Synthesis and biological activity of β-fluoroalkyl β-amino alcohols

被引:38
作者
Bravo, P
Crucianelli, M
Ono, T
Zanda, M
机构
[1] Politecn Milan, Dipartimento Chim, I-20131 Milan, Italy
[2] CNR, Ctr Studio Sostanze Organ Nat, I-20131 Milan, Italy
[3] Natl Ind Res Inst Nagoya, Kita Ku, Nagoya, Aichi 4628510, Japan
基金
日本科学技术振兴机构;
关键词
fluoroalkyl; amino alcohols; florfenicol; synthesis; bioactivity; chiral;
D O I
10.1016/S0022-1139(99)00024-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
This paper reviews the synthesis of unnatural chiral beta-fluoroalkyl beta-amino alcohols, with an emphasis on their biological activity and pharmaceutical applications. (C) 1999 Elsevier Science S.A, All rights reserved.
引用
收藏
页码:27 / 49
页数:23
相关论文
共 86 条
[1]   Diastereoselective synthesis of the nonracemic methyl syn-(3-fluoroalkyl)isoserinates [J].
Abouabdellah, A ;
Begue, JP ;
BonnetDelpon, D ;
Nga, TTT .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25) :8826-8833
[2]  
Abouabdellah A, 1996, SYNLETT, P399
[3]   REACTION OF HYDROFLUORIC-ACID WITH AZIRINES - SYNTHESIS OF ALPHA-FLUOROKETONES AND DIFLUOROAMINES - STUDY OF REACTION APPLICATIONS [J].
ALVERNHE, G ;
LACOMBE, S ;
LAURENT, A .
TETRAHEDRON LETTERS, 1980, 21 (15) :1437-1440
[4]  
ALVERNHE G, 1983, J CHEM RES-S, P246
[5]   Two isosteric fluorinated derivatives of the powerful glucosidase inhibitors, 1-deoxynojirimycin and 2,5-dideoxy-2,5-imino-D-mannitol: Syntheses and glycosidase-inhibitory activities of 1,2,5-trideoxy-2-fluoro-1,5-imino-D-glucitol and of 1,2,5-trideoxy-1-fluoro-2,5-imino-D-mannitol [J].
Andersen, SM ;
Ebner, M ;
Ekhart, CW ;
Gradnig, G ;
Legler, G ;
Lundt, I ;
Stutz, AE ;
Withers, SG ;
Wrodnigg, T .
CARBOHYDRATE RESEARCH, 1997, 301 (3-4) :155-166
[6]   New versatile fluorinated chiral building blocks: Synthesis and reactivity of optically pure alpha-(fluoroalkyl)-beta-sulfinylenamines [J].
Arnone, A ;
Bravo, P ;
Capelli, S ;
Fronza, G ;
Meille, SV ;
Zanda, M ;
Cavicchio, G ;
Crucianelli, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3375-3387
[7]   New versatile fluorinated chiral building blocks: Synthesis and reactivity of optically pure alpha-(fluoroalkyl)-beta-sulfinylenamines (vol 61, pg 3383, 1996) [J].
Arnone, A ;
Bravo, P ;
Capelli, S ;
Fronza, G ;
Meille, SV ;
Zanda, M ;
Cavicchio, G ;
Crucianelli, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9635-9635
[8]   UNUSUAL NONOXIDATIVE PUMMERER REARRANGEMENT OF GAMMA-TRIFLUORO-BETA-AMINOSULFOXIDES [J].
ARNONE, A ;
BRAVE, P ;
BRUCHE, L ;
CRUCIANELLI, M ;
VICHI, L ;
ZANDA, M .
TETRAHEDRON LETTERS, 1995, 36 (40) :7301-7304
[9]   ISOPENICILLIN-N SYNTHASE - A NEW MODE OF REACTIVITY [J].
BALDWIN, JE ;
LYNCH, GP ;
SCHOFIELD, CJ .
TETRAHEDRON, 1992, 48 (41) :9085-9100
[10]   ALDOL AND MICHAEL ADDITIONS OF FLUORINATED NITROALKANES TO ALDEHYDES, KETONES, AND ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].
BECK, AK ;
SEEBACH, D .
CHEMISCHE BERICHTE-RECUEIL, 1991, 124 (12) :2897-2911