Synthetic bicyclic iminosugar derivatives fused thiazolidin-4-one as new potential HIV-RT inhibitors

被引:19
作者
Chen, Hua [1 ]
Yang, Tianyu [1 ]
Wei, Sinan [1 ]
Zhang, Hongzhi [1 ]
Li, Rui [1 ]
Qin, Zhanbin [1 ]
Li, Xiaoliu [1 ]
机构
[1] Hebei Univ, Coll Chem & Environm Sci, Key Lab Chem Biol Hebei Prov, Baoding 071002, Peoples R China
基金
中国国家自然科学基金;
关键词
Bicyclic azasugar; Thiazolidin-4-one; HIV-RT inhibitor; Pummerer rearrangement; PUMMERER REACTION; INDOLIZIDINES;
D O I
10.1016/j.bmcl.2012.09.100
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Novel bicyclic iminosugar derivatives fused thiazolidin-4-one were conveniently synthesized by double Pummerer rearrangements, and their HIV reverse transcriptase (RT) inhibitory activities were preliminary examined. The notable anti-HIV-RT activity demonstrated that such bicyclic azasugars hold potential as a new kind of HIV-RT inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7041 / 7044
页数:4
相关论文
共 34 条
[1]  
[Anonymous], REVERSE TRANSCRIPTAS
[2]  
[Anonymous], 2007, IMINOSUGARS SYNTHESI
[3]   NAGSTATIN, A NEW INHIBITOR OF N-ACETYL-BETA-D-GLUCOSAMINIDASE, PRODUCED BY STREPTOMYCES-AMAKUSAENSIS MG846-FF3 - TAXONOMY, PRODUCTION, ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITIES [J].
AOYAGI, T ;
SUDA, H ;
UOTANI, K ;
KOJIMA, F ;
AOYAMA, T ;
HORIGUCHI, K ;
HAMADA, M ;
TAKEUCHI, T .
JOURNAL OF ANTIBIOTICS, 1992, 45 (09) :1404-1408
[4]  
Asano N., 2008, GLYCOSCIENCE CHEM CH, P1887
[5]   Synthesis of diversely functionalized pyrrolizidines and indolizidines using olefin ring-closing metathesis [J].
Ben-Othman, Raja ;
Othman, Mohamed ;
Ciamala, Kabula ;
Knorr, Michael ;
Strohmann, Carsten ;
Decroix, Bernard .
TETRAHEDRON, 2009, 65 (25) :4846-4854
[6]   Synthesis and evaluation of sulfamide-type indolizidines as glycosidase inhibitors [J].
Benltifa, Mahmoud ;
Moreno, M. Isabel Garcia ;
Mellet, Carmen Ortiz ;
Fernandez, Jose M. Garcia ;
Wadouachi, Anne .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (09) :2805-2808
[7]   Diastereoselective Nitrenium Ion-Mediated Cyclofunctionalization: Total Synthesis of (+)-Castanospermine [J].
Bowen, Edward G. ;
Wardrop, Duncan J. .
ORGANIC LETTERS, 2010, 12 (22) :5330-5333
[8]   The Pummerer reaction: Methodology and strategy for the synthesis of heterocyclic compounds [J].
Bur, SK ;
Padwa, A .
CHEMICAL REVIEWS, 2004, 104 (05) :2401-2432
[9]  
Chen H, 2011, CHINESE J ORG CHEM, V31, P249
[10]   Radical cyclizations of acylsilanes in the synthesis of (+)-swainsonine and formal synthesis of (-)-epiquinamide [J].
Chen, Ming-Jen ;
Tsai, Yeun-Min .
TETRAHEDRON, 2011, 67 (08) :1564-1574