- 1,3,4-Trisubstituted pyrazole analogues as promising anti-inflammatory agents
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Twenty-two 1,3,4-trisubstituted pyrazole (3a-d), (4a-d), (5a-d), (6a-l) derivatives were synthesized and structure of newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and mass spectral analysis. These compounds
- Alegaon,Alagawadi,Garg,Dushyant,Vinod
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- H3PO4 catalyzed one-pot synthesis of 1,3-diphenyl-1H-pyrazole-4-carbaldehyde to novel 1,3-diphenyl-1H-pyrazole-4-carbonitrile
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Abstract: One-pot condensation of pyrazole-4-aldehydes and hydroxylamine hydrochloride to form the corresponding oxime using formic acid as a medium and further dehydration of oxime using a catalytic amount of orthophosphoric acid to afford novel pyrazole-4-carbonitrile. This protocol serves as an ortho-phosphoric acid-catalyzed one-pot conversion of aldehyde to nitrile. Most remarkable features of this method are metal-free, cost-effective, atom efficiency with excellent yield (98–99%). This process will serve as a robust and scalable tool for the synthesis of valuable and versatile precursor (nitriles). This precursor will pave the way for the synthesis of various medicinally important valuable compounds. Graphic abstract: [Figure not available: see fulltext.].
- Choudhare, Tukaram S,Netankar, Prashant D,Shirsath, Sagar E,Wagare, Devendra S
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- Design and synthesis of novel quinazolinone-pyrazole derivatives as potential α-glucosidase inhibitors: Structure-activity relationship, molecular modeling and kinetic study
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In this study, a new series of quinazolinone-pyrazole hybrids were designed, synthesized and screened for their α-glucosidase inhibitory activity. The results of the in vitro screening indicated that all the molecular hybrids exhibited more inhibitory activity (IC50 values ranging from 60.5 ± 0.3 μM-186.6 ± 20 μM) in comparison to standard acarbose (IC50 = 750.0 ± 10.0 μM). Limited structure–activity relationship suggested that the variation in the inhibitory activities of the compounds affected by different substitutions on phenyl rings of diphenyl pyrazole moiety. The enzyme kinetic studies of the most potent compound 9i revealed that it inhibited α-glucosidase in a competitive mode with a Ki of 56 μM. Molecular docking study was performed to predict the putative binding interaction. As expected, all pharmacophoric moieties used in the initial structure design playing a pivotal role in the interaction with the binding site of the enzyme. In addition, by performing molecular dynamic investigation and MM-GBSA calculation, we investigated the difference in structural perturbation and dynamic behavior that is observed over α-glycosidase in complex with the most active compound and acarbose relative to unbound α-glycosidase enzyme.
- Azimi, Fateme,Azizian, Homa,Najafi, Mohammad,Hassanzadeh, Farshid,Sadeghi-aliabadi, Hojjat,Ghasemi, Jahan B.,Ali Faramarzi, Mohammad,Mojtabavi, Somayeh,Larijani, Bagher,Saghaei, Lotfollah,Mahdavi, Mohammad
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- Synthesis, biological evaluation, and molecular docking studies of novel pyrazole, pyrazoline-clubbed pyridine as potential antimicrobial agents
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We have prepared 15 hybrid pyrazole, pyrazoline-clubbed pyridine–containing compounds (5a-o) and tested for their antibacterial and antifungal activities for the development of potential antimicrobial agents. The structures of this novel series were chara
- Desai, Nisheeth C.,Vaja, Darshita V.,Monapara, Jahnvi D.,Manga, Vijjulatha,Vani, Tamalapakula
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p. 737 - 750
(2021/01/12)
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- Design and synthesis of novel pyrazole-phenyl semicarbazone derivatives as potential α-glucosidase inhibitor: Kinetics and molecular dynamics simulation study
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A series of novel pyrazole-phenyl semicarbazone derivatives were designed, synthesized, and screened for in vitro α-glucosidase inhibitory activity. Given the importance of hydrogen bonding in promoting the α-glucosidase inhibitory activity, pharmacophore modification was established. The docking results rationalized the idea of the design. All newly synthesized compounds exhibited excellent in vitro yeast α-glucosidase inhibition (IC50 values in the range of 65.1–695.0 μM) even much more potent than standard drug acarbose (IC50 = 750.0 μM). Among them, compounds 8o displayed the most potent α-glucosidase inhibitory activity (IC50 = 65.1 ± 0.3 μM). Kinetic study of compound 8o revealed that it inhibited α-glucosidase in a competitive mode (Ki = 87.0 μM). Limited SAR suggested that electronic properties of substitutions have little effect on inhibitory potential of compounds. Cytotoxic studies demonstrated that the active compounds (8o, 8k, 8p, 8l, 8i, and 8a) compounds are also non-cytotoxic. The binding modes of the most potent compounds 8o, 8k, 8p, 8l and 8i was studied through in silico docking studies. Molecular dynamic simulations have been performed in order to explain the dynamic behavior and structural changes of the systems by the calculation of the root mean square deviation (RMSD) and root mean square fluctuation (RMSF).
- Azimi, Fateme,Ghasemi, Jahan B.,Azizian, Homa,Najafi, Mohammad,Faramarzi, Mohammad Ali,Saghaei, Lotfollah,Sadeghi-aliabadi, Hojjat,Larijani, Bagher,Hassanzadeh, Farshid,Mahdavi, Mohammad
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p. 1082 - 1095
(2020/11/20)
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- Synthesis, characterization, anticancer and in silico studies of a pyrazole-tethered thiazolidine-2,4-dione derivative
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A new pyrazole-tethered thiazolidine-2,4-dione derivative (8) has been synthesized by the Knoevenagel condensation of 3-(4-nitrophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde (4) and 3-(2,4-dioxothiazolidin-3-yl)propanenitrile (7). The structure of the final
- Alenezi, Khalaf M.,Alshammari, Musherah M.,Haque, Ashanul,Mushtque, Md.,Rizvi, M. Moshahid Alam,Soury, Raoudha
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- In vitro studies of potent aldose reductase inhibitors: Synthesis, characterization, biological evaluation and docking analysis of rhodanine-3-hippuric acid derivatives
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Inhibitors of aldose reductase are rate-limiting enzymes and could play a key role to prevent the complications of diabetes. In our attempt to develop novel inhibitors of aldose reductase, the derivatives of rhodanine-3-hippuric acid-pyrazole hybrid were synthesized and characterised by spectral data. The biological studies reveal that all the compounds show an excellent activity against ALR2 with IC50 values ranging from 0.04 to 1.36 μM. Among these the synthesised compounds 6a-m, 6g and 6e showed specific inhibitory activity with IC50 values of 0.04 and 0.06 μM respectively against ALR2 and found to be more potent than epalrestat (IC50 = 0.87 μM), the only aldose reductase inhibitor currently used in the therapy. Molecular docking analysis using the AR-NADP+ complex as a receptor was performed with all the synthesized compounds. All the compounds exhibit a well-defined binding mode within the AR active site, similarly to previous described AR inhibitors, with the anion head group bound to the catalytic center, blocking thus its activity. By forming hydrogen bonds with Tyr48 and His110 of the protein from ALR2 (PDB ID: 2FZD), the compounds 6g and 6e interrupt the proton donation mechanism, which is necessary for the catalytic activity of ALR2.
