TETRAZOLES OF MANNO-FURANOSES AND RHAMNO-FURANOSES

被引：46
作者：
DAVIS, B
BRANDSTETTER, TW
SMITH, C
HACKETT, L
WINCHESTER, BG
FLEET, GWJ
机构：
[1] OXFORD CTR MOLEC SCI,DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND
[2] GLAXO WELLCOME MED RES CTR,STEVENAGE SG1 2NY,HERTS,ENGLAND
[3] UNIV LONDON,INST CHILD DEV,LONDON WC1 1EH,ENGLAND
[4] UNIV LONDON,GREAT ORMOND ST HOSP CHILDREN,NHS TRUST,LONDON WC1 1EH,ENGLAND
来源：
TETRAHEDRON LETTERS | 1995年 / 36卷 / 41期
关键词：
D O I：
10.1016/0040-4039(95)01518-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of tetrazoles derived from D-mannofuranose and both enantiomers of rhamnofuranose provides the first examples of tetrazole analogues of carbohydrates in the furanose form. The D-furanotetrazoles are potential mannosidase inhibitors whereas the L-rhamnotetrazole may interfere with the biosynthesis of cell walls of mycobacteria and provide a strategy for the treatment of tuberculosis and leprosy.
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收藏
页码：7507 / 7510
页数：4
相关论文
共 12 条
[1]   NITROGEN-IN-THE-RING PYRANOSES AND FURANOSES - STRUCTURAL BASIS OF INHIBITION OF MAMMALIAN GLYCOSIDASES [J].
ASANO, N ;
OSEKI, K ;
KIZU, H ;
MATSUI, K .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (22) :3701-3706
[2]  
ASANO N, 1995, IN PRESS J MED CHEM, V38
[3]   TETRAZOLES OF MANNO-PYRANOSES AND RHAMNO-PYRANOSES - INHIBITION OF GLYCOSIDASES BY TETRAZOLES AND OTHER MANNOSE MIMICS [J].
BRANDSTETTER, TW ;
DAVIS, B ;
HYETT, D ;
SMITH, C ;
HACKETT, L ;
WINCHESTER, BG ;
FLEET, GWJ .
TETRAHEDRON LETTERS, 1995, 36 (41) :7511-7514
[4]   SYNTHESIS OF THE MANNOSIDASE INHIBITORS SWAINSONINE AND 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL AND OF THE RING CONTRACTED SWAINSONINES, (1S, 2R, 7R, 7AR)-1,2,7-TRIHYDROXYPYRROLIZIDINE AND (1S, 2R, 7S, 7AR)-1,2,7-TRIHYDROXYPYRROLIZIDINE [J].
CARPENTER, NM ;
FLEET, GWJ ;
DIBELLO, IC ;
WINCHESTER, B ;
FELLOWS, LE ;
NASH, RJ .
TETRAHEDRON LETTERS, 1989, 30 (51) :7261-7264
[5]  
DESRA GS, 1995, BIOCHEMISTRY-US, V34, P4257
[6]   CONFIGURATIONALLY SELECTIVE TRANSITION-STATE ANALOG INHIBITORS OF GLYCOSIDASES - A STUDY WITH NOJIRITETRAZOLES, A NEW CLASS OF GLYCOSIDASE INHIBITORS [J].
ERMERT, P ;
VASELLA, A ;
WEBER, M ;
RUPITZ, K ;
WITHERS, SG .
CARBOHYDRATE RESEARCH, 1993, 250 (01) :113-128
[7]   SYNTHESIS OF A GLUCOSE-DERIVED TETRAZOLE AS A NEW BETA-GLUCOSIDASE INHIBITOR - A NEW SYNTHESIS OF 1-DEOXYNOJIRIMYCIN [J].
ERMERT, P ;
VASELLA, A .
HELVETICA CHIMICA ACTA, 1991, 74 (08) :2043-2053
[8]   DESIGN SYNTHESIS AND PRELIMINARY EVALUATION OF A POTENT ALPHA-MANNOSIDASE INHIBITOR - 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL [J].
FLEET, GWJ ;
SMITH, PW ;
EVANS, SV ;
FELLOWS, LE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (18) :1240-1241
[9]   STRUCTURE, FUNCTION AND BIOGENESIS OF THE CELL-ENVELOPE OF MYCOBACTERIA IN RELATION TO BACTERIAL PHYSIOLOGY, PATHOGENESIS AND DRUG-RESISTANCE - SOME THOUGHTS AND POSSIBILITIES ARISING FROM RECENT STRUCTURAL INFORMATION [J].
MCNEIL, MR ;
BRENNAN, PJ .
RESEARCH IN MICROBIOLOGY, 1991, 142 (04) :451-463
[10]   INHIBITION OF ALPHA-MANNOSIDASES BY 7 CARBON SUGARS - SYNTHESIS OF SOME 7 CARBON ANALOGS OF MANNOFURANOSE [J].
MYERSCOUGH, PM ;
FAIRBANKS, AJ ;
JONES, AH ;
BRUCE, I ;
CHOI, SMS ;
FLEET, GWJ ;
ALDAHER, SS ;
DIBELLO, IC ;
WINCHESTER, B .
TETRAHEDRON, 1992, 48 (46) :10177-10190
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