Synthesis of enterolactone and enterodiol precursors as potential inhibitors of human estrogen synthetase (aromatase)

被引:30
|
作者
Mäkelä, TH [1 ]
Wähälä, KT [1 ]
Hase, TA [1 ]
机构
[1] Univ Helsinki, Dept Chem, Organ Chem Lab, FIN-00014 Helsinki, Finland
关键词
lignan; lactones; Michael reactions; synthesis;
D O I
10.1016/S0039-128X(00)00104-5
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of variably substituted derivatives of lignan lactones and diols were prepared using tandem conjugate addition reaction as a key step. These theoretical precursors of the mammalian lignans enterolactone 1 and enterodiol 3 are moderate or weak inhibitors of human aromatase activity. (C) 2000 Elsevier Science Inc. All rights reserved.
引用
收藏
页码:437 / 441
页数:5
相关论文
共 50 条
  • [1] Enantioselective dehydroxylation of enterodiol and enterolactone precursors by human intestinal bacteria
    Jin, Jong-Sik
    Zhao, Yu-Feng
    Nakamura, Norio
    Akao, Teruaki
    Kakiuchi, Nobuko
    Min, Byung-Sun
    Hattori, Masao
    BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2007, 30 (11) : 2113 - 2119
  • [2] INHIBITION OF HUMAN ESTROGEN SYNTHETASE (AROMATASE) BY FLAVONES
    KELLIS, JT
    VICKERY, LE
    SCIENCE, 1984, 225 (4666) : 1032 - 1034
  • [3] STRUCTURAL CHARACTERIZATION OF THE HUMAN ESTROGEN SYNTHETASE (AROMATASE) GENE
    HARADA, N
    YAMADA, K
    SAITO, K
    KIBE, N
    DOHMAE, S
    TAKAGI, Y
    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1990, 166 (01) : 365 - 372
  • [4] Phytosterols as precursors for the synthesis of aromatase inhibitors: Hemisynthesis of testololactone and testolactone
    Lone, Shabir H.
    Bhat, Khursheed A.
    STEROIDS, 2015, 96 : 164 - 168
  • [5] Design and synthesis of new steroidal inhibitors of estrogen synthase (aromatase)
    Parish, EJ
    Li, SR
    Rao, ZG
    LIPIDS, 2000, 35 (03) : 271 - 277
  • [6] HUMAN-PLACENTA ESTROGEN SYNTHETASE (AROMATASE) PURIFIED BY AFFINITY-CHROMATOGRAPHY
    HAGERMAN, DD
    JOURNAL OF BIOLOGICAL CHEMISTRY, 1987, 262 (05) : 2398 - 2400
  • [8] FURTHER CHARACTERIZATION OF AN ESTROGEN SYNTHETASE (ANDROGEN AROMATASE) SOLUBILIZED FROM HUMAN PLACENTA
    HIGASHIYAMA, T
    OSAWA, Y
    FEDERATION PROCEEDINGS, 1979, 38 (03) : 731 - 731
  • [9] SYNTHESIS OF POTENTIAL INHIBITORS OF THE ENZYME PANTOTHENATE SYNTHETASE
    BAILLIE, AC
    CORNELL, CL
    WRIGHT, BJ
    WRIGHT, K
    TETRAHEDRON LETTERS, 1992, 33 (35) : 5133 - 5136
  • [10] Synthesis of some novel androstanes as potential aromatase inhibitors
    Yadav, Mange Ram
    Sabale, Prafulla M.
    Giridhar, Rajani
    Zimmer, Christina
    Haupenthal, Jorg
    Hartmann, Rolf W.
    STEROIDS, 2011, 76 (05) : 464 - 470