Synthesis of 4-trifluoromethylsteroids:: A novel class of steroid 5α-reductase inhibitors

被引：0
|
作者：
Fei, XS [1 ]
Tian, WS [1 ]
Chen, QY [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Lab Organofluorine Chem, Shanghai 200032, Peoples R China
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1997年 / 7卷 / 24期
关键词：
D O I：
暂无
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A concise synthetic approach to 4-trifluoromethyl steroids, a novel class of steroid 5 alpha-reductase inhibitors, is described. Direct trifluoromethylation of steroid olefinic bromide with methyl fluorosulfonyl-difluoroacetate was used as a key step in the synthesis. The compound 4 exhibited highly inhibitory activity than Finasteride in in vitro assay. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码：3113 / 3118
页数：6
相关论文
共 50 条
  • [31] Simple bi- and tricyclic inhibitors of human steroid 5α-reductase
    Abell, AD
    Prince, MJ
    McNulty, AM
    Neubauer, BL
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (17) : 1909 - 1911
  • [32] Indole and benzimidazole derivatives as steroid 5α-reductase inhibitors in the rat prostate
    Takami, H
    Kishibayashi, N
    Ishii, A
    Kumazawa, T
    BIOORGANIC & MEDICINAL CHEMISTRY, 1998, 6 (12) : 2441 - 2448
  • [33] INHIBITION OF STEROID 5-ALPHA-REDUCTASE BY INVERTED, COMPETITIVE INHIBITORS
    MCDONALD, IA
    NYCE, PL
    MUENCH, DM
    GATES, CA
    BLOHM, TR
    LAUGHLIN, ME
    WEINTRAUB, PM
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (06) : 847 - 851
  • [34] STEROIDAL A-RING ARYL CARBOXYLIC-ACIDS - A NEW CLASS OF STEROID 5-ALPHA-REDUCTASE INHIBITORS
    HOLT, DA
    LEVY, MA
    LADD, DL
    OH, HJ
    ERB, JM
    HEASLIP, JI
    BRANDT, M
    METCALF, BW
    JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (03) : 937 - 942
  • [35] Pyrimido-Pyrimidines: A Novel Class of Dihydrofolate Reductase Inhibitors
    Banjanac, Mihailo
    Tatic, Iva
    Ivezic, Zrinka
    Tomic, Sanja
    Dumic, Jerka
    FOOD TECHNOLOGY AND BIOTECHNOLOGY, 2009, 47 (03) : 236 - 245
  • [36] SORBINIL - A MEMBER OF THE NOVEL CLASS OF SPIROHYDANTOIN ALDOSE REDUCTASE INHIBITORS
    SARGES, R
    PETERSON, MJ
    METABOLISM-CLINICAL AND EXPERIMENTAL, 1986, 35 (04): : 101 - 104
  • [37] Novel pyrroleacetic acids. Selective inhibitors of human type 2 steroid 5 alpha-reductase.
    Seko, T
    Lee, SJ
    Frierson, MR
    Cao, CX
    Miskowski, TA
    Blazewski, KM
    Das, B
    Sircar, JC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 62 - MEDI
  • [38] 3,3-diphenylpentane skeleton as a steroid skeleton substitute:: Novel inhibitors of human 5α-reductase 1
    Hosoda, Shinnosuke
    Hashimoto, Yuichi
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (19) : 5414 - 5418
  • [39] (1-benzylindole-3-yl)alkanoic acids;: Novel nonsteroidal inhibitors of steroid 5α-reductase (I)
    Sawada, K
    Hirai, H
    Golden, P
    Okada, S
    Sawada, Y
    Hashimoto, M
    Tanaka, H
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1998, 46 (11) : 1683 - 1687
  • [40] N-substituted 4-(4-carboxyphenoxy)benzamides.: Synthesis and evaluation as inhibitors of steroid-5α-reductase type 1 and 2
    Picard, F
    Hartmann, RW
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2002, 17 (03) : 187 - 196
12345