- Celestina, Stephen Kumar,Ravi, Subban,Sundaram, Kaveri
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- Synthesis and computational studies of highly selective inhibitors of human recombinant tissue non-specific alkaline phosphatase (h-TNAP): A therapeutic target against vascular calcification
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In this study, we have discovered small druglike molecules as selective inhibitors of human tissue-nonspecific alkaline phosphatase (h-TNAP), an enzyme critical for the regulation of extracellular matrix calcification. The upregulation of h-TNAP is associated with various pathologies particularly the vascular calcification (VC). Selective inhibition of h-TNAP over h-NPP1 may serve as a useful therapeutic strategy against vascular calcification. A series of novel triazolyl pyrazole derivatives (10a-y) in which thiol bearing triazole moiety as the zinc binding functional group was introduced to a pyrazole based pharmacophore was synthesized and evaluated as potent and selective inhibitors of h-TNAP over h-NPP1. The biological screening against h-TNAP, h-IAP, h-NPP1 and h-NPP3 showed that many of the synthesized compounds are selective inhibitors of TNAP. Particularly, the compounds 10a-h, 10j, 10m-q, 10u, 10w and 10x displayed high potency and complete selectivity towards h-TNAP over h-NPP1. Compound 10q emerged as a highly potent inhibitor (IC50 = 0.16 μM or 160 nM) against h-TNAP with 127-fold increased inhibition compared to levamisole. On the other hand, compound 10e was found to be most selective inhibitor against the tested APs and NPPs (IC50 = 1.59 ± 0.36 μM). Binding sites architecture analysis, molecular-docking and molecular dynamics simulations (MDS), revealed the basis for h-TNAP and h-IAP ligand selectivity as well as selectivity towards h-TNAP over h-NPP1. These newly discovered inhibitors are believed to represent valuable lead structures to further streamline the generation of candidate compounds to target VC.
- Abida Ejaz, Syeda,Andleeb, Hina,Farman, Muhammad,Hameed, Shahid,Hussain, Muzammal,Iqbal, Jamshed,Sevigny, Jean,Yasinzai, Masoom,Zhang, Jiancun
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- Microwave-Assisted Synthesis and Antimicrobial Activity of Novel Pyrazole–Indanone Hybrid Analogs
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Abstract: A simple and efficient microwave-assisted protocol has been developed for the synthetic of a series of novel pyrazole–indanone hybrid analogs. The target compounds have been synthesized by the Claisen–Schmidt condensation of different 1,3-diphenyl-1H-pyrazole-4-carbaldehydes with 2,3-dihydro-1H-inden-1-one in the presence of potassium hydroxide. The compounds were characterized by IR, 1H and 13C NMR, and mass spectra and were found to exhibit potent antimicrobial activity in vitro.
- Sundergoud, Sh.,Swamy, M. Kumara,Veerasomaiah, P.,Venkatesh, N.
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p. 1635 - 1639
(2020/10/22)
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- Pyrazolylphenanthroimidazole heterocycles: Synthesis, biological and molecular docking studies
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The synthesis of a series of novel pyrazolylphenanthroimidazoles 6a-6j has been accomplished utilizing a multi-step synthetic protocol, and characterized through physical and spectral techniques. Among them, the molecules possessing para-bromo (6d), para-methyl (6f) and para-nitro (6j) phenyl substituents on the pyrazole scaffold displayed similar anti-inflammatory activity and the one with no substituents on the aryl unit (6a) exhibited the highest anti-inflammatory profile. While investigating the DPPH radical scavenging activity, the synthesized chemical entity with a para-methoxyphenyl group attached at the pyrazole structural motif (6i) revealed the highest activity when compared to the other synthesized molecules. Furthermore, the evaluation of cytotoxic activity of the synthesized molecule (6a) exerted significant activity against both the pancreatic cell lines such as AsPC1 and SW1990. Besides, while performing the molecular docking studies of 6a with B-cell lymphoma 2, an appreciable binding affinity (-9.04 kcal mol-1) has been observed. The results of the present examination imply that these chemical entities could be used as efficient intermediates for the construction of biopertinent molecules. This journal is
- Sivaramakarthikeyan, Ramar,Iniyaval, Shunmugam,Lim, Wei-Meng,Hii, Ling-Wei,Mai, Chun-Wai,Ramalingan, Chennan
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p. 19612 - 19622
(2020/12/04)
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- Synthesis and evaluation of pyrazole-incorporated monocarbonyl curcumin analogues as antiproliferative and antioxidant agents
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A series of pyrazole-incorporated monocarbonyl analogues of curcumin were synthesized via Clasien–Schimidt-type condensation and subsequently screened for in vitro antiproliferative and antioxidant activity. The analogues 4c, 5d, 5e, 5g, 6e, and 6f showed
- Nagargoje, Amol A.,Akolkar, Satish V.,Siddiqui, Madiha M.,Bagade, Aditi V.,Kodam, Kisan M.,Sangshetti, Jaiprakash N.,Damale, Manoj G.,Shingate, Bapurao B.
