Synthesis and Pharmacological Screening of Difluorophenyl Pyrazole Chalcone Conjugates as Antifungal, Anti-Inflammatory, and Antioxidant Agents

被引：10

作者：

Jadhav, S. Y. ^{[1
]}

Peerzade, N. A. ^{[2
]}

Hublikar, M. G. ^{[2
]}

Varpe, B. D. ^{[3
]}

Kulkarni, A. A. ^{[3
]}

Bhosale, R. B. ^{[2
]}

机构：

[1] DBF Dayanand Coll Arts & Sci, Dept Chem, Solapur 413002, Maharashtra, India

[2] PAH Solapur Univ, Sch Chem Sci, Organ Chem Res Lab, Solapur 413002, Maharashtra, India

[3] DKSSs Inst Pharmaceut Sci & Res, Dept Pharmaceut Chem, Pune 413130, Maharashtra, India

来源：

RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY | 2020年 / 46卷 / 06期

关键词：

difluorophenyl pyrazole chalcones; antifungal; anti-inflammatory; antioxidant; molecular docking; in silico ADMET; PEG MEDIATED SYNTHESIS; IN-VITRO ANTIOXIDANT; ANTIMICROBIAL ACTIVITY; MEDICINAL CHEMISTRY; DERIVATIVES; FLUORINE; ANALOGS;

D O I：

10.1134/S1068162020060102

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A new series of difluoro phenyl pyrazole chalcone was prepared by utilizing PEG 400 as a catalyst and investigated for their antifungal, anti-inflammatory, and antioxidant activity. The compounds 3-[3-(4-bromo-phenyl)-1-phenyl-1H-pyrazol-4-yl]-1-(2,4-difluloro-phenyl)-propenone (IVc), 1-(2,4-difluoro-phenyl)-3-[3-(4-methyl-phenyl)-1-phenyl-1H-pyrazol-4-yl]-propenone (IVd), 1-(2,4-difluoro-phenyl)-3-[3-(4-methoxy-phenyl)-1-phenyl-1H-pyrazol-4-yl]-propenone (IVe), and 1-(2,4-difluoro-phenyl)-3-(1,3-diphenyl-1H-pyrazol-4-yl)-propenone (IVg) exhibited promising antifungal activity at MIC of 25 and 50 mu g/mL against selected human pathogenic fungi. Synthesized compounds 1-(2,4-difluoro-phenyl)-3-[3-(4-methoxy-phenyl)-1-phenyl-1H-pyrazol-4-yl]-propenone (IVe), 1-(2,4-difluoro-phenyl)-3-[3-(4-methyl-phenyl)-1-phenyl-1H-pyrazol-4-yl]-propenone (IVd), 1-(2,4-difluoro-phenyl)-3-(1,3-diphenyl-1H-pyrazol-4-yl)-propenone (IVg) and 1-(2,4-difluoro-phenyl)-3-[3-(4-fluoro-phenyl)-1-phenyl-1H-pyrazol-4-yl]-propenone (IVa) showed good anti-inflammatory activities comparable to the standard drug diclofenac sodium. Compounds 1-(2,4-difluoro-phenyl)-3-[3-(4-methoxy-phenyl)-1-phenyl-1H-pyrazol-4-yl]-propenone (IVe), 1-(2,4-difluoro-phenyl)-3-[3-(4-methyl-phenyl)-1-phenyl-1H-pyrazol-4-yl]-propenone (IVd) and 1-(2,4-difluoro-phenyl)-3-(1,3-diphenyl-1H-pyrazol-4-yl)-propenone (IVg) showed good hydrogen peroxide scavenging potential as compared to the butylated hydroxyl toluene. The conjugates 1-(2,4-difluoro-phenyl)-3-[3-(4-methoxy-phenyl)-1-phenyl-1H-pyrazol-4-yl]-propenone (IVe), 1-(2,4-difluoro-phenyl)-3-(1,3-diphenyl-1H-pyrazol-4-yl)-propenone (IVg), and 1-(2,4-difluoro-phenyl)-3-[3-(4-methyl-phenyl)-1-phenyl-1H-pyrazol-4-yl]-propenone (IVd) found more potent than standard ascorbic acid in DPPH radical scavenging assay as well as ferrous reducing power assay. The conjugates showed good interactions with the target protein in docking study.

引用

页码：1128 / 1135

页数：8

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