Microwave-assisted synthesis of 3'-indolyl substituted 4H-chromenes catalyzed by DMAP and their antimicrobial activity

被引:63
作者
Kathrotiya, Harshad G. [1 ]
Patel, Manish P. [1 ]
机构
[1] Sardar Patel Univ, Dept Chem, Vallabh Vidyanagar 388120, Gujarat, India
关键词
4H-Chromene; Indole; DMAP; Microwave irradiation; MCR; In vitro antimicrobial activity; ONE-POT SYNTHESIS; IN-VITRO; ANTIBACTERIAL ACTIVITY; CHROMENE DERIVATIVES; BIOLOGICAL-ACTIVITY; ANTIOXIDANT; BENZIMIDAZOLES; IRRADIATION; INDOLES; BEARING;
D O I
10.1007/s00044-011-9861-4
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A new series of indole-based chromene derivatives 4a-4p has been synthesized by one pot cyclocondensation reaction of 2-phenyl-1H-indole-3-carbaldehyde 1a-1h; malononitrile 2; and 1,3-cyclohexanedione/dimedone 3a/b under microwave irradiation catalyzed by an organocatalyst 4-(N,N-dimethylamino) pyridine. Easy experimental procedure, high yield, selectivity, and shorter reaction time are the imperative features of this method. All the compounds were screened against a representative panel of bacteria and fungi. Some of the compounds are found to be equipotent or more potent than that of standard drugs as evident from SAR study.
引用
收藏
页码:3406 / 3416
页数:11
相关论文
共 57 条
[21]   A Convenient One-Pot Synthesis of Some New 3-(2-Phenyl-6-(2-thienyl)-4-pyridyl)hydroquinolin-2-ones Under Microwave Irradiation and Their Antimicrobial Activities [J].
Ladani, Niraj K. ;
Patel, Manish P. ;
Patel, Ranjan G. .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2010, 185 (03) :658-662
[22]  
Ladani NK, 2009, INDIAN J CHEM B, V48, P261
[23]   An efficient three component one-pot synthesis of some new octahydroquinazolinone derivatives and investigation of their antimicrobial activities [J].
Ladani, Niraj K. ;
Patel, Manish P. ;
Patel, Ranjan G. .
ARKIVOC, 2009, :292-302
[24]  
Ladani NK, 2011, CHIN CHEM L IN PRESS
[25]   InCl3 mediated one-pot multicomponent synthesis, anti-microbial, antioxidant and anticancer evaluation of 3-pyranyl indole derivatives [J].
Lakshmi, Neelakandan Vidhya ;
Thirumurugan, Prakasam ;
Noorulla, K. M. ;
Perumal, Paramasivan. T. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (17) :5054-5061
[26]   Synthesis and in vitro antimicrobial activity of new 3-(2-morpholinoquinolin-3-yl) substituted acrylonitrile and propanenitrile derivatives [J].
Makawana, Jigar A. ;
Patel, Manish P. ;
Patel, Ranjan G. .
CHEMICAL PAPERS, 2011, 65 (05) :700-706
[27]   Synthesis and in vitro antimicrobial evaluation of penta-substituted pyridine derivatives bearing the quinoline nucleus [J].
Makawana, Jigar A. ;
Patel, Manish P. ;
Patel, Ranjan G. .
MEDICINAL CHEMISTRY RESEARCH, 2012, 21 (05) :616-623
[28]   Synthesis and identification of β-aryloxyquinolines and their pyrano[3,2-c] chromene derivatives as a new class of antimicrobial and antituberculosis agents [J].
Mungra, Divyesh C. ;
Patel, Manish R. ;
Rajani, Dhanji P. ;
Patel, Ranjan G. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (09) :4192-4200
[29]   Microwave-assisted synthesis of some new tetrazolo[1,5-a]quinoline-based benzimidazoles catalyzed by p-TsOH and investigation of their antimicrobial activity [J].
Mungra, Divyesh C. ;
Patel, Manish P. ;
Patel, Ranjan G. .
MEDICINAL CHEMISTRY RESEARCH, 2011, 20 (06) :782-789
[30]   An efficient one-pot synthesis and in vitro antimicrobial activity of new pyridine derivatives bearing the tetrazoloquinoline nucleus [J].
Mungra, Divyesh C. ;
Patel, Manish P. ;
Patel, Ranjan G. .
ARKIVOC, 2009, :64-74