydrase II by sulfonamide derivatives
-
A series of sulfonamide derivatives were synthesized, and the enzyme inhibitory activity of the synthesized compounds on carbonic anhydrase II was evaluated. Through molecular docking studies, it was found that compounds 1b, 1e, 2a, 2b, 3a have a strong binding affinity to carbonic anhydrase II. The IC50 values of the four compounds 1e, 2b, 3a, and 3b were lower than that of the positive control drug acetazolamide. What’s more, the compounds had a high inhibitory activity for A549 lung cancer cell growth, among them, 1e and 3a could inhibit both carbonic anhydrase II and lung cancer cell proliferation.
- Xuan,Zhan,Zhang,Li,Zheng
-
p. 412 - 415
(2021/11/22)
-
- Synthesis and Antibacterial Activity of Sulfanilamides Containing Sterically Hindered Phenol Fragments
-
Abstract: New sulfanilamide derivatives containing sterically hindered phenol fragments have been synthesized via modification of the amino group by reaction with 3,5-di-tert-butyl-4-hydroxybenzyl acetate and diazotization followed by diazo coupling with
- Bukharov, S. V.,Burilov, A. R.,Mukmeneva, N. A.,Nikitina, E. V.,Nugumanova, G. N.,Tagasheva, R. G.
-
p. 1621 - 1627
(2021/12/13)
-
- SAR study of 4-arylazo-3,5-diamino-1: H -pyrazoles: identification of small molecules that induce dispersal of Pseudomonas aeruginosa biofilms
-
By screening of a collection of 50 000 small-molecule compounds, we recently identified 4-arylazo-3,5-diamino-1H-pyrazoles as a novel group of anti-biofilm agents. Here, we report a SAR study based on 60 analogues by examining ways in which the pharmacoph
- Andersen, Jens B.,Givskov, Michael,Hultqvist, Louise D.,Jakobsen, Tim H.,Jansen, Charlotte U.,Nielsen, Thomas E.,Nilsson, Martin,Qvortrup, Katrine M.,Tolker-Nielsen, Tim,Uhd, Jesper
-
p. 1868 - 1878
(2021/12/22)
-
- NaHSO3-Mediated Direct Synthesis of Sulfinic Esters from Sulfonyl Hydrazides under Transition-Metal-Free Conditions
-
We have developed a protocol for the NaHSO3-promoted esterification of sulfonyl hydrazides with alcohols for the synthesis of sulfinic esters. Various sulfonyl hydrazides could be converted to the corresponding sulfinic esters in good to high yields. The merits of this protocol include mild transition-metal-free reaction conditions, an inexpensive and available reagent, and operational simplicity. Controlled experiments reveal that this transformation probably undergoes via a radical pathway. (Figure presented.).
- Zhang, Guofu,Fan, Qiankun,Wang, Huimin,Zhao, Yiyong,Ding, Chengrong
-
supporting information
p. 833 - 837
(2020/12/07)
-
- One-pot synthesis of sulfonylhydrazones from sulfonyl chloride, hydrazine hydrate and vinyl azide in water
-
A facile and eco-friendly protocol for the synthesis of sulfonylhydrazones from sulfonyl chlorides, hydrazine hydrate and vinyl azides was developed. The unique advantage of this approach is that desired products can be obtained efficiently in water, which meets the requirements of green chemistry and provides good perspectives for the sustainable production of new drug candidate. Also, this reaction proceeded in moderate to good yields with a wide tolerance of functional groups.
