NewN-phenylacetamide-linked 1,2,3-triazole-tethered coumarin conjugates: Synthesis, bioevaluation, and molecular docking study

被引：27

作者：

Akolkar, Satish, V ^{[1
]}

Nagargoje, Amol A. ^{[1
,2
]}

Shaikh, Mubarak H. ^{[1
,3
]}

Warshagha, Murad Z. A. ^{[1
]}

Sangshetti, Jaiprakash N. ^{[4
]}

Damale, Manoj G. ^{[5
]}

Shingate, Bapurao B. ^{[1
]}

机构：

[1] Dr Babasaheb Ambedkar Marathwada Univ, Dept Chem, Aurangabad 431004, Maharashtra, India

[2] Khopoli Municipal Council Coll, Dept Chem, Khopoli, India

[3] Radhabai Kale Mahila Mahavidyalaya, Dept Chem, Ahmednagar, India

[4] YB Chavan Coll Pharm, Dept Pharmaceut Chem, Dr Rafiq Zakaria Campus, Aurangabad, Maharashtra, India

[5] Srinath Coll Pharm, Dept Pharmaceut Chem, Aurangabad, Maharashtra, India

来源：

ARCHIV DER PHARMAZIE | 2020年 / 353卷 / 11期

关键词：

ADME properties; antifungal activity; antioxidant activity; molecular docking; triazole-coumarin conjugates; ANTITUBERCULAR AGENTS SYNTHESIS; CLICK CHEMISTRY; BIOLOGICAL EVALUATION; 1,3,4-OXADIAZOLE DERIVATIVES; ANTIMICROBIAL ACTIVITY; TRIAZOLE DERIVATIVES; DRUG DISCOVERY; ANTIOXIDANT; DESIGN; HYBRIDS;

D O I：

10.1002/ardp.202000164

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of new 1,2,3-triazole-tethered coumarin conjugates linked byN-phenylacetamide was efficiently synthesizedviathe click chemistry approach in excellent yields. The synthesized conjugates were evaluated for their in vitro antifungal and antioxidant activities. Antifungal activity determination was carried out against fungal strains such asCandida albicans,Fusarium oxysporum,Aspergillus flavus,Aspergillus nigerandCryptococcus neoformans. Compounds7b,7d,7e,8band8edisplayed higher potency than the standard drug miconazole, with lower minimum inhibitory concentration values. Also, compound7aexhibited potential radical scavenging activity as compared with the standard antioxidant butylated hydroxytoluene. In addition, a molecular docking study of the newly synthesized compounds was carried out, and the results showed a good binding mode at the active site of the fungal (C. albicans) P450 cytochrome lanosterol 14 alpha-demethylase enzyme. Furthermore, the synthesized compounds were also tested for ADME properties, and they demonstrated potential as good candidates for oral drugs.

引用

页数：13

共 63 条

[1] Click Chemistry: 1,2,3-Triazoles as Pharmacophores [J].

Agalave, Sandip G. ;

Maujan, Suleman R. ;

Pore, Vandana S. .

CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) :2696-2718

[2] Synthesis and pharmacological evaluation of some novel 2-(5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(coumarin-3-yl)thiazoles [J].

Aggarwal, Ranjana ;

Kumar, Sunil ;

Kaushik, Pawan ;

Kaushik, Dhirender ;

Gupta, Girish Kumar .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 62 :508-514

[3] New N-phenylacetamide-incorporated 1,2,3-triazoles: [Et3NH][OAc]-mediated efficient synthesis and biological evaluation [J].

Akolkar, Satish V. ;

Nagargoje, Amol A. ;

Krishna, Vagolu S. ;

Sriram, Dharmarajan ;

Sangshetti, Jaiprakash N. ;

Damale, Manoj ;

Shingate, Bapurao B. .

RSC ADVANCES, 2019, 9 (38) :22080-22091

[4] Synthesis of 4-aryl-1,2,3-triazolyl appended natural coumarin-related compounds with antiproliferative and radical scavenging activities and intracellular ROS production modification [J].

Bistrovic, A. ;

Stipanicev, N. ;

Opacak-Bernardi, T. ;

Jukic, M. ;

Martinez, S. ;

Glavas-Obrovac, Lj. ;

Raic-Malic, S. .

NEW JOURNAL OF CHEMISTRY, 2017, 41 (15) :7531-7543

[5] 1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview [J].

Bozorov, Khurshed ;

Zhao, Jiangyu ;

Aisa, Haji A. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2019, 27 (16) :3511-3531

[6]

Burits M, 2000, PHYTOTHER RES, V14, P323, DOI 10.1002/1099-1573(200008)14:5<323::AID-PTR621>3.0.CO

[7]

2-Q

[8] Peniisocoumarins A-J: Isocoumarins from Penicillium commune QQF-3, an Endophytic Fungus of the Mangrove Plant Kandelia candel [J].

Cai, Runlin ;

Wu, Yingnan ;

Chen, Senhua ;

Cui, Hui ;

Liu, Zhaoming ;

Li, Chunyuan ;

She, Zhigang .

JOURNAL OF NATURAL PRODUCTS, 2018, 81 (06) :1376-1383

[9]

Dai ZC, 2015, ORG BIOMOL CHEM, V13, P477, DOI [10.1039/c4ob01758g, 10.1039/C4OB01758G]

[10] Recent developments of C-4 substituted coumarin derivatives as anticancer agents [J].

Dandriyal, Jyoti ;

Singla, Ramit ;

Kumar, Manvendra ;

Jaitak, Vikas .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 119 :141-168

← 1 2 3 4 5 6 7 →