Microwave-assisted synthesis, antioxidant and antimicrobial evaluation of 2-indolinone-based bis-1,2,3-triazole derivatives

被引:36
作者
Ashok, Dongamanti [1 ]
Gundu, Srinivas [1 ]
Aamate, Vikas Kumar [1 ]
Devulapally, Mohan Gandhi [1 ]
机构
[1] Osmania Univ, Dept Chem, Green & Med Chem Lab, Hyderabad 500007, Andhra Pradesh, India
关键词
Bis-1,2,3-triazole; 2-Indolinone; Antioxidant; Antimicrobial; Microwave irradiation; Solvent-free; Click chemistry; BIOLOGICAL EVALUATION; SCAVENGING PROPERTIES; CLICK CHEMISTRY; AGENTS; 1,2,3-TRIAZOLES; INHIBITION; HYBRIDS; DESIGN; DAMAGE; MONO;
D O I
10.1007/s11030-017-9791-2
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 series of 2-indolinone-based bis-1,2,3-triazole derivatives have been synthesized in excellent yields via microwave-assisted, copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) reaction of O-, N-propargylated indolinone derivatives with in situ generated organic azides. The antioxidant activity of the synthesized compounds was evaluated by DPPH, NO and radical scavenging methods. Among the compounds screened for antioxidant activity, compounds 5e, 5f and 5o showed excellent radical scavenging activity more than the standard drugs ascorbic acid and BHT. The synthesized compounds were evaluated for their antimicrobial activity against gram-positive and gram-negative bacterial and fungal strains. Compounds 5g, 5h, 5n, 5q and 5r were found to be the most promising microbial growth inhibitory molecules.
引用
收藏
页码:57 / 70
页数:14
相关论文
共 43 条
[21]   The isatin-Schiff base copper(II) complex Cu(isaepy)2 acts as delocalized lipophilic cation, yields widespread mitochondrial oxidative damage and induces AMP-activated protein kinase-dependent apoptosis [J].
Filomeni, Giuseppe ;
Piccirillo, Sara ;
Graziani, Ilaria ;
Cardaci, Simone ;
Da Costa Ferreira, Ana M. ;
Rotilio, Giuseppe ;
Ciriolo, Maria R. .
CARCINOGENESIS, 2009, 30 (07) :1115-1124
[22]   ANALYSIS OF NITRATE, NITRITE, AND [N-15]-LABELED NITRATE IN BIOLOGICAL-FLUIDS [J].
GREEN, LC ;
WAGNER, DA ;
GLOGOWSKI, J ;
SKIPPER, PL ;
WISHNOK, JS ;
TANNENBAUM, SR .
ANALYTICAL BIOCHEMISTRY, 1982, 126 (01) :131-138
[23]   Design and synthesis of novel β-diketo derivatives as HIV-1 integrase inhibitors [J].
Hu, Liming ;
Zhang, Sulei ;
He, Xianzhuo ;
Luo, Zaigang ;
Wang, Xiaoli ;
Liu, Wei ;
Qin, Xuemei .
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (01) :177-182
[24]   Isatin-pyrazole benzenesulfonamide hybrids potently inhibit tumor-associated carbonic anhydrase isoforms IX and XII [J].
Ibrahim, Hany S. ;
Abou-Seri, Sahar M. ;
Tanc, Muhammet ;
Elaasser, Mahmoud M. ;
Abdel-Aziz, Hatem A. ;
Supuran, Claudiu T. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 103 :583-593
[25]  
Janovska D., 2003, Czech Journal of Food Sciences, V21, P107
[26]   Synthesis and biological evaluation of amino acid-linked 1,2,3-bistriazole conjugates as potential antimicrobial agents [J].
Kaushik, C. P. ;
Lal, Kashmiri ;
Kumar, Ashwani ;
Kumar, Sunil .
MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (06) :2995-3004
[27]   Isocytosine-based inhibitors of xanthine oxidase: Design, synthesis, SAR, PK and in vivo efficacy in rat model of hyperuricemia [J].
Khanna, Smriti ;
Burudkar, Sandeep ;
Bajaj, Komal ;
Shah, Pranay ;
Keche, Ashish ;
Ghosh, Usha ;
Desai, Avani ;
Srivastava, Ankita ;
Kulkarni-Almeida, Asha ;
Deshmukh, Nitin J. ;
Dixit, Amol ;
Brahma, Manoja K. ;
Bahirat, Umakant ;
Doshi, Lalit ;
Nemmani, Kumar V. S. ;
Tannu, Prashant ;
Damre, Anagha ;
B-Rao, Chandrika ;
Sharma, Rajiv ;
Sivaramakrishnan, H. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (24) :7543-7546
[28]   Magnetically separable CuFe2O4 nano particles catalyzed multicomponent synthesis of 1,4-disubstituted 1,2,3-triazoles in tap water using 'click chemistry' [J].
Kumar, B. S. P. Anil ;
Reddy, K. Harsha Vardhan ;
Madhav, B. ;
Ramesh, K. ;
Nageswar, Y. V. D. .
TETRAHEDRON LETTERS, 2012, 53 (34) :4595-4599
[29]   Synthesis, characterization and antimicrobial activity of 4-((1-benzyl/phenyl-1H-1,2,3-triazol-4-yl)methoxy)benzaldehyde analogues [J].
Lal, Kashmiri ;
Yadav, Pinki ;
Kumar, Ashwani .
MEDICINAL CHEMISTRY RESEARCH, 2016, 25 (04) :644-652
[30]   Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings (Reprinted from Advanced Drug Delivery Reviews, vol 23, pg 3-25, 1997) [J].
Lipinski, CA ;
Lombardo, F ;
Dominy, BW ;
Feeney, PJ .
ADVANCED DRUG DELIVERY REVIEWS, 2001, 46 (1-3) :3-26