- Luo, Mengqiang,Wang, Hai,Ren, Xiaorong,Lu, Ruijuan,Qi, Chenze,Zhang, Yaohong,Shen, Runpu
-
p. 2713 - 2722
(2021/03/19)
-
- Inhibitory Evaluation and Molecular Docking Analysis of Benzenesulfonamides on Carbonic Anhydrase II
-
Abstract: Sulfonamides is an important class of compounds, which can be used as carbonic anhydrase inhibitors. Nine different benzenesulfonamide compounds were synthesized, and their inhibitory effects on carbonic anhydrase II were studied by esterase method and molecular docking. The results showed that compounds (IId)–(IIg) with nitro and acetamide groups on the benzene ring exhibited excellent carbonic anhydrase II inhibitory activities. Molecular docking showed that compared with the control inhibitor acetazolamide, the compounds (IId)–(IIg) docked at the carbonic anhydrase II active site and showed higher binding energy and stronger binding ability. The physical and chemical properties of all compounds were studied by Molinspiration, which showed outstanding drug-like properties and ADME properties. Cytotoxicity assay results showed that compounds (IIe) and (IIf) were almost non-toxic to HepG2 and RAW264.7 cells. In conclusion, the compounds (IIe) and (IIf) have a certain application prospect as new inhibitors of carbonic anhydrase II.
- Zhang,Wei,Liu,Wu,Xuan
-
p. 261 - 269
(2021/03/23)
-
- TBAB-catalyzed 1,6-conjugate sulfonylation of paraquinone methides: A highly efficient approach to unsymmetrical gem-diarylmethyl sulfones in water ?
-
A highly efficient sulfonylation of para-quinone methides with sulfonyl hydrazines in water has been developed on the basis of the mode involving a tetrabutyl ammonium bromide (TBAB)-promoted sulfa-1,6-conjugated addition pathway. This reaction provides a green and sustainable method to synthesize various unsymmetrical diarylmethyl sulfones, showing good functional group tolerance, scalability, and regioselectivity. Further transformation of the resulting diarylmethyl sulfones provides an efficient route to some functionalized molecules.
- Liu, Zhang-Qin,You, Peng-Sheng,Zhang, Liang-Dong,Liu, Da-Qing,Liu, Sheng-Shu,Guan, Xiao-Yu
-
supporting information
(2020/02/11)
-
- Electrochemically Induced Synthesis of Sulfonylated N-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides
-
Sulfonylated N-unsubstituted enamines were synthesized through a chain of chemical and electrochemical transformations via sulfonylation of vinyl azides. The disclosing of the N-unsubstituted enamines synthesis was based on a unique property of the azido group, which is its ability to eliminate the N2 molecule. Furthermore, a formal paradox is observed: A double bond reacts and a double bond is retained. Electrosynthesis proceeded in an undivided cell equipped with a graphite anode and a stainless steel cathode; NH4I was used as a supporting electrolyte.
- Mulina, Olga M.,Zhironkina, Nataliya V.,Paveliev, Stanislav A.,Demchuk, Dmitry V.,Terent'Ev, Alexander O.
-
supporting information
p. 1818 - 1824
(2020/03/04)
-
- Synthesis of calix[4]azacrown substituted sulphonamides with antioxidant, acetylcholinesterase, butyrylcholinesterase, tyrosinase and carbonic anhydrase inhibitory action
-
A series of novel calix[4]azacrown substituted sulphonamide Schiff bases was synthesised by the reaction of calix[4]azacrown aldehydes with different substituted primary and secondary sulphonamides. The obtained novel compounds were investigated as inhibitors of six human (h) isoforms of carbonic anhydrases (CA, EC 4.2.1.1). Their antioxidant profile was assayed by various bioanalytical methods. The calix[4]azacrown substituted sulphonamide Schiff bases were also investigated as inhibitors of acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and tyrosinase enzymes, associated with several diseases such as Alzheimer, Parkinson, and pigmentation disorders. The new sulphonamides showed low to moderate inhibition against hCAs, AChE, BChE, and tyrosinase enzymes. However, some of them possessed relevant antioxidant activity, comparable with standard antioxidants used in the study.