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p. 1658 - 1665
(2019/03/29)
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- Discovery of 1,3-diphenyl-1H-pyrazole derivatives containing rhodanine-3-alkanoic acid groups as potential PTP1B inhibitors
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Two series of 1,3-diphenyl-1H-pyrazole derivatives containing rhodanine-3-alkanoic acid groups were identified as competitive protein tyrosine phosphatase 1B (PTP1B) inhibitors. Among the compounds studied, IIIv was found to have the best in vitro inhibition activity against PTP1B (IC50 = 0.67 ± 0.09 μM) and the best selectivity (9-fold) between PTP1B and T-cell protein tyrosine phosphatase (TCPTP). Molecular docking studies demonstrated that compounds IIIm, IIIv and IVg could occupy simultaneously at both the catalytic site and the adjacent pTyr binding site. These results provide novel lead compounds for the design of inhibitors of PTP1B as well as other PTPs.
- Sun, Liangpeng,Wang, Peipei,Xu, Lili,Gao, Lixin,Li, Jia,Piao, Huri
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p. 1187 - 1193
(2019/03/26)
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- Probing the high potency of pyrazolyl pyrimidinetriones and thioxopyrimidinediones as selective and efficient non-nucleotide inhibitors of recombinant human ectonucleotidases
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With the aim to discover novel, efficient and selective inhibitors of human alkaline phosphatase and nucleotide pyrophosphatase enzymes, two new series of pyrazolyl pyrimidinetriones (PPTs) (6a–g) and thioxopyrimidinediones (PTPs) (6h–n) were synthesized in good chemical yields using Knoevenagel condensation reaction between pyrazole carbaldehydes (4a–g) and pharmacologically active N-alkylated pyrimidinetrione (5a) and thioxopyrimidinedione (5b). The inhibition potential of the synthesized hybrid compounds was evaluated against human alkaline phosphatase (h-TNAP and h-IAP) and ectonucleotidase (h-NPP1 and h-NPP3) enzymes. Most of the tested analogs were highly potent with a variable degree of inhibition depending on the functionalized hybrid structure. The detailed structure-activity relationship (SAR) of PPT and PTP derivatives suggested that the compound with unsubstituted phenyl ring from PPT series led to selective and potent inhibition (6a; IC50 = 0.33 ± 0.02 μM) of h-TNAP, whereas compound 6c selectively inhibited h-IAP isozyme with IC50 value of 0.86 ± 0.04 μM. Similarly, compounds 6b and 6h were identified as the lead scaffolds against h-NPP1 and h-NPP3, respectively. The probable binding modes for the most potent inhibitors were elucidated through molecular docking analysis. Structure-activity relationships, mechanism of action, cytotoxic effects and druglikeness properties are also discussed.
- Andleeb, Hina,Hameed, Shahid,Ejaz, Syeda Abida,Khan, Imtiaz,Zaib, Sumera,Lecka, Joanna,Sévigny, Jean,Iqbal, Jamshed
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- Synthesis and biological evaluation of thiazolidine-2,4-dione-pyrazole conjugates as antidiabetic, anti-inflammatory and antioxidant agents
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A series of fourteen novel thiazolidine-2,4-dione derivatives clubbed with pyrazole moiety were synthesized via four step reaction procedure. Reactions were monitored by thin layer chromatography and were characterized by physicochemical and spectrophotometric (IR, Mass, 1HNMR and 13CNMR) analysis. The spectral data were in good agreement with their structures. The title compounds were docked against peroxisome proliferated activated receptors (PPAR-γ) and alpha-amylase and further evaluated for in vivo and in vitro antidiabetic, in vitro anti-inflammatory and antioxidant activities. Compound GB14 exhibited significant blood glucose lowering activity and was also found to be active inhibitor of alpha-amylase. Compound GB7 was found to be potent anti-inflammatory agent in terms of reducing inflammatory markers (TNF-α, IL-β, MDA) and also showed antioxidant activity to good extent. Therefore, these compounds may be considered as promising candidates for the development of new antidiabetic agents.
- Bansal, Garima,Singh, Shamsher,Monga, Vikramdeep,Thanikachalam, Punniyakoti Veeraveedu,Chawla, Pooja
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- Design, synthesis and cytotoxicity evaluation of pyrazolyl pyrazoline and pyrazolyl aminopyrimidine derivatives as potential anticancer agents
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In an attempt to find bio-active heterocyclic analogues, a series of novel 1-(5-(3-(aryl)-1-phenyl-1H-pyrazol-4-yl)-3-(pyridin-3-yl)-4,5-dihydropyrazol-1-yl)ethanones 5a–i and 4-(3-(aryl)-1-phenyl-1H-pyrazol-4-yl)-6-(pyridine-3-yl)pyrimidin-2-amines 6a–i were designed, synthesized, and evaluated for their in vitro cytotoxicity against a panel of human cancer cell lines namely, HeLa (human cervix), NCI-H460 (human lung), PC-3 (human prostate), and NIH-3T3 (mouse embryo fibroblasts) cell lines. Most of these compounds exhibited moderate to good cytotoxicity against the tested cancer cell lines and weak toxicity against normal cell line. Analogs 5f, 5g, 5i, 6b–g showed significant cytotoxicity as compared to the standard drug etoposide. The compound 6g exhibited superior activity with IC50 value of 5.47 ± 0.44 μM against Hela cancer cell line.
- Alam, Raquib,Alam, Aftab,Panda, Amulya K.,Rahisuddin
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p. 560 - 570
(2017/10/13)
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- Synthesis and antimicrobial evaluation of some heterocyclic compounds from 3-Aryl-1-phenyl-1H-pyrazole-4-carbaldehydes
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A new series of chalcones, pyrazolinyl-pyrazoles, pyrazole-4-carbaldehyde oximes, pyrazole-4-carbonitriles, 5-pyrazolyl-1,2,4-Triazolidine-3-Thiones, and Knoevenagel condensation products was synthesized from 3-Aryl-1-phenyl-1H-pyrazole-4-carbaldehydes. Most reactions were carried out either without solvent or in the presence of water as a green solvent. The structure of synthesized compounds was characterized by spectral and elemental analysis. The synthesized compounds were tested in vitro for their antimicrobial activity against Escherichia coli, Staphylococcus aureus, and Candida albicans in comparison with imipenem (intravenous β-lactam antibiotic) and clotrimazole (antifungal medication) as reference drugs by using the agar diffusion technique. 3-Aryl-1-phenyl-1H-pyrazole-4-carbonitriles 8b, 8c, and 8d showed significant antifungal activity against the fungus C. albicans.
