3-methoxy-13α-estra-1,3,5(10)-triene-17α-ol | 4896-45-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3-methoxy-13α-estra-1,3,5(10)-triene-17α-ol
• 英文别名: 3-methoxy-13α-estra-1,3,5(10)-trien-17α-ol；(8R,9S,13R,14S,17R)-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-ol
• CAS: 4896-45-1
• 化学式: C₁₉H₂₆O₂
• 分子量: 286.414
• InChiKey: ULAADVBNYHGIBP-UJWQCDCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

ADMET

代谢

(13alpha)-3-甲氧基-雌甾-1,3,5(10)-三烯-17alpha-醇已知的人类代谢物包括雌二醇。

(13alpha)-3-methoxy-estra-1,3,5(10)-triene-17alpha-ol has known human metabolites that include Estradiol.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  3-甲氧基雌酮 在 sodium tetrahydroborate 、 溶剂黄146 、 邻苯二胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 3-methoxy-13α-estra-1,3,5(10)-triene-17α-ol
  参考文献：
  名称：

  Conformational Design for 13α-Steroids

  摘要：

  The diastereomeric 16-bromo- and 16-azido-17-alcohols 5-8, 11, 12, 16, and 17 and 17-ketones 3, 4, 9, and 10 of the 13 alpha-estra-1,3,5(10)-triene series were synthesized as precursors for biologically active compounds and chiral Ligands for metal complexation. Conformational investigations of these and some other compounds via X-ray analysis and H-1 NMR spectroscopy show the existence of compounds with the classical steroid conformation (ring C chair, restricted conformation of ring D) and such with an atypical ring C twist-boat and a flexible ring D conformation. It could be shown that 17 beta-substituents or flattening of the D-ring are responsible for the twist-boat conformation, whereas compounds containing a 17 alpha-substituent or 17 keto group possess the classical conformation. By varying the substituents, compounds with either of these conformations can be intentionally synthesized. MO calculations confirmed the relative stability of the twist-boat conformation.

  DOI：

  10.1021/jo000108x

文献信息

• Addition reactions at the 16(17) double bond of 3-methoxy-13$alpha;-estra-1,3,5(10),16-tetraene*1
  作者：E MERNYAK

  DOI：10.1016/s0039-128x(02)00177-0

  日期：2003.3

  3-methoxy-13alpha-estra-1,3,5(10),16-tetraene 1 with diborane, catecholborane, and 9-BBN were investigated in order to determine the stereochemical outcome and to synthesize new 13alpha-estra-1,3,5(10)-trienes for biological and conformational investigations. It was shown that the sterically demanding reagent 9-BBN participated in a preferred beta attack (53% 16betaOH 10, 34% 17betaOH 8, 13% 16alphaOH

  研究了环氧化，次溴酸的添加以及3-甲氧基-13alpha-estra-1,3,5（10），16-丁烯1与乙硼烷，儿茶酚硼烷和9-BBN的硼氢化反应，以确定其立体化学结果并合成新的13alpha-estra-1,3,5（10）-三烯用于生物学和构象研究。已经表明，空间上需要的试剂9-BBN参与了优选的β攻击（53％的16betaOH 10、34％的17betaOH 8、13％的16alphaOH 11）。该立体化学结果与另一个顺式加成反应的结果，即最近描述的1的OsO4二羟基化[Steroids 68（2003）113]一致。使用较小的试剂，例如B2H6，儿茶酚硼烷或单过氧邻苯二甲酸镁，观察到的立体选择性降低，而β攻击仅略有过量。次溴酸的离子反式加成反应产生了两种具有16beta，17alpha（4，76％）和16alpha，17beta构型（5，24％）的17-溴16-醇，通过16,17a
• Synthesis and biological evaluation of 13α-estrone derivatives as potential antiproliferative agents
  作者：Johanna Szabó、Zoltán Pataki、János Wölfling、Gyula Schneider、Noémi Bózsity、Renáta Minorics、István Zupkó、Erzsébet Mernyák

  DOI：10.1016/j.steroids.2016.05.010

  日期：2016.9

  13 alpha-Estrone derivatives containing various substituents on C-3 and C-17 were synthesized, and evaluated by means of MU assays for in vitro antiproliferative activity against a panel of human adherent cancer cell lines (HeLa, MCF-7, A2780 and A431). Compounds with N-benzyltriazolylmethoxy moieties on C-3 proved to be more potent than their 3-hydroxy or 3-ether counterparts. Some triazoles exerted substantial cytostatic effects against particular tumor cell lines, with submicromolar IC50 values. (C) 2016 Elsevier Inc. All rights reserved.
• Nambara,T. et al., Chemical and pharmaceutical bulletin, 1969, vol. 17, # 11, p. 2366 - 2370
  作者：Nambara,T. et al.

  DOI：——

  日期：——
• Conformational Design for 13α-Steroids
  作者：Bruno Schönecker、Corinna Lange、Manuela Kötteritzsch、Wolfgang Günther、Jennie Weston、Ernst Anders、Helmar Görls

  DOI：10.1021/jo000108x

  日期：2000.9.1

  The diastereomeric 16-bromo- and 16-azido-17-alcohols 5-8, 11, 12, 16, and 17 and 17-ketones 3, 4, 9, and 10 of the 13 alpha-estra-1,3,5(10)-triene series were synthesized as precursors for biologically active compounds and chiral Ligands for metal complexation. Conformational investigations of these and some other compounds via X-ray analysis and H-1 NMR spectroscopy show the existence of compounds with the classical steroid conformation (ring C chair, restricted conformation of ring D) and such with an atypical ring C twist-boat and a flexible ring D conformation. It could be shown that 17 beta-substituents or flattening of the D-ring are responsible for the twist-boat conformation, whereas compounds containing a 17 alpha-substituent or 17 keto group possess the classical conformation. By varying the substituents, compounds with either of these conformations can be intentionally synthesized. MO calculations confirmed the relative stability of the twist-boat conformation.