Solid-phase combinatorial synthesis of 5-arylalkylidene rhodanine

被引:46
作者
Lee, CL [1 ]
Sim, MM [1 ]
机构
[1] Inst Mol & Cell Biol, Singapore 117609, Singapore
关键词
solid-phase synthesis; rhodanine; aldehydes; ketones; condensation;
D O I
10.1016/S0040-4039(00)00866-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rhodanine-3-acetic acid was loaded on Wang resin or Rink amide resin. Alternatively, the thiocarbonyl-diimidazole-activated Wang amino acid resin or 2-chlorotrityl resin was reacted with methyl thioglycolate to yield the rhodanine moieties. It was then condensed at the C-5 active methylene with either aromatic aldehydes or aromatic ketones. 5-Arylalkylidene rhodanine was obtained upon resin cleavage. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5729 / 5732
页数:4
相关论文
共 10 条
[1]   4-THIAZOLIDINONES [J].
BROWN, FC .
CHEMICAL REVIEWS, 1961, 61 (05) :463-521
[2]   Comprehensive survey of combinatorial library synthesis: 1998 [J].
Dolle, RE ;
Nelson, KH .
JOURNAL OF COMBINATORIAL CHEMISTRY, 1999, 1 (04) :235-282
[3]   N-GLUCOPYRANOSYL-5-ARALKYLIDENERHODANINES - SYNTHESIS AND ANTIBACTERIAL AND ANTI-VIRAL ACTIVITIES [J].
FOYE, WO ;
TOVIVICH, P .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1977, 66 (11) :1607-1611
[4]   Novel indole containing thiazolidinedione derivatives as potent euglycemic and hypolipidaemic agents [J].
Lohray, BB ;
Bhushan, V ;
Rao, PB ;
Madhavan, GR ;
Murali, N ;
Rao, KN ;
Reddy, KA ;
Rajesh, BM ;
Reddy, PG ;
Chakrabarti, R ;
Rajagopalan, R .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (07) :785-788
[5]  
MOMOSE Y, 1991, Chemical and Pharmaceutical Bulletin (Tokyo), V39, P1440
[6]   An efficient high-speed synthetic route to amino-substituted thiazolidinone libraries [J].
Munson, MC ;
Cook, AW ;
Josey, JA ;
Rao, C .
TETRAHEDRON LETTERS, 1998, 39 (40) :7223-7226
[7]  
OHISHI Y, 1990, CHEM PHARM BULL, V38, P1911
[8]  
Peet N P, 2000, IDrugs, V3, P131
[9]   Novel hepatitis C virus protease inhibitors: Thiazolidine derivatives [J].
Sudo, K ;
Matsumoto, Y ;
Matsushima, M ;
Fujiwara, M ;
Konno, K ;
Shimotohno, K ;
Shigeta, S ;
Yokota, T .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1997, 238 (02) :643-647
[10]   THE SYNTHESIS OF 2,3-DISUBSTITUTED-4-THIAZOLIDONES [J].
TROUTMAN, HD ;
LONG, LM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (10) :3436-3439