- Ramadan, El Sayed,Sharshira, Essam M.,El Sokkary, Ramadan I.,Morsy, Noussa
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p. 389 - 397
(2018/05/30)
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- Design, Synthesis, and Cytotoxicity Evaluation of 3-(5-(3-(aryl)-1-phenyl-1H-pyrazol-4-yl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)pyridine and 5-(3-(aryl)-1-phenyl-1H-pyrazol-4-yl)-3-(pyridin-3-yl)-4,5-dihydropyrazole-1-carbaldehyde Derivatives as Potential Anticancer Agents
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In an attempt to find bio-active small molecules, a series of novel 3-(5-(3-(aryl)-1-phenyl-1H-pyrazol-4-yl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)pyridine 5a–i and 5-(3-(aryl)-1-phenyl-1H-pyrazol-4-yl)-3-(pyridin-3-yl)-4,5-dihydropyrazole-1-carbaldehyde 6a–i were designed, synthesized, and evaluated for their in vitro cytotoxic activity against a panel of human cancer cell lines namely; HeLa (human cervix), NCI-H460 (human lung), PC-3 (human prostate), and NIH-3T3 (mouse embryo fibroblasts) normal cell line. Most of these compounds exhibited moderate to good cytotoxic activity against the tested cancer cell lines and weak toxicity against normal cell line. Analogues 5b, 5f, 5g, 6b, and 6g showed significant cytotoxicity as compared to standard drug etoposide. Among all the synthesized compounds, compound 6g displayed superior cytotoxicity with an IC50 value of 7.98 ± 1.08 μM for Hela cancer cell line.
- Alam, Raquib,Alam, Md. Aftab,Panda, Amulya K.,Rahisuddin
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p. 1812 - 1821
(2017/05/29)
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- Design, synthesis, biological evaluation and molecular modelling studies of novel diaryl substituted pyrazolyl thiazolidinediones as potent pancreatic lipase inhibitors
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A series of novel diaryl substituted pyrazolyl 2,4-thiazolidinediones were synthesized via reaction of appropriate pyrazolecarboxaldehydes with 2,4-thiazolidinedione (TZD) and nitrobenzyl substituted 2,4-thiazolidinedione. The resulting compounds were screened in vitro for pancreatic lipase (PL) inhibitory activity. Two assay protocols were performed viz., methods A and B using p-nitrophenyl butyrate and tributyrin as substrates, respectively. Compound 11e exhibited potent PL inhibitory activity (IC50?=?4.81?μM and Xi50?=?10.01, respectively in method A and B), comparable to that of the standard drug, orlistat (IC50?=?0.99?μM and Xi50?=?3.72). Presence of nitrobenzyl group at N-3 position of TZD and nature of substituent at para position of phenyl ring at C-3 position of pyrazole ring notably affected the PL inhibitory activity of the tested compounds. Enzyme inhibition kinetics of 11e revealed its reversible competitive inhibition, similar to that of orlistat. Molecular docking studies validated the rationale of pharmacophoric design and are in accordance to the in vitro results. Compound 11e exhibited a potential MolDock score of ?153.349?kcal/mol. Further, the diaryl pyrazolyl wing exhibited hydrophobic interactions with the amino acids of the hydrophobic lid domain. Moreover, the carbonyl group at 2nd position of the TZD ring existed adjacent to Ser 152 (≈3??) similar to that of orlistat. A 10?ns molecular dynamics simulation of 11e–PL complex revealed a stable binding conformation of 11e in the active site of PL (Maximum RMSD?≈?3??). The present study identified novel thiazolidinedione based leads with promising PL inhibitory activity. Further development of the leads might result in potent PL inhibitors.
- S.N.C., Sridhar,Bhurta, Deendyal,Kantiwal, Dharmvir,George, Ginson,Monga, Vikramdeep,Paul, Atish T.
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supporting information
p. 3749 - 3754
(2017/07/27)
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- 2-(3,4-Dichlorophenylimino)-5-((3-(p-substitutedphenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidin-4-one as an Antibacterial, Antifungal and Antimycobacterial Agent
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2-(3,4-Dichlorophenylimino)-5-((3-(p-substitutedphenyl)-1-phenyl-1H-pyrazol-4-yl)methylene) thiazolidin-4-one has been selected as a target bio-active molecules. Newly synthesized compounds were screened with Eschericha coli (MTCC 443), Pseudomonas aeruginosa (MTCC 1688), Staphylococcus aureus (MTCC 96), Streptococcus pyogenes (MTCC 442) for antibacterial, Candida albicans (MTCC 227), Aspergillus niger (MTCC 282), Aspergillus clavatus (MTCC 1323) for antifungal activity and H37Rv for antimycobacterial activity. Compounds 3a, 3c, 3d, 3e, and 3h are potentially active against Staphylococcus aureus, while 3h is active against C.?albicans. Compounds 3d and 3f are active against H37Rv for mycobacterium tuberculosis. Other possesses moderate to good activity. The structures of synthesized compounds were firmly established by well-defined elemental analyses (C, H, N, S/O) and spectral analysis technique likes, IR, 1H NMR and GC–MS.
- Brahmbhatt, Harshad,Bhatt, Anjani K.,Das, Arun K.,Paul, Parimal,Sharma, Sangita
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p. 2838 - 2843
(2017/09/26)
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- Development of new pyrazole hybrids as antitubercular agents: Synthesis, biological evaluation and molecular docking study
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Objective: Synthesis of new 1, 3-diphenyl pyrazole derivatives 9(a-f) and 10(a-f) using molecular hybridization approach and evaluation of their antitubercular and cytotoxic studies. Methods: The structures of synthesized compounds were confirmed by 1H NMR, 13C NMR and mass spectra. The antitubercular activity of compounds and standard drugs were assessed against Mycobacterium tuberculosis using Microplate alamar blue assay (MABA). The cytotoxic activities were performed by Sulforhodamine B (SRB) assay. The molecular docking and in silico ADME prediction studies were also performed by using Schrodinger. Results: The results reveal that compounds 9c, 9d, 10c and 10d exhibited substantial antitubercular potential with MIC10. The molecular docking study was performed to study the binding orientation and affinity of synthesized compounds for InhA enzyme. Conclusion: The study explored that 1, 3-diphenyl pyrazole hybrid coupled with well-known antitubercular drugs could be a potential lead for antitubercular agents. In silico molecular docking, study helps to identify their corresponding intermolecular ligand-protein interactions with target enzyme. Also, ADME prediction studies revealed that the compounds were in acceptable range to have good pharmacokinetic parameters.