- Akocak, Suleyman,Boga, Mehmet,Kalay, Erbay,Lolak, Nebih,Nocentini, Alessio,Oguz, Mehmet,Supuran, Claudiu T.,Yilmaz, Mustafa
-
p. 1215 - 1223
(2020/05/27)
-
- Arylsulfonylhydrazone induced apoptosis in MDA-MB-231 breast cancer cells
-
Background: Breast cancer is the most frequent cancer among women. Chemotherapy is necessary for treating metastatic disease and represents an important therapeutic approach, although antineoplastic drugs have high toxicity and may be limited by the development of drug resistance. These problems impose an urgent need to discover new anticancer agents and, so, arylsulfonylhydrazone analogues were designed, synthesized, and evaluated with regard to their cytotoxic activity against breast cancer cells in order to identify novel potential antitumor agents. Methods: Synthesis was performed as previously described by Fernandes and co-workers. Cytotoxicity of sulfonylhydrazones against MDA-MB-231, MCF-7 and 3T3 cells was evaluated by MTT method. Apoptotic effects was verified by Annexin-V/PI assay, Hoechst stain and propidium iodide stain. Molecular modeling was executed using Spartan’10 version 1.1.0. Geometry optimization was performed by the MMFF, PM6 and Hartree-Fock 3-31G* methods and electronic and lipophilic properties were computed. Results: Thirteen analogues were synthesized, which 3f and 4f were cytotoxic against evaluated breast cancer cells. The most promising compound, 3f, showed IC50 values equal to 104.6 and 142.4 μM for MDA-MB-231 and MCF-7, respectively. 3f induced apoptosis, causing phosphatidylserine externalization, pyknosis, and cell cycle arrest in the G0/G1 phase in MDA-MB-231 breast cancer cells. Furthermore, 3f was selective for tumor cells when compared to 3T3 fibroblasts. Structure-activity relationship suggests that introduction of a benzodioxol group increased cytotoxicity and superior lipophilicity may be related to superior activity. Conclusion: Sulfonylhydrazone analogues presented good activity against breast cancer cells by inducing apoptosis and might be a promising scaffold to further molecular modifications persuing more effective antitumoral agents.
- Fernandes, Thais Batista,de Azevedo, Ricardo Alexandre,Yang, Rosania,Teixeira, Sarah Fernandes,Trossini, Gustavo Henrique Goulart,Barbuto, José Alexandre Marzag?o,Ferreira, Adilson Kleber,Parise-Filho, Roberto
-
p. 1288 - 1298
(2018/11/01)
-
- Synthesis, Molecular Modeling, and Evaluation of Novel Sulfonylhydrazones as Acetylcholinesterase Inhibitors for Alzheimer's Disease
-
Alzheimer's disease (AD) is the most common type of dementia and related to the degeneration of hippocampal cholinergic neurons, which dramatically affects cognitive ability. Acetylcholinesterase (AChE) inhibitors are employed as drugs for AD therapy. Three series of sulfonylhydrazone compounds were designed, and their ability to inhibit AChE was evaluated. Fifteen compounds were synthesized and twelve of them had IC50 values of 0.64–51.09 μM. The preliminary structure–activity relationships indicated that the methylcatechol moiety and arylsulfonyl substituents generated better compounds than both the benzodioxole and alkylsulfonyl chains. Molecular dynamics studies of compound 6d showed that the interaction with the peripheral binding site of AChE was similar to donepezil, which may explain its low IC50 (0.64 μM). Furthermore, the drug-likeness of 6d suggests that the compound may have appropriate oral absorption and brain penetration. Compound 6d also presented antiradical activity and was not cytotoxic to LL24 cells, suggesting that this compound might be considered safe. Our findings indicate that arylsulfonylhydrazones may be a promising scaffold for the design of new drug candidates for the treatment of AD.
