An operational transformation of 3-carboxy-4-quinolones into 3-nitro-4-quinolones via ipso-nitration using polysaccharide supported copper nanoparticles: synthesis of 3-tetrazolyl bioisosteres of 3-carboxy-4-quinolones as antibacterial agents

被引:15
作者
Azad, Chandra S. [1 ]
Narula, Anudeep K. [1 ]
机构
[1] GGS Indraprastha Univ, Hygeia Ctr Excellence Pharmaceut Sci CEPS, Sec 16C, New Delhi, India
关键词
IMMOBILIZED PALLADIUM NANOPARTICLES; RECYCLABLE HETEROGENEOUS CATALYST; SUBSTRATE PNP-SSS; EFFICIENT; CHITOSAN; SILICA; WATER; HECK; 3-NITROQUINOLINES; (E)-NITROOLEFINS;
D O I
10.1039/c5ra26909a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chitosan supported Cu nano-particles have been synthesized, and utilized for the synthesis of 3-nitro-4-quinolones from 3-carboxy-4-quinolones via ipso nitration. The synthesized 3-nitro derivatives of 4-quinolones were successfully converted into their 3-tetrazolyl bioisosteres which showed increased antibacterial activity as compared to the standard ciprofloxacin.
引用
收藏
页码:19052 / 19059
页数:8
相关论文
共 66 条
[1]   Green Chemistry: Principles and Practice [J].
Anastas, Paul ;
Eghbali, Nicolas .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :301-312
[2]  
Asahina Y, 1992, Prog Drug Res, V38, P57
[3]   Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis [J].
Astruc, D ;
Lu, F ;
Aranzaes, JR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) :7852-7872
[4]  
Azad C. S., 2015, RSC ADV, V5, P100223
[5]   Stereoconvergent synthesis of 1-deoxynojirimycin isomers by using the 3 component 4 centred Ugi reaction [J].
Azad, Chandra S. ;
Saxena, Anil K. .
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (06) :665-669
[6]   Operative conversions of 3-carboxy-4-quinolones into 3-nitro-4-quinolones via ipso-nitration: potential antifilarial agents as inhibitors of Brugia malayi thymidylate kinase [J].
Azad, Chandra S. ;
Balaramnavar, Vishal M. ;
Khan, Imran A. ;
Doharey, Pawan K. ;
Saxena, Jitendra K. ;
Saxena, Anil K. .
RSC ADVANCES, 2015, 5 (100) :82208-82214
[7]   Novel Glycoconjugate of 8-Fluoro Norfloxacin Derivatives as Gentamicin-resistant Staphylococcus aureus Inhibitors: Synthesis and Molecular Modelling Studies [J].
Azad, Chandra S. ;
Bhunia, Shome S. ;
Krishna, Atul ;
Shukla, Praveen K. ;
Saxena, Anil K. .
CHEMICAL BIOLOGY & DRUG DESIGN, 2015, 86 (04) :440-446
[8]   One pot conversion of carbohydrates alcohol into chloride via benzotriazole sulfonate [J].
Azad, Chandra S. ;
Saxena, Anil K. .
TETRAHEDRON, 2013, 69 (12) :2608-2612
[9]   Natural Indian Natrolite zeolite-supported Cu nanoparticles: a new and reusable heterogeneous catalyst for N-arylation of sulfonamides with boronic acids in water under ligand-free conditions [J].
Azarifar, Davood ;
Soleimanei, Fatemeh .
RSC ADVANCES, 2014, 4 (24) :12119-12126
[10]   Magnetically retrievable catalysts for asymmetric synthesis [J].
Baig, R. B. Nasir ;
Nadagouda, Mallikarjuna N. ;
Varma, Rajender S. .
COORDINATION CHEMISTRY REVIEWS, 2015, 287 :137-156