Synthesis of new enantiopure thiepane derivatives and their evaluation as glycosidase inhibitors

被引:10
作者
Arcelli, A
Cerè, V
Peri, F
Pollicino, S
Ricci, A
机构
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
[2] Univ Bologna, Dept Organ Chem, I-40136 Bologna, Italy
关键词
D O I
10.1016/S0957-4166(02)00087-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Starting from inexpensive alcohol sugars we have synthesised a series of oxygen- and nitrogen-containing enantiopure thiepanes to investigate the structural and stereochemical requirements for inhibitory activity against a variety of glycosidases. An interesting trend was observed on analysis of the biological screening results for these derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:191 / 196
页数:6
相关论文
共 21 条
[1]   Synthesis and glycosidase inhibition of new enantiopure 2,3-diamino conduritols [J].
Arcelli, A ;
Cerè, V ;
Peri, F ;
Pollicino, S ;
Ricci, A .
TETRAHEDRON, 2001, 57 (16) :3439-3444
[2]   Synthesis and biological activity of the (-)-(2R,3S,4S)-3-azido-4-methoxy-2-(1′S-methoxy-2′-azido)ethyl-thiolane [J].
Arcelli, A ;
Cerè, V ;
Peri, F ;
Pollicino, S ;
Sabatino, P .
TETRAHEDRON-ASYMMETRY, 2000, 11 (06) :1389-1395
[3]   REVISED STANDARD VALUES FOR PH MEASUREMENTS FROM 0 TO 95 DEGREES C [J].
BATES, RG .
JOURNAL OF RESEARCH OF THE NATIONAL BUREAU OF STANDARDS SECTION A-PHYSICS AND CHEMISTRY, 1962, 66 (02) :179-+
[4]  
*BIOS, 1993, FIG P WIND VERS 2XX
[5]   THIOSUGARS FROM D-MANNITOL [J].
FUZIER, M ;
LEMERRER, Y ;
DEPEZAY, JC .
TETRAHEDRON LETTERS, 1995, 36 (36) :6443-6446
[6]   INTERFERENCE WITH HIV-INDUCED SYNCYTIUM FORMATION AND VIRAL INFECTIVITY BY INHIBITORS OF TRIMMING GLUCOSIDASE [J].
GRUTERS, RA ;
NEEFJES, JJ ;
TERSMETTE, M ;
DEGOEDE, REY ;
TULP, A ;
HUISMAN, HG ;
MIEDEMA, F ;
PLOEGH, HL .
NATURE, 1987, 330 (6143) :74-77
[7]  
HODGSON J, 1991, BIO-TECHNOL, V9, P609
[8]   New series of potent, orally bioavailable, non-peptidic cyclic sulfones as HIV-1 protease inhibitors [J].
Kim, CU ;
McGee, LR ;
Krawczyk, SH ;
Harwood, E ;
Harada, Y ;
Swaminathan, S ;
Bischofberger, N ;
Chen, MS ;
Cherrington, JM ;
Xiong, SF ;
Griffin, L ;
Cundy, KC ;
Lee, A ;
Yu, B ;
Gulnik, S ;
Erickson, JW .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (18) :3431-3434
[9]   SYNTHESIS OF 1,6-THIOANHYDRO-D-GLUCITOL [J].
KUSZMANN, J ;
SOHAR, P .
CARBOHYDRATE RESEARCH, 1976, 48 (01) :23-32
[10]   1,6-ANHYDRO-1(6)-THIO-L-IDITOL AND D-MANNITOL, AND SOME DERIVATIVES THEREOF [J].
KUSZMANN, J ;
SOHAR, P .
CARBOHYDRATE RESEARCH, 1977, 56 (01) :105-115