- Fernandes, Thais B.,Cunha, Micael R.,Sakata, Renata P.,Candido, Thalita M.,Baby, André R.,Tavares, Maurício T.,Barbosa, Euzébio G.,Almeida, Wanda P.,Parise-Filho, Roberto
-
-
- Base-mediated tandem sulfonylation and oximation of alkenes in water
-
A base-mediated bifunctionalization of alkenes for the synthesis of α-sulfonylethanone oximes was developed in water under metal-free conditions. This reaction features a wide substrate scope and facile starting materials to afford the desired products in high yields.
- Wang, Bin,Tang, Lin,Liu, Liyan,Li, Yanan,Yang, Yu,Wang, Zhiyong
-
supporting information
p. 5794 - 5799
(2017/12/26)
-
- Gold-Catalyzed Dehydrazinative C(sp)–S Coupling Reactions of Arylsulfonyl Hydrazides with Ethynylbenziodoxolones for Accessing Alkynyl Sulfones
-
A gold(III)-catalyzed dehydrazinative coupling reaction between arylsulfonyl hydrazides and ethynylbenziodoxolone reagents was realized for the synthesis of alkynyl sulfones. The scope and versatility of the reaction were demonstrated by the efficient synthesis of 23 derivatives with diverse structural features.
- Shinde, Popat S.,Patil, Nitin T.
-
p. 3512 - 3515
(2017/07/04)
-
- Oxysulfonylation of Alkenes with Sulfonyl Hydrazides under Transition-Metal-Free Conditions
-
A novel method to synthesise β-keto sulfones is demonstrated by Br?nsted acid promoted oxysulfonylation of alkenes with sulfonyl hydrazides under transition-metal-free conditions. The reaction selectively affords structurally diverse β-keto sulfones in good to excellent yields in a 9:1 mixture of acetonitrile/water.
- Liu, Congrong,Ding, Lianghui,Guo, Guang,Liu, Weiwei
-
supporting information
p. 910 - 912
(2016/03/01)
-
- Palladium-catalyzed allylation of sulfonyl hydrazides with alkynes to synthesize allylic arylsulfones
-
A novel method for the construction of allyl arylsulfone derivatives was developed by palladium catalyzed allylation of sulfonyl hydrazides with alkynes. A series of structurally diverse allyl arylsulfones can be regioselectively synthesized in high yields under mild conditions.
- Lu, Chuan-Jun,Chen, Hong,Chen, Dong-Kai,Wang, Hong,Yang, Zhen-Ping,Gao, Jianrong,Jin, Hongwei
-
p. 10833 - 10839
(2016/12/06)
-
- Design, synthesis, molecular docking and 3D-QSAR studies of potent inhibitors of enoyl-acyl carrier protein reductase as potential antimycobacterial agents
-
In order to develop a lead antimycobacterium tuberculosis compound, a series of 52, novel pyrrole hydrazine derivatives have been synthesized and screened which target the essential enoyl-ACP reductase. The binding mode of the compounds at the active site of enoyl-ACP reductase was explored using surflex-docking method. The binding model suggests one or two hydrogen bonding interactions between pyrrole hydrazones and InhA enzyme. Highly active compound 5r (MIC 0.2 μg/mL) showed hydrogen bonding interactions with Tyr158 and NAD+ in the same manner as those of ligands PT70 and triclosan. The CoMFA and CoMSIA models generated with database alignment were the best in terms of overall statistics. The predictive ability of the CoMFA and CoMSIA models was determined using a test set of 13 compounds, which gave predictive correlation coefficients (rpred2) of 0.896 and 0.930, respectively.
- More, Uttam A.,Joshi, Shrinivas D.,Aminabhavi, Tejraj M.,Gadad, Andanappa K.,Nadagouda, Mallikarjuna N.,Kulkarni, Venkatrao H.
-
p. 199 - 218
(2014/01/06)
-
- Catalyst-free sulfonylation of activated alkenes for highly efficient synthesis of mono-substituted ethyl sulfones in water
-
A catalyst-free sulfonylation reaction of activated alkenes with sulfonyl hydrazides was efficiently developed under mild and environmentally benign conditions, in water without any ligand or additive. The reaction gave a range of structurally diverse mono-substituted ethyl sulfones with excellent yields, in which the by-product was nitrogen. the Partner Organisations 2014.
