36640-52-5Relevant academic research and scientific papers
Design, synthesis, biological evaluation, and molecular docking studies of some novel N,N-dimethylaminopropoxy-substituted aurones
Kumar, Gourav,Saroha, Bhavna,Kumar, Ramesh,Kumari, Meena,Dalal, Sunita,Kumar, Suresh
, p. 297 - 308 (2021/10/25)
In continuation of our ongoing research on the discovery of novel and potentially bioactive aurones, we have designed and synthesized some novel N,N-dimethylaminopropoxy-substituted pyrazole-based aurones 10(a-l). These pyrazole-benzofuranone hybrid compounds were characterized by using their IR, 1H-NMR, 13C-NMR, and mass spectrometry data. Compound 10c was used as a model to further explicate the structure of tilted compounds by means of 1H-1H COSY, 1H-13C HMQC, 1H-13C HMBC, 1H-1H TOCSY, 1H-1H NOSEY, DEPT-45°, DEPT-90°, and DEPT-135° NMR spectra. The comparative molecular docking study of N,N-dimethylaminopropoxy-substituted pyrazole-based aurones and standard drugs (Ampicillin and Chloramphenicol) against Bacillus subtilis (PDB: 6tzp) active site was performed to determine the binding interactions, binding energy, and orientation of the molecules at the active site of the target protein. Out of these synthesized compounds, five best analogs (10b, 10f, 10h, 10k, and 10l) of docking results were also evaluated for their in vitro antibacterial potential against Bacillus subtilis to validate the docking results.
Synthesis of lathyrane diterpenoid nitrogen-containing heterocyclic derivatives and evaluation of their anti-inflammatory activities
Wang, Wang,Xiong, Liangliang,Li, Yutong,Song, Zhuorui,Sun, Dejuan,Li, Hua,Chen, Lixia
, (2022/01/24)
As our ongoing work on lathyrane diterpenoid derivatization, three series of lathyrane diterpenoid derivatives were designed and synthesized based combination principles, including pyrazole, thiazole and furoxan moieties. Biological evaluation indicated t
Design and synthesis of novel pyrazole-phenyl semicarbazone derivatives as potential α-glucosidase inhibitor: Kinetics and molecular dynamics simulation study
Azimi, Fateme,Ghasemi, Jahan B.,Azizian, Homa,Najafi, Mohammad,Faramarzi, Mohammad Ali,Saghaei, Lotfollah,Sadeghi-aliabadi, Hojjat,Larijani, Bagher,Hassanzadeh, Farshid,Mahdavi, Mohammad
, p. 1082 - 1095 (2020/11/20)
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).
Substituted imidazole-pyrazole clubbed scaffolds: Microwave assisted synthesis and examined their in-vitro antimicrobial and antituberculosis effects
Desai, Piyush. S.,Pandya, Keyur M.,Patel, Arpan H.,Patel, Janki J.,Patel, Navin B.
, p. 574 - 582 (2021/07/25)
A series of substituted imidazole-pyrazole fused compounds were designed & fused synthesized by employing Debus-Radziszewski one-pot synthesis reaction. Azoles are an extensive and comparatively new class of synthetic compounds including imidazoles and pyrazoles. The current clinical treatment uses compounds of azole framework. Azoles act by inhibiting ergosterol synthesis pathway (a principal component of the fungal cell wall). In addition, a literature review shows that the compounds that include imidazoles and pyrazoles have significant anti-bacterial and anti-mycobacterial effects. In light of the above findings, a series of compounds with imidazole and pyrazole scaffolds were sketched and developed to examine anti-bacterial, antifungal and anti-mycobacterial activities. The structures of the synthesized compounds were characterized using1HNMR,13CNMR, elemental analysis, and MS spectral data. The target compounds were screened for their in-vitro antimicrobial activity against gram-positive and gram-negative bacterial species by disc diffusion method according to the NCCLS (National Committee for Clinical Laboratory Standards) and anti-mycobacterial activity against the Mycobacterium tuberculosis H37Rv strain. The results revealed that imidazole-pyrazole fused scaffold compounds have potential anti-bacterial, antifungal and anti-mycobacterial activities which can be further optimized to get a lead compound.
Design and synthesis of novel quinazolinone-pyrazole derivatives as potential α-glucosidase inhibitors: Structure-activity relationship, molecular modeling and kinetic study
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
, (2021/07/13)
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.
H3PO4 catalyzed one-pot synthesis of 1,3-diphenyl-1H-pyrazole-4-carbaldehyde to novel 1,3-diphenyl-1H-pyrazole-4-carbonitrile
Choudhare, Tukaram S,Netankar, Prashant D,Shirsath, Sagar E,Wagare, Devendra S
, (2021/07/10)
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.].
Novel carboxamide compound and compositions for preventing or treating metabolic diseases comprising the same
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Paragraph 0095-0099; 0126-0127; 0129-0130, (2021/09/14)
The present invention relates to a novel carboxamide compound and a composition for preventing or treating metabolic diseases comprising the same, wherein the composition is potent and selective estrogen related receptor (Estrogen-related receptor). ERR)
In vitro studies of potent aldose reductase inhibitors: Synthesis, characterization, biological evaluation and docking analysis of rhodanine-3-hippuric acid derivatives
Celestina, Stephen Kumar,Ravi, Subban,Sundaram, Kaveri
, (2020/02/22)
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.
Microwave-assisted synthesis and biological evaluation of pyrazole-4-carbonitriles as antimicrobial agents
Kumar, Anil,Kumari, Poonam,Singh, Karan,Sood, Sumit,Yadav, Ajar Nath
, (2020/05/25)
An efficient microwave-assisted method of synthesis of pyrazole-4-carbonitriles has been developed. Condensation of pyrazole-4-carbaldehydes with hydroxylamine hydrochloride followed by reaction of the resulting oximes with the Vilsmeier-Haack reagent pre-formed from phthaloyl dichloride and dimethylformamide under microwave irradiation afforded the corresponding pyrazole-4-carbonitriles in 73percent to 91percent yield. The operational simplicity, avoidance of toxic reagents such as POCl3, shorter reaction time, higher yield compared to the classical version, easy work up, and the use of the by-product in the regeneration of phthaloyl dichloride are the advantages of this methodology. All the target compounds were tested for antimicrobial activity against Gram-positive bacteria Bacillus cereus and Staphylococcus aureus; Gram-negative bacteria Escherichia coli and Yersinia enterocolitica, and the fungal species Candida albicans.
Pyrazole–coumarin and pyrazole–quinoline chalcones as potential antitubercular agents
Kumar, Gautam,Siva Krishna, Vagolu,Sriram, Dharmarajan,Jachak, Sanjay M.
, (2020/06/05)
Pyrazole, coumarin, and quinoline are medicinally important moieties. In this study, two series of novel pyrazole–coumarin chalcones and pyrazole–quinoline chalcones were synthesized using multiple-step reactions. All the synthesized compounds were well c