- Shaikh, Sameer I.,Zaheer, Zahid,Mokale, Santosh N.,Lokwani, Deepak K.
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- Pyrazole based NLOphores: Synthesis, photophysical, DFT, TDDFT studies
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A series of pyrazole based D-π-A derivatives have been synthesized from 3-(4-nitrophenyl)-1-pheny-1H-pyrazole-3-carbaldehyde with series of active methylene compounds. The dyes were well characterized by FT-IR, 1H NMR, 13C NMR, eleme
- Lanke, Sandip K.,Sekar, Nagaiyan
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p. 116 - 127
(2016/01/25)
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- Design, synthesis, cytotoxicity, HuTopoIIα inhibitory activity and molecular docking studies of pyrazole derivatives as potential anticancer agents
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In an attempt to find potential anticancer agents, a series of novel ethyl 4-(3-(aryl)-1-phenyl-1H-pyrazol-4-yl)-2-oxo-6-(pyridin-3-yl)cyclohex-3-enecarboxylates 5a-i and 5-(3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-3-(pyridin-3-yl)-4,5-dihydropyrazole-1-carbothioamides 6a-i were designed, synthesized and evaluated for their topoisomerase IIα inhibitory activity and in vitro cytotoxicity against a panel of cancerous cell lines (MCF-7, NCI-H460, HeLa) and a normal cell line (HEK-293T). Molecular docking studies of all the synthesized compounds into the binding site of topoisomerase IIα protein (PDB ID: 1ZXM) were performed to gain a comprehensive understanding into plausible binding modes. These compounds were also screened for in silico drug-likeliness properties on the basis of the absorption, distribution, metabolism and excretion (ADME) prediction. Among all the synthesized compounds, analogue 5d showed superior cytotoxicity with an IC50 value of 7.01?±?0.60?μM for HeLa, 8.55?±?0.35?μM for NCI-H460 and 14.31?±?0.90 for MCF-7 cancer cell lines. Further, compound 5d showed 70.82% inhibition of topoisomerase IIα at a concentration of 100?μM with maximum docking score of ?8.24. Results of ADME prediction revealed that most of these compounds showed in silico drug-likeliness properties within the ideal range.
- Alam, Raquib,Wahi, Divya,Singh, Raja,Sinha, Devapriya,Tandon, Vibha,Grover, Abhinav,Rahisuddin
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- Design, synthesis and cytotoxicity evaluation of novel (E)-3-(3-aryl-1-phenyl-1H-pyrazol-4-yl)-1-(pyridin-3-yl)prop-2-en-1-ones as anticancer agents
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(E)-3-(3-Aryl-1-phenyl-1H-pyrazol-4-yl)-1-(pyridin-3-yl)prop-2-en-1-ones 4a-i have been synthesized and evaluated for their in vitro cytotoxicity against a panel of three human cancer cell lines Caco-2, MIA PaCa-2, MCF-7 and a normal NIH-3T3 cell line. Compound 4g is cytotoxic with the IC50 value of 15.32±0.62 μm against the Caco-2 cell line.
- Alam, Raquib,Alam, Md. Aftab,Panda, Amulya K.,Uddin, Rahis
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p. 221 - 225
(2016/08/30)
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- Identification of novel pyrazole-rhodanine hybrid scaffolds as potent inhibitors of aldose reductase: Design, synthesis, biological evaluation and molecular docking analysis
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In an effort to develop a new class of potent aldose reductase inhibitors, a series of 1,3-diarylpyrazole assimilated 3-substituted 4-oxo-2-thioxo-1,3-thiazolidines (9a-n) was designed, and synthesized in good to excellent yields by a pharmacophore integr
- Andleeb, Hina,Tehseen, Yildiz,Ali Shah, Syed Jawad,Khan, Imtiaz,Iqbal, Jamshed,Hameed, Shahid
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p. 77688 - 77700
(2018/06/22)
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- Synthesis of new pyrazolyl-1,3-diazabicyclo[3.1.0]hexe-3-ene derivatives
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A series of new of photochromic 1,3-diazabicyclo[3.1.0]hex-3-ene derivatives based on the skeleton of five-membered pyrazole moiety have been synthesized and characterized by spectral techniques, as well as their photochromic properties were examined under UV light irradiation in various solutions. All these newly synthesized compounds showed good photochromic properties in the both solution and solid states. The UV-Visible spectral analysis of the corresponding pyrazolyl bicyclic aziridines established structure-photochromic behavior relationships.
- Kiyani, Hamzeh,Albooyeh, Fereshteh,Fallahnezhad, Saied
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p. 163 - 169
(2015/03/30)
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- Identification of pyrazole derivative as an antiviral agent against chikungunya through HTVS
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Structure based High-throughput Virtual Screening (HTVS) of ChikV nsP2 protease (PDB: 3TRK) with two publicly available database ZINC12 and BindingDB has been carried out to identify suitable inhibitors for the treatment of chikungunya infection. HTVS pro
- Jadav, Surender Singh,Sinha, Barij Nayan,Pastorino, Boris,De Lamballerie, Xavier,Hilgenfeld, Rolf,Jayaprakash, Venkatesan
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p. 292 - 301
(2015/04/14)
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- New 4-fluoroalkyl substituted N-phenylpyrazoles: Synthesis promoted by DAST and multinuclear NMR analysis
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This paper reports a synthetic and NMR spectroscopic studies of two new series of 4-fluorinated 1,3,5-substituted 1H-pyrazoles. Firstly, an efficient synthesis of new series of 3-aryl-4-(di)fluoromethyl-1H-1-phenylpyrazoles, where [aryl = Ph, 4-NO2/
- Bonacorso, Helio G.,Pittaluga, Everton P.,Porte, Liliane M.F.,Junges, Andrizia F.,Libero, Francieli M.,Zanatta, Nilo,Martins, Marcos A.P.