- Yang, Yu,Tang, Lin,Zhang, Sheng,Guo, Xuefeng,Zha, Zhenggen,Wang, Zhiyong
-
supporting information
p. 4106 - 4109
(2014/10/15)
-
- Synthesis and antiviral activities of novel acylhydrazone derivatives targeting HIV-1 capsid protein
-
HIV-1 capsid protein (CA) plays important roles in the viral replication cycle. A number of acylhydrazone derivatives that act as inhibitors of HIV-1 CA assembly, were designed and synthesized. The synthesized compounds were tested for their antiviral activities and cytotoxicities using CEM cells. Some derivatives also were assayed for their ability to inhibit HIV-1 CA assembly in vitro. Among them, compounds 14f and 14i display the most promising potency with EC50 values of 0.21 and 0.17 μΜ, respectively.
- Tian, Baohe,He, Meizi,Tang, Shixing,Hewlett, Indira,Tan, Zhiwu,Li, Jiebo,Jin, Yinxue,Yang, Ming
-
scheme or table
p. 2162 - 2167
(2009/12/25)
-
- An efficient synthesis of sulfonylhydrazides and sulfonylsemicarbazides by utilizing alumina as a catalyst
-
Sulfonyl hydrazides and sulfonyl semicarbazides are readily prepared by the reacting of hydrazine derivatives with sulfonyl chlorides in the presence of basic alumina under solvent-free conditions. Reaction of a sulfonyl chloride with t-butylcarbazate, followed by hydrolysis provides the corresponding sulfonyl hydrazides in higher yield and shorter time than previously reported.
- Safaei-Ghomi, Javad
-
p. 1561 - 1563
(2008/09/16)
-
- A facile and general method for the preparation of α-disulfones (R1SO2SO2R2)
-
Dialkyl, diaryl and alkyl aryl disulfones are easily prepared by oxidation of N,N'-disulfonylhydrazines with nitric acid. The method is compatible with a wide variety of substituents (R1,R2) on the sulfur atoms.
- Bartmann
-
p. 490 - 496
(2007/10/02)
-
- SALICYLIC ACID SULFONYL DERIVATIVES AND RELATED COMPOUNDS
-
Salicylic acid-5-sulfonohydrazide (3) has been condensed with β-dicarbonyl compounds to form pyrazoles (5).With ethyl acetoacetate, tri- and hexafluoropentane-2,4-dione the hydrazones (4) were obtained; although the former did cyclise in the presence of potassium carbonate-magnesium sulfate.With hexane-2,5-dione the pyrrole (7) was formed and not the pyridazine (8).Acylation of salicylic acid-5- and p-acetamidobenzene-sulfonohydrazides was examined; mono-acetates, benzoates and p-toluenesulfonates and diacetates are described, but other pure diacyl derivatives could not be i solated.Reaction with succinic and maleic anhydrides gave the corresponding amic acids (9, 10), and their cyclisation to pyridazines (11) was examined; only the maleamic acid (10) was converted to the pyridazine (11).Maleic hydrazide (14) by condensation with p-acetamido-benzenesulfonyl chloride gave the O-sulfonyl pyridazine (15). 5-Chlorosalicylic acid-3-sulfonohydrazide (18) was prepared and characterized as the acetone and cyclohexanone hydrazones (19); but attempts to make aromatic hydrazones gave the azines (20). 5-Chlorosalicylic acid-3-sulfonyl azide (21) reacted with norbornene and triphenylphosphine to give the aziridine (22) and the phosphinimine (23).
- Cremlyn, Richard,Swinbourne, Frederick,Plant, Stephen,Saunders, David,Sinderson, Colin
-
p. 323 - 332
(2007/10/02)
-