3-methoxy-13β-D-homoestra-1,3,5(10),16-tetraen-17a-one | 59903-45-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3-methoxy-13β-D-homoestra-1,3,5(10),16-tetraen-17a-one
• 英文别名: 3-methoxy-D-homoestra-1,3,5(10),16-tetraene；(4aS,4bR,10bS,12aS)-8-methoxy-12a-methyl-4,4a,4b,5,6,10b,11,12-octahydrochrysen-1-one
• CAS: 59903-45-6
• 化学式: C₂₀H₂₄O₂
• 分子量: 296.409
• InChiKey: WOKRXKYSGQVAQD-XSYGEPLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methoxy-13β-D-homoestra-1,3,5(10),16-tetraen-17a-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、2.0 MPa 条件下， 反应 24.0h， 以92%的产率得到3-methoxy-13β-D-homoestra-1,3,5(10)-trien-17a-one
  参考文献：
  名称：

  Synthesis and receptor-binding examinations of the normal and 13-epi-D-homoestrones and their 3-methyl ethers

  摘要：

  An effective epimerization of the normal estrone 3-methyl and 3-benzyl ethers by using o-phenylenediamine and AcOH made the possibility for facile entry into the 13alpha-estrone series. Combination of this synthetic methodology with an isolation step carried out by means of the Girard-P reagent, the corresponding ethers of 13-epi-estrone were obtained in excellent yields. The 3-hydroxy and 3-methoxy D-homoestrone derivatives in both the normal and the 13alpha-estrone series were then synthesized and tested in vitro in a radioligand-binding assay. The estrogen receptor recognizes these compounds, but their relative binding affinities (RBAs) are lower than that of the reference compound 3,17beta-estradiol. The progesterone receptor-binding affinities of the four D-homo derivatives were also tested showing low values for 13alpha-D-homoestrone and its 3-methyl ether. Pharmacologically, these 13alpha-D-homoestrone derivatives are estrogen receptor-selective molecules. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00181-2
• 作为产物：
  描述：

  (1S,3S,4aS,4bR,10bS,12aS)-3-Iodo-8-methoxy-12a-methyl-1,2,3,4,4a,4b,5,6,10b,11,12,12a-dodecahydro-chrysen-1-ol 在 jones reagent 作用下， 以 丙酮 为溶剂， 以58%的产率得到(3S,4aS,4bR,10bS,12aS)-3-Iodo-8-methoxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydro-2H-chrysen-1-one
  参考文献：
  名称：

  Synthesis of novel halogen-containing d-homoestrone and 13α-d-homoestrone derivatives by Lewis acid-induced intramolecular Prins reaction

  摘要：

  A simple synthetic route has been developed for the synthesis of16-halo-D-homosteroids in both the normal and 13-epiestrone series by the Lewis acid-catalyzed cyclization of an unsaturated secoestrone aldehyde and its 13alpha isomer. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00742-1

文献信息

• Stereoselective Synthesis of New Halogen-containing D-Homoestrone Derivatives
  作者：É. Frank、E. Mernyák、J. Wölfling、Gy. Schneider

  DOI：10.1055/s-2002-20455

  日期：——

  The Lewis acid-induced cyclization of the 3-methyl and 3-benzyl ethers of an unsaturated secoestrone aldehyde furnished D-homosteroids containing 16β-oriented halogens on the sterane skeleton.

  路易斯酸诱导的不饱和癸烯雌酮醛的 3-甲基和 3-苄基醚的环化提供了在甾烷骨架上含有 16β 取向卤素的 D-同型甾体。
• [DE] Delta<15>-D-HOMOSTEROIDE MIT ANDROGENER WIRKUNG<br/>[EN] Delta<15>-D-HOMOSTEROIDS HAVING AN ANDROGENIC EFFECT<br/>[FR] Delta<15>-D-HOMOSTEROIDES A EFFET ANDROGENE
  申请人：SCHERING AG

  公开号：WO2005021573A1

  公开（公告）日：2005-03-10

  Die Erfindung betrifft Δ15-D-Homosteroide der allgemeinen Formel (I). Verfahren zu deren Herstellung und pharmazeutische Zusammensetzungen, die diese Verbindungen enthalten. Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) besitzen androgene Aktivität.

  这个发明涉及一般式（I）的Δ15-D-Homosteroid，其制备方法和包含这些化合物的药物组合物。这些一般式（I）的化合物具有雄激素活性。
• Synthesis and receptor-binding examinations of the normal and 13-epi-D-homoestrones and their 3-methyl ethers
  作者：János Wölfling、Erzsébet Mernyák、Éva Frank、George Falkay、Árpád Márki、Renáta Minorics、Gyula Schneider

  DOI：10.1016/s0039-128x(02)00181-2

  日期：2003.3

  An effective epimerization of the normal estrone 3-methyl and 3-benzyl ethers by using o-phenylenediamine and AcOH made the possibility for facile entry into the 13alpha-estrone series. Combination of this synthetic methodology with an isolation step carried out by means of the Girard-P reagent, the corresponding ethers of 13-epi-estrone were obtained in excellent yields. The 3-hydroxy and 3-methoxy D-homoestrone derivatives in both the normal and the 13alpha-estrone series were then synthesized and tested in vitro in a radioligand-binding assay. The estrogen receptor recognizes these compounds, but their relative binding affinities (RBAs) are lower than that of the reference compound 3,17beta-estradiol. The progesterone receptor-binding affinities of the four D-homo derivatives were also tested showing low values for 13alpha-D-homoestrone and its 3-methyl ether. Pharmacologically, these 13alpha-D-homoestrone derivatives are estrogen receptor-selective molecules. (C) 2002 Elsevier Science Inc. All rights reserved.
• Synthesis of novel halogen-containing d-homoestrone and 13α-d-homoestrone derivatives by Lewis acid-induced intramolecular Prins reaction
  作者：János Wölfling、Éva Frank、Erzsébet Mernyák、Gábor Bunkóczi、Jose A Cvesta Seijo、Gyula Schneider

  DOI：10.1016/s0040-4020(02)00742-1

  日期：2002.8

  A simple synthetic route has been developed for the synthesis of16-halo-D-homosteroids in both the normal and 13-epiestrone series by the Lewis acid-catalyzed cyclization of an unsaturated secoestrone aldehyde and its 13alpha isomer. (C) 2002 Elsevier Science Ltd. All rights reserved.