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- Pyrazole clubbed triazolo[1,5-a]pyrimidine hybrids as an anti-tubercular agents: Synthesis, in vitro screening and molecular docking study
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A series of novel pyrazole linked triazolo-pyrimidine hybrids were synthesized and evaluated for their anti-tuberculosis activity against M.tb H37Rv strain. Some of the screened entities rendered promising anti-tb activity (MIC: 0.39 μg/mL) and were found non toxic against Vero cells (IC50: ≥20 μg/mL). Further, the docking study against wild type InhA enzyme of Mycobacterium tuberculosis using Glide reproduced the most active inhibitors (J21 and J27) with lowest binding energies and highest Glide XP scores demonstrating efficient binding to the active pocket. Additionally, the enzyme inhibition assay and ADME prediction of the active proved to be an attest to the possibility of developing compound J27 as a potent anti-tubercular lead.
- Bhatt, Jaimin D.,Chudasama, Chaitanya J.,Patel, Kanuprasad D.
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supporting information
p. 7711 - 7716
(2015/12/20)
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- Unexpected Metal-Free Fluorination and Oxidation at the C-4 Position of Pyrazoles Promoted by Selectfluor
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Metal-free electrophilic fluorination, promoted by Selectfluor, of pyrazoles with methylene groups (CH2X), in which XA =A OH, OMe, F, N3, and NHMe at the C-4 position furnished the 4-fluoro-pyrazole products from unexpected C-C bond cleavage, at moderate to good yields. Otherwise, under the same reaction conditions, when XA =A NEt2 or SPr, the oxidation product 4-formyl-pyrazole was obtained.
- Bonacorso, Helio G.,Pittaluga, Everton P.,Porte, Liliane M. F.,Libero, Francieli M.,Junges, Andrizia F.,Zanatta, Nilo,Martins, Marcos A. P.
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p. 2009 - 2013
(2015/09/01)
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- Design and synthesis of novel 2-phenyl-5-(1,3-diphenyl-1H-pyrazol-4-yl)-1, 3,4-oxadiazoles as selective COX-2 inhibitors with potent anti-inflammatory activity
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A novel series of 2-phenyl-5-(1,3-diphenyl-1H-pyrazol-4-yl)-1,3,4- oxadiazoles were designed and synthesized for selective COX-2 inhibition with potent anti-inflammatory activity. Among the compounds tested, 9g (2-(3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)-5-phenyl-1,3,4-oxadiazole) was found to be the most potent inhibitor of COX-2 with IC of 0.31 μM showing promising degree of anti-inflammatory activity in the carrageenan-induced rat paw edema model with ED of 74.3 mg/kg. The lead compound 9g further showed suppression of acetic acid-induced writhes comparable to that of aspirin and gastro-sparing profile superior to the aspirin. Molecular docking analysis displayed higher binding affinity of ligands towards COX-2 than COX-1.
- Bansal, Sumit,Bala, Manju,Suthar, Sharad Kumar,Choudhary, Shivani,Bhattacharya, Shoumyo,Bhardwaj, Varun,Singla, Sumit,Joseph, Alex
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p. 167 - 174
(2014/05/20)
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- Curcumin-I Knoevenagel's condensates and their Schiff's bases as anticancer agents: Synthesis, pharmacological and simulation studies
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Pyrazolealdehydes (4a-d), Knoevenagel's condensates (5a-d) and Schiff's bases (6a-d) of curcumin-I were synthesized, purified and characterized. Hemolysis assays, cell line activities, DNA bindings and docking studies were carried out. These compounds were lesser hemolytic than standard drug doxorubicin. Minimum cell viability (MCF-7; wild) observed was 59% (1.0 μg/mL) whereas the DNA binding constants ranged from 1.4 × 10 3 to 8.1 × 105 M-1. The docking energies varied from -7.30 to -13.4 kcal/mol. It has been observed that DNA-compound adducts were stabilized by three governing forces (Van der Wall's, H-bonding and electrostatic attractions). It has also been observed that compounds 4a-d preferred to enter minor groove while 5a-d and 6a-d interacted with major grooves of DNA. The anticancer activities of the reported compounds might be due to their interactions with DNA. These results indicated the bright future of the reported compounds as anticancer agents.
- Ali, Imran,Haque, Ashanul,Saleem, Kishwar,Hsieh, Ming Fa
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p. 3808 - 3820
(2013/07/25)
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- Diaryl pyrazole-4-carbaldehyde benzoylhydrazones metal complexes: Synthesis and their antibacterial and antioxidant screening
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Various heterocyclic ligands [1,3-diarylpyrazole-4-carbaldehyde benzoyl-hydrazones] and their metal complexes with Cu2+, Ni2+, Co2+, Pb 2+, Zn2+ and Fe2+ have been synthesized, characterized and screened for their antibact
- Nasrullah, Muhammad,Khan, Misbahul Ain,Khan, Muhammad Naeem,Humphrey, Mark G. Humphrey,Nasim, Faizul Hassan,Chaudhry, Faryal,Abidi, Moeena Ghazal,Farooq, Umar,Munawar, Munawar Ali
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p. 419 - 423
(2013/02/22)
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- Synthesis of novel 1,3-diaryl pyrazole derivatives bearing rhodanine-3-fatty acid moieties as potential antibacterial agents
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In the present study, a series of 1,3-diaryl pyrazole derivatives bearing rhodanine-3-fatty acid moieties were synthesized and their antimicrobial activities were tested against various Gram-positive and Gram-negative bacteria. 1,3-diaryl-4-formylpyrazoles were synthesized as key intermediates following a Vilsmeier-Haack strategy. Several compounds with an MIC of 2 μg/mL, exhibited stronger antibacterial activity against the methicillin-resistant Staphylococcus aureus (MRSA) than the controls. None of the compounds showed any activity against Gram-negative bacteria.
- Xu, Li-Li,Zheng, Chang-Ji,Sun, Liang-Peng,Miao, Jing,Piao, Hu-Ri
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scheme or table
p. 174 - 178
(2012/03/26)
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- Synthesis, biological evaluation, and molecular docking studies of N,1,3-triphenyl-1H-pyrazole-4-carboxamide derivatives as anticancer agents
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A series of N,1,3-triphenyl-1H-pyrazole-4-carboxamide derivatives have been designed, synthesized and evaluated for their potential antiproliferation activity and Aurora-A kinase inhibitory activity. Among all the compounds, compound 10e possessed the most potent biological activity against HCT116 and MCF-7 cell lines with IC50 values of 0.39 ± 0.06 μM and 0.46 ± 0.04 μM, respectively, which were comparable to the positive control. Compound 10e also exhibited significant Aurora-A kinase inhibitory activity (IC50 = 0.16 ± 0.03 μM). Docking simulation was performed to position compound 10e into the active site of Aurora-A kinase, in order to get the probable binding model for further study. The results of Western-blot assay demonstrated that compound 10e possessed good Aurora-A kinase inhibitory activity against HCT116. Based on the preliminary results, it is deduced that compound 10e with potent Aurora-A kinase inhibitory activity may be a potential anticancer agent.
