Sulfamic acid: an efficient and recyclable solid acid catalyst for the synthesis of 4,5-dihydropyrrolo[1,2-a]quinoxalines

被引:27
作者
Kamal, Ahmed [1 ]
Babu, Korrapati Suresh [1 ]
Hussaini, S. M. Ali [1 ]
Srikanth, P. S. [1 ]
Balakrishna, Moku [1 ]
Alarifi, Abdullah [2 ]
机构
[1] Indian Inst Chem Technol, CSIR, Med Chem & Pharmacol, Hyderabad 500007, Andhra Pradesh, India
[2] King Saud Univ, Coll Sci, Dept Chem, Catalyt Chem Res Chair, Riyadh 11451, Saudi Arabia
关键词
Dihydropyrrolo[1,2-a]quinoxalines; Sulfamic acid; Reusability; Cytotoxicity; ONE-POT SYNTHESIS; BIOLOGICAL EVALUATION; RECEPTOR ANTAGONISTS; ANTICANCER AGENTS; MOLECULAR DOCKING; DERIVATIVES; INHIBITORS; QUINOXALINES; APOPTOSIS; BINDING;
D O I
10.1016/j.tetlet.2015.06.006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, efficient, and eco-friendly method has been developed for the synthesis of 4,5-dihydropyrrolo[1,2-a]quinoxalines using sulfamic acid (H2NSO3H, SA), a green and recyclable catalyst in water. The method employs readily available catalysts and is notable for short reaction time, operational simplicity, and high yields. The catalyst can be recovered and reused without loss of activity and more importantly, the reaction uses water as a solvent which is naturally abundant and environmentally benign. Moreover, the synthesized compounds were screened for their cytotoxic potential against two human cancer cell lines. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4619 / 4622
页数:4
相关论文
共 38 条
[1]  
Alleca Sergio, 2003, Farmaco (Lausanne), V58, P639
[2]  
Ameta K.L., 2014, Green Chemistry: Synthesis of Bioactive Heterocycles
[3]   Ionic liquid-regulated sulfamic acid:: chemoselective catalyst for the transesterification of β-ketoesters [J].
Bo, W ;
Ming, YL ;
Shuan, SJ .
TETRAHEDRON LETTERS, 2003, 44 (27) :5037-5039
[4]   NOVEL COMPOUNDS POSSESSING POTENT CAMP AND CGMP PHOSPHODIESTERASE INHIBITORY ACTIVITY - SYNTHESIS AND CARDIOVASCULAR EFFECTS OF A SERIES OF IMIDAZO[1,2-A]QUINOXALINONES AND IMIDAZO[1,5-A]QUINOXALINONES AND THEIR AZA ANALOGS [J].
DAVEY, DD ;
ERHARDT, PW ;
CANTOR, EH ;
GREENBERG, SS ;
INGEBRETSEN, WR ;
WIGGINS, J .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (09) :2671-2677
[5]  
Desplat V, 2008, J ENZYM INHIB MED CH, V23, P648, DOI [10.1080/14756360802205448, 10.1080/14756360802205448 ]
[6]   Sulfamic Acid Catalyzed One-Pot Synthesis of Polyhydroquinolines via the Hantzsch Four Component Condensation Reaction [J].
Foroughifar, Naser ;
Mobinikhaledi, Akbar ;
Fard, Mohammad Ali Bodaghi ;
Moghanian, Hassan ;
Ebrahimi, Sattar .
SYNTHESIS AND REACTIVITY IN INORGANIC METAL-ORGANIC AND NANO-METAL CHEMISTRY, 2009, 39 (03) :161-164
[7]   Arylguanidine and arylbiguanide binding at 5-HT3 serotonin receptors:: A QSAR study [J].
Glennon, RA ;
Daoud, MK ;
Dukat, M ;
Teitler, M ;
Herrick-Davis, K ;
Purohit, A ;
Syed, H .
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (20) :4449-4454
[8]   Synthesis of new pyrrolo[1,2-a]quinoxalines:: potential non-peptide glucagon receptor antagonists [J].
Guillon, J ;
Dallemagne, P ;
Pfeiffer, B ;
Renard, P ;
Manechez, D ;
Kervran, A ;
Rault, S .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1998, 33 (04) :293-308
[9]   Two alternatives for the synthesis of pyrrolo[1,2-a] quinoxaline derivatives [J].
Harrak, Y. ;
Weber, S. ;
Gomez, A. B. ;
Rosell, G. ;
Pujol, M. D. .
ARKIVOC, 2007, :251-259
[10]   Transcriptional profiling of MCF7 breast cancer cells in response to 5-fluorouracil:: Relationship with cell cycle changes and apoptosis, and identification of novel targets of p53 [J].
Hernandez-Vargas, Hector ;
Ballestar, Esteban ;
Carmona-Saez, Pedro ;
von Kobbe, Cayetano ;
Banon-Rodriguez, Inmaculada ;
Esteller, Manel ;
Moreno-Bueno, Gema ;
Palacios, Jose .
INTERNATIONAL JOURNAL OF CANCER, 2006, 119 (05) :1164-1175