An efficient microwave assisted synthesis of novel class of Rhodanine derivatives as potential HIV-1 and JS']JSP-1 inhibitors

被引:26
作者
Kamila, Sukanta [1 ]
Ankati, Haribabu [1 ]
Biehl, Edward R. [1 ]
机构
[1] So Methodist Univ, Dept Chem, Dallas, TX 75275 USA
关键词
3-Phenyl-2-thioxothiazolidin-4-one; 2-(1H-Indol-3-yl)-2-oxoacetaldehyde; Acid chloride; HSnBu(3); MW irradiation; AGENTS; INDOLE;
D O I
10.1016/j.tetlet.2011.05.114
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(Z)-5-(2-(1H-Indol-3-yl)-2-oxoethylidene)-3-phenyl-2-thioxothiazolidin-4-one (7a-q) derivatives have been synthesized by the condensation reaction of 3-phenyl-2-thioxothiazolidin-4-ones (3a-h) with suitably substituted 2-(1H-indo1-3-yl)-2-oxoacetaldehyde (6a-d) under microwave condition. The thioxo-thiazolidine-4-ones were prepared from the corresponding aromatic amines (la-e) and di-(carboxy-methyl)-trithiocarbonyl (2). The aldehydes (6a-h) were synthesized from the corresponding acid chlorides (5a-d) using HSnBu(3). (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4375 / 4377
页数:3
相关论文
共 28 条
[1]  
Alvord E, 1934, U.S. Patent, Patent No. 1962109
[2]   Synthesis of 2-Benzylidene and 2-Hetarylmethyl Derivatives of 2H-1,4-Benzoxazin-3-(4H)-ones as Neuroprotecting Agents [J].
Ankati, Haribabu ;
Akubathini, Shashidhar Kumar ;
D'Mello, Santosh R. ;
Biehl, Edward R. .
SYNTHETIC COMMUNICATIONS, 2010, 40 (16) :2364-2376
[3]   Fascaplysin-inspired diindolyls as selective inhibitors of CDK4/cyclin D1 [J].
Aubry, Carine ;
Wilson, A. James ;
Emmerson, Daniel ;
Murphy, Emma ;
Chan, Yu Yam ;
Dickens, Michael P. ;
Garcia, Marcos D. ;
Jenkins, Paul R. ;
Mahale, Sachin ;
Chaudhuri, Bhabatosh .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (16) :6073-6084
[4]   Synthesis and Structure-Activity Relationship Studies of 3-Substituted Indolin-2-ones as Effective Neuroprotective Agents [J].
Balderamos, Michael ;
Ankati, Haribabu ;
Akubathini, Shashidhar Kumar ;
Patel, Anish V. ;
Kamila, Sukanta ;
Mukherjee, Chandrani ;
Wang, Lulu ;
Biehl, Edward R. ;
D'Mello, Santosh R. .
EXPERIMENTAL BIOLOGY AND MEDICINE, 2008, 233 (11) :1395-1402
[5]   SOME 3-SUBSTITUTED RHODANINES [J].
BROWN, FC ;
BRADSHER, CK ;
MORGAN, EC ;
TETENBAUM, M ;
WILDER, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (02) :384-388
[6]   Synthesis and aldose reductase inhibitory activity of 5-arylidene-2,4-thiazolidinediones [J].
Bruno, G ;
Costantino, L ;
Curinga, C ;
Maccari, R ;
Monforte, F ;
Nicolò, F ;
Ottanà, R ;
Vigorita, MG .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (04) :1077-1084
[7]  
BRUTCHER FV, 1958, J ORG CHEM, V23, P146
[8]   Adverse effects of antiretroviral therapy [J].
Carr, A ;
Cooper, DA .
LANCET, 2000, 356 (9239) :1423-1430
[9]  
CIBA A. G., 1946, Swiss Patent, Patent No. 242300
[10]   Rhodanine derivatives as inhibitors of JS']JSP-1 [J].
Cutshall, NS ;
O'Day, C ;
Prezhdo, M .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (14) :3374-3379