- Li, Xi,Lu, Xiang,Xing, Man,Yang, Xian-Hui,Zhao, Ting-Ting,Gong, Hai-Bin,Zhu, Hai-Liang
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supporting information; experimental part
p. 3589 - 3593
(2012/07/16)
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- Synthesis, biological evaluation and molecular docking studies of 3-(1,3-diphenyl-1H-pyrazol-4-yl)-N-phenylacrylamide derivatives as inhibitors of HDAC activity
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In present study, a series of 3-(1,3-diphenyl-1H-pyrazol-4-yl)-N- phenylacrylamide derivatives (5a-8d) were designed, synthesized, and evaluated for HDAC inhibition and tumor cell antiproliferation. All of these compounds are reported for the first time,
- Li, Xi,Liu, Jia-Lin,Yang, Xian-Hui,Lu, Xiang,Zhao, Ting-Ting,Gong, Hai-Bin,Zhu, Hai-Liang
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experimental part
p. 4430 - 4436
(2012/08/29)
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- Synthesis and antimicrobial evaluation of some novel 2-(4- chlorophenylimino) thiazolidin-4-one derivatives
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A series of 2-(4-chlorophenylimino)-5-((3-(p-substituted phenyl)-1-phenyl-1H-pyrazol-4-yl) methylene) thiazolidin-4-one (3a-h) compounds were prepared from the 2-(4-chlorophenylimino) thiazolidin-4-one (1) and 1-phenyl-3-(p-substituted phenyl)-1H-pyrazole-4-carbaldehyde (2a-h). All compounds were characterized by elemental (C, H, N) analysis and spectral (FT-IR, 1H NMR and GC-MS) analysis. These newly synthesized compounds were screened for their antibacterial and antifungal activities. Antimicrobial activity was observed and evaluated against the bacterial strains like Eschericha coli (MTCC 443), Pseudomonas aeruginosa (MTCC 1688), Staphylococcus aureus (MTCC 96), Streptococcus pyogenes (MTCC 442) and against the fungal strains like Candida albicans (MTCC 227), Aspergillus niger (MTCC 282) and Aspergillus clavatus (MTCC 1323). All the synthesized compounds were found to possess moderate to excellent antimicrobial activity against above selected strains.
- B'Bhatt,Sharma
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scheme or table
p. 341 - 347
(2012/09/05)
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- Efficient and rapid synthesis of highly functionalized novel symmetric 1,4-dihydropyridines using glacial acetic acid as solvent
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A new series of 1,4-dihydropyridines bearing a pyrazole moiety in the 4-position were synthesized by a variation of the classical Hantzsch synthesis. The reaction of 1,3-diphenyl-1H-pyrazole-4-carbaldehyde 4a-n with 3-amino crotononitrile in the presence of glacial acetic acid afforded novel 3,5-dicyano-2,6-dimethyl 1,4-dihydropyridines 5a-n. The procedure has short reaction time (15-20 min), easy workup, and good yield of product. The structures of all synthesized compounds were well characterized by mass, infrared, 1H and 13C NMR, and elemental analysis.
- Thakrar, Shailesh,Bavishi, Abhay,Bhavsar, Dhairya,Parekh, Shrey,Vala, Hardev,Radadiya, Ashish,Parmar, Manisha,Savant, Mahesh,Shah, Anamik
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scheme or table
p. 3269 - 3278
(2012/09/08)
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- Synthesis, characterization and biological activity of some new carbostyril bearing 1H-pyrazole moiety
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In this study, 16 new 4-pyrazolyl-N-arylquinoline-2,5-dione 4 have been synthesized by the multicomponent reaction of pyrazole-4-carbaldehyde 1, Meldrum's acid 2 and 3-aryl-5,5-disubstitutedcyclohex-2-enone 3. The structures of compounds 4 were established by the combined use of 1HNMR, 13C NMR, FT-IR and mass spectra. All the 16 compounds were tested in vitro for their bacterial and fungal activity against a list of human pathogens, namely, Bacillus subtilis, Clostridium tetani, Streptococcus pneumoniae, Salmonella typhi, Vibrio cholerae, Escherichia coli, Aspergillus fumigatus and Candida albicans, using broth microdilution MIC (minimum inhibitory concentration) method. Some of the compounds were found to be the most effective analogs against the tested bacterial and fungal strains. Springer Science+Business Media, LLC 2011.
- Thumar, Nilesh J.,Patel, Manish P.
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p. 1751 - 1761
(2012/11/13)
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- Synthesis and antimicrobial activity of 5-((3-aryl-1-phenyl-1Hpyrazol-4-yl) methylene)thiazolidine-2,4-diones
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A series of 5-((3-aryl-1-phenyl-1H-pyrazol-4- yl)methylene)thiazolidine-2, 4-diones was synthesized by Knoevenagel condensation of various 3-aryl-1-phenyl- 1H-pyrazole-4-carbaldehydes (1a-h) with thiazolidine-2,4- dione (2) in ethanol in the presence of piperidine. All compounds were screened for their in vitro antibacterial (Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Escherichia coli) activity and compared with the commercially available antibiotic, ciprofloxacin. All compounds showed good activity against gram-positive bacteria, however, none of the compounds were found to be effective against gram-negative bacteria. Compound 3g was found to be most potent member among all the compounds showing MIC of 16 μg/ml against S. aureus and 32 μg/ml against B. subtilis. All the synthesized compounds were also tested for their in vitro antifungal (Aspergillus niger and A. flavus) activity and compared with commercially available fluconazole. They showed excellent antifungal activity. Compounds 3b, 3e, 3f and 3g were active against both fungi showing more than 60% inhibition. Compound 3e was found to be superior to the reference drug.
- Prakash, Om,Aneja, Deepak K.,Lohan, Poonam,Hussain, Khalid,Arora, Sanjiv,Sharma, Chetan,Aneja, Kamal R.
