6beta-(羟基甲基)雄甾-1,4-二烯-3,17-二酮 | 121021-51-0

• 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
• 中文名称: 6beta-(羟基甲基)雄甾-1,4-二烯-3,17-二酮
• 中文别名: 6β-羟甲基雄烷-1,4-二烯-3,17-二酮；依西美坦相关物质B
• 英文名称: 6β-hydroxymethylandrosta-1,4-diene-3,17-dione
• 英文别名: 6β-Hydroxymethylandrosta-1,4-dien-3,17-dion；6β-hydroxymethyl-1,4-androstadiene-3,17-dione；6beta-Hydroxymethylandrosta-1,4-diene-3,17-dione；(6R,8R,9S,10R,13S,14S)-6-(hydroxymethyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 121021-51-0
• 化学式: C₂₀H₂₆O₃
• 分子量: 314.425
• InChiKey: DAXJNUBSBFUTRP-JKNDIDBPSA-N

物化性质

• 沸点：
  492.0±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6beta-(羟基甲基)雄甾-1,4-二烯-3,17-二酮 在 吡啶 、 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以13%的产率得到6α-Chlormethylandrosta-1,4-dien-3,17-dion
  参考文献：
  名称：

  Goelitzer; Bonnekessel; Jones, Pharmazie, 2006, vol. 61, # 7, p. 575 - 581

  摘要：

  DOI：
• 作为产物：
  描述：

  雄甾-1,4-二烯-3,17-二酮 以 乙醇 、 水 、 苯 为溶剂， 反应 25.0h， 生成 6beta-(羟基甲基)雄甾-1,4-二烯-3,17-二酮
  参考文献：
  名称：

  Goelitzer; Bonnekessel; Jones, Pharmazie, 2006, vol. 61, # 7, p. 575 - 581

  摘要：

  DOI：

文献信息

• Synthesis and aromatase inhibition by potential metabolites of exemestane (6-methylenandrosta-1,4-diene-3,17-dione)
  作者：Franco Buzzetti、Enrico Di Salle、Antonio Longo、Gabriella Briatico

  DOI：10.1016/0039-128x(93)90029-m

  日期：1993.11

  Exemestane (6-methylenandrosta-1,4-diene-3,17-dione; FCE 24304) is an orally active irreversible aromatase inhibitor which is in phase II clinical evaluation for the potential therapy of postmenopausal breast cancer. A series of exemestane analogs, with modifications at the 6-methylene group and with additional reduction at the 17-keto group, were synthesized as potential metabolites and tested in vitro for their effect on human placental aromatase. All these new analogs were found to be less potent in inhibiting aromatase than exemestane. The most effective compound was the 17beta-hydroxy-derivative (compound 2), which is 2.6-fold less potent than exemestane [50% inhibitory concentration (IC50) 69 and 27 nM, respectively]. The various C-6 modified derivatives of the 17-oxo series were found to inhibit the aromatase enzyme in the following descending order: 6-methylene (exemestane) > 6-spirooxirane (6) > 6beta-hydroxymethyl (11) > 6-hydroxymethyl (7) > 6beta-carboxy (13), showing IC50 values of 27, 206, 295, 2,300, and 7,200 nM, respectively. The 17beta-hydroxy analogs of some of the above mentioned compounds were also synthesized (3, 4, 12) and found to be 3-8-fold less potent than the corresponding 17-keto analogs.
• WO2008/32131
  申请人：——

  公开号：——

  公开（公告）日：——
• EXEMESTANE AND ITS INTERMEDIATES AND METHODS OF MAKING THE SAME
  申请人：Cedarburg Pharmaceuticals, Inc.

  公开号：EP1709062B9

  公开（公告）日：2013-02-13
• PROCESS FOR PREPARING AROMATASE INHIBITORS
  申请人：ScinoPharm Taiwan Ltd.

  公开号：EP2142561B9

  公开（公告）日：2014-02-19
• PROCESS FOR THE SELECTIVE ISOLATION, PURIFICATION AND SEPARATION OF MONOHYDROXYLATED 3,17-DIKETO-STEROID COMPOUNDS
  申请人：Richter Gedeon Nyrt.

  公开号：EP2069382B1

  公开（公告）日：2011-03-23