19-(acetylthio)androst-4-ene-3,17-dione | 90212-29-6

• 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: 19-(acetylthio)androst-4-ene-3,17-dione
• 英文别名: S-[[(8S,9S,10S,13S,14S)-13-methyl-3,17-dioxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-10-yl]methyl] ethanethioate
• CAS: 90212-29-6
• 化学式: C₂₁H₂₈O₃S
• 分子量: 360.518
• InChiKey: ODLCBLAUGRDJHC-OAGDOXAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  51.21
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  乙二醇 、 19-(acetylthio)androst-4-ene-3,17-dione 在 对甲苯磺酸一水合物 作用下， 以 苯 为溶剂， 反应 4.0h， 以69%的产率得到3,17-diethylenedioxy-19-acetylthioandrost-5-ene
  参考文献：
  名称：

  6β,19-Bridged androstenedione analogs as aromatase inhibitors

  摘要：

  Inhibition of aromatase is an efficient approach for the prevention and treatment of breast cancer. New 6 beta,19-bridged steroid analogs of androstenedione, 6 beta,19-epithio- and 6 beta,19-methano compounds 11 and 17, were synthesized starting from 19-hydroxyand rostenedione (6) and 19-formylandrost-5-ene-3 beta,17 beta-yl diacetate (12), respectively, as aromatase inhibitors. All of the compounds including known steroids 6 beta,19-epoxyandrostenedione (4) and 6 beta,19-cycloandrostenedione (5) tested were weak to poor competitive inhibitors of aromatase and, among them, 6 beta,19-epoxy steroid 4 provided only moderate inhibition (K-i: 2.2 mu M). These results show that the 6 beta,19-bridged groups of the inhibitors interfere with binding in active site of aromatase. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.06.001
• 作为产物：
  描述：

  19-triflylandrost-4-ene-3,17-dione 在 potassium thioacetate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以558 mg的产率得到19-(acetylthio)androst-4-ene-3,17-dione
  参考文献：
  名称：

  6β,19-Bridged androstenedione analogs as aromatase inhibitors

  摘要：

  Inhibition of aromatase is an efficient approach for the prevention and treatment of breast cancer. New 6 beta,19-bridged steroid analogs of androstenedione, 6 beta,19-epithio- and 6 beta,19-methano compounds 11 and 17, were synthesized starting from 19-hydroxyand rostenedione (6) and 19-formylandrost-5-ene-3 beta,17 beta-yl diacetate (12), respectively, as aromatase inhibitors. All of the compounds including known steroids 6 beta,19-epoxyandrostenedione (4) and 6 beta,19-cycloandrostenedione (5) tested were weak to poor competitive inhibitors of aromatase and, among them, 6 beta,19-epoxy steroid 4 provided only moderate inhibition (K-i: 2.2 mu M). These results show that the 6 beta,19-bridged groups of the inhibitors interfere with binding in active site of aromatase. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.06.001

文献信息

• Interactions of thiol-containing androgens with human placental aromatase
  作者：Patrick J. Bednarski、Sidney D. Nelson

  DOI：10.1021/jm00121a037

  日期：1989.1

  androstenedione. The inhibitory activity of 19-SHA may be explained by two independent mechanisms: (1) suicide inactivation of aromatase in the ferrous state; and (2) a direct "hyper-type II" binding to the remaining portion of the cytochrome in the ferric state. A free thiol group was necessary for the suicide inhibitory activity of 19-SHA; time-dependent inactivation of aromatase by 19-(acetylthio)androst-4-ene-3

  合成并研究了一系列硫醇雄激素，以表征对抑制芳香化酶重要的结构特征。雄烯二酮与2个α-，10个β-或19个位置的硫醇基团的类似物引起人类胎盘芳香化酶的时间依赖性抑制。当将它们的KI和kcat值与4-羟基雄烷-4-烯-3,17-二酮（4-OHa）和10β-炔丙基4-烯-3,17-二酮（PED）的KI和kcat值进行比较时，硫醇雄激素10β-巯基雌二醇-4-烯-3,17-二酮（10β-SHnorA）被证明是最有效的自杀底物。然而，19-巯基和4-烯-3-烯-3,17-二酮（19-SHA）是最好的全能抑制剂。除19-SHA以外的所有化合物均具有正常的I P-450差异光谱以及部分纯化/增溶的人胎盘芳香酶。该系列化合物的Ks值与时间和浓度依赖性抑制实验确定的KI值进行了定性比较。19-SHA诱导了Soret在380和474 nm处的分裂峰，这表明19-硫醇盐直接结合到芳香化酶的三价铁上。这种结合可以
• 6β,19-Bridged androstenedione analogs as aromatase inhibitors
  作者：Sachiko Komatsu、Ayaka Yaguchi、Kouwa Yamashita、Masao Nagaoka、Mitsuteru Numazawa

  DOI：10.1016/j.steroids.2009.06.001

  日期：2009.11

  Inhibition of aromatase is an efficient approach for the prevention and treatment of breast cancer. New 6 beta,19-bridged steroid analogs of androstenedione, 6 beta,19-epithio- and 6 beta,19-methano compounds 11 and 17, were synthesized starting from 19-hydroxyand rostenedione (6) and 19-formylandrost-5-ene-3 beta,17 beta-yl diacetate (12), respectively, as aromatase inhibitors. All of the compounds including known steroids 6 beta,19-epoxyandrostenedione (4) and 6 beta,19-cycloandrostenedione (5) tested were weak to poor competitive inhibitors of aromatase and, among them, 6 beta,19-epoxy steroid 4 provided only moderate inhibition (K-i: 2.2 mu M). These results show that the 6 beta,19-bridged groups of the inhibitors interfere with binding in active site of aromatase. (C) 2009 Elsevier Inc. All rights reserved.