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p. 2961 - 2968,8
(2020/08/20)
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- An efficient one pot synthesis and antimicrobial activity of novel S-alkylisothiosemicarbazone and imidazolidinone derivatives of pyrazole carbaldehyde
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S-Alkylisothiosemicarbazone and imidazolidinone derivatives were synthesised from pyrazole 4-carbaldehyde in a one pot reaction. The synthesised compounds were characterized by IR, 1H NMR, 13C NMR, mass and elemental analysis. Most of the synthesised compounds showed antimicrobial activity against S. Aureus, B. subtilis, E. coli, P. aeruginos, A. Niger and C. albicans.
- Patil, Sachin V.,Gaikwad, Nitin D.,Bobade, Vivek D.
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p. 590 - 594
(2013/01/15)
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- Synthesis and antimicrobial activity of some new N-substituted quinoline derivatives of 1H-pyrazole
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A new series of 32 derivatives of 4-pyrazolyl-N-(hetero)arylquinoline 5a-p and 6a-p were synthesized by a one-pot base-catalyzed cyclocondensation reaction of 1-phenyl-3-(hetero)aryl-pyrazole-4-carbaldehyde 1a-h, malononitrile 2, and 3-(hetero)aryl-5,5-disubstitutedcyclohex-2-enone 3a-b or 4a-b, respectively. All the synthesized compounds were characterized by elemental analysis, FT-IR, 1H-NMR, and 13C-NMR spectral data. All the synthesized compounds were screened, against six bacterial pathogens, namely Bacillus subtilis, Clostridium tetani, Streptococcus pneumoniae, Salmonella typhi, Vibrio cholerae, Escherichia coli, and antifungal activity, against two fungal pathogens Aspergillus fumigatus and Candida albicans, using broth microdilution MIC method. Some of the compounds were found to be more or equipotent against most of the employed strains than commercially available drugs as evident from the screening data. Quinoline derivatives are known to exhibit a wide range of biological activities. Therefore, a series of some new 1,4-di(hetero)aryl quinoline derivatives bearing a 1H-pyrazole nucleus have been synthesized and were evaluated for their antimicrobial activities against a panel of human pathogens. Copyright
- Thumar, Nilesh J.,Patel, Manish P.
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scheme or table
p. 91 - 101
(2011/09/21)
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- Synthesis of novel pyrazolic analogues of chalcones and their 3-aryl-4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-1-phenyl-1H-pyrazole derivatives as potential antitumor agents
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Novel (E)-1-aryl-3-(3-aryl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-ones 5/6 (pyrazolic chalcones) were synthesized from a Claisen-Schmidt reaction of 3-aryl-1-phenylpyrazol-4-carboxaldehydes 4 with several acetophenone derivatives 1. Subsequently, the microwave-assisted cyclocondensation reaction of chalcones 5/6 with hydrazine afforded the new racemic 3-aryl-4-(3-aryl-4,5-dihydro-1H- pyrazol-5-yl)-1-phenyl-1H-pyrazoles 7 or their N-acetyl derivatives 8 and 9 when reactions where carried out in DMF or acetic acid, respectively. Several of these compounds were screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines, where 5c and 9g showed remarkable activity mainly against leukemia (K-562 and SR), renal cancer (UO-31) and non-small cell lung cancer (HOP-92) cell lines, with the most important GI50 values ranging from 0.04 to 11.4 μM, from the in vitro assays.
- Insuasty, Braulio,Tigreros, Alexis,Orozco, Fabian,Quiroga, Jairo,Abonia, Rodrigo,Nogueras, Manuel,Sanchez, Adolfo,Cobo, Justo
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supporting information; scheme or table
p. 4965 - 4974
(2010/09/05)
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- Synthesis and antibacterial activity of l, 3-diaryl-4-cyanopyrazoles
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A mild, short and simple method for the small scale synthesis of pharmaceutical important l, 3-diaryl-4- cyanopyrazoles 3 is reported from acetophenone arylhydrazones 1 through a two step reaction. All the title compounds have been subjected to in vitro a
- Prakash, Om,Pundeer, Rashmi,Ranjan, Pooja,Pannu, Kamaljeet,Dhingra, Yogita,Aneja
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experimental part
p. 563 - 568
(2009/12/24)
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- One-pot synthesis of some new semicarbazone, thiosemicarbazone, and hydrazone derivatives of 1-phenyl-3-arylpyrazole-4-carboxaldehyde from acetophenone phenylhydrazones using Vilsmeier-Haack reagent
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Semicarbazone derivatives 3 of 1,3-diphenylpyrazole-4-carboxaldehyde have been synthesized in high yields through a one-pot procedure involving acetophenone phenylhydrazones 1 subjected to Vilsmeier double formylation and workup under new conditions (i.e., treatment with semicarbazide followed by sodium bicarbonate). This method is even suitable for preparing other derivatives (i.e., thiosemicarbazones 4 and hydrazones 5) in high yields. Copyright Taylor & Francis Group, LLC.
- Pundeer, Rashmi,Ranjan, Pooja,Pannu, Kamaljeet,Prakash, Om
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experimental part
p. 316 - 324
(2009/05/09)
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- Synthesis of some new 2-(3-aryl-1-phenyl-4-pyrazolyl)benzoxazoles using hypervalent iodine mediated oxidative cyclization of schiff's bases
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Ten new 2-(3-aryl-1-phenyl-4-pyrazolyl)benzoxazoles have been synthesized by oxidative intramolecular cyclization of the corresponding Schiff's bases using iodobenzene diacetate in methanol as an oxidant.
- Prakash, Om,Pannu, Kamaljeet,Kumar, Ajay
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- One-pot synthesis of oxime derivatives of 1,3-diphenylpyrazole-4- carboxaldehydes from acetophenone phenylhydrazones using vilsmeier-haack reagent
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A one-pot synthesis of oxime derivatives 3a-3f of 1-phenyl-3-arylpyrazole- 4-carboxaldehydes has been accomplished by the Vilsmeier-Haack reaction of acetophenone phenylhydrazones 1a-1f under a new workup procedure. Copyright Taylor & Francis Group, LLC.
- Prakash, Om,Pannu, Kamaljeet,Naithani, Rajesh,Kaur, Harpreet
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p. 3479 - 3485
(2007/10/03)
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