androst-5,9(11)-dien-3,17-dione-3,17-di-ethylene ketal | 149884-29-7

• 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: androst-5,9(11)-dien-3,17-dione-3,17-di-ethylene ketal
• 英文别名: 3,3:17,17-bis(ethylenedioxy)androst-5,9(11)-diene；3,3;17,17-bis-ethanediyldioxy-androsta-5,9(11)-diene；3,3;17,17-Bis-aethandiyldioxy-androsta-5,9(11)-dien
• CAS: 149884-29-7
• 化学式: C₂₃H₃₂O₄
• 分子量: 372.505
• InChiKey: IRRFXNRTVJGCRO-HZEGPAAWSA-N

物化性质

• 沸点：
  504.9±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  androst-5,9(11)-dien-3,17-dione-3,17-di-ethylene ketal 在 溶剂黄146 作用下， 以70%的产率得到雄甾-4,9(11)-二烯-3,17-二酮
  参考文献：
  名称：

  Synthesis of 11-substituted androstenediones and testosterones as human decidual cell growth inhibitors

  摘要：

  11 alpha-Hydroxytestosterone (1a), 11 beta-hydroxytestosterone (1b), 11 alpha-methoxytestosterone (1c), 11 beta-methoxytestosterone (1d), 11-ketotestosterone (1e), and Delta(9(11))-testosterone (1f) were synthesized from hydrocortisone (4b) or 11-epi-hydrocortisone (4a). The six target compounds, together with 11 alpha-methoxyandrostenedione (2c), 11 beta-methoxyandrostenedione, (2d) and their lead compound, testosterone (1), were found to effectively inhibit the growth and differentiation of human decidual cells in culture. There is no observable binding of these compounds to estrogen receptor of rabbit uterus. The introduction of apolar group (e.g., hydroxyl and carbonyl) to C-11 of androstenes decreases both the relative binding affinities to progesterone receptor and the inhibitory effects on human decidual cell growth, while the methylation of 11-hydroxyl group minimizes these effects. The similar effects of a polar group at C-11 of testosterone (1) on the inhibitory effects on human decidual cell growth and the relative binding affinities to progesterone receptor of rabbit uterus may suggest that one of the mechanisms of human decidual cell growth inhibition by these compounds is the anti-progestational activity of these androgens.

  DOI：

  10.1016/0039-128x(94)90027-2
• 作为产物：
  描述：

  氢化可的松 在 manganese(IV) oxide 、 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 苯 为溶剂， 反应 8.0h， 生成 androst-5,9(11)-dien-3,17-dione-3,17-di-ethylene ketal
  参考文献：
  名称：

  Synthesis of 11-substituted androstenediones and testosterones as human decidual cell growth inhibitors

  摘要：

  11 alpha-Hydroxytestosterone (1a), 11 beta-hydroxytestosterone (1b), 11 alpha-methoxytestosterone (1c), 11 beta-methoxytestosterone (1d), 11-ketotestosterone (1e), and Delta(9(11))-testosterone (1f) were synthesized from hydrocortisone (4b) or 11-epi-hydrocortisone (4a). The six target compounds, together with 11 alpha-methoxyandrostenedione (2c), 11 beta-methoxyandrostenedione, (2d) and their lead compound, testosterone (1), were found to effectively inhibit the growth and differentiation of human decidual cells in culture. There is no observable binding of these compounds to estrogen receptor of rabbit uterus. The introduction of apolar group (e.g., hydroxyl and carbonyl) to C-11 of androstenes decreases both the relative binding affinities to progesterone receptor and the inhibitory effects on human decidual cell growth, while the methylation of 11-hydroxyl group minimizes these effects. The similar effects of a polar group at C-11 of testosterone (1) on the inhibitory effects on human decidual cell growth and the relative binding affinities to progesterone receptor of rabbit uterus may suggest that one of the mechanisms of human decidual cell growth inhibition by these compounds is the anti-progestational activity of these androgens.

  DOI：

  10.1016/0039-128x(94)90027-2

文献信息

• A Convenient Syntheses of 9(11)-Dehydrosteroids from 11<i>β</i>-Hydroxysteroids
  作者：Qinjian Zhao、Zhensu Li

  DOI：10.1080/00397919308011239

  日期：1993.5

  11beta-Hydroxy androstenedione was unexpectedly dehydrated during the ketalization of its 3,17-diones. This dehydration reaction can be exploited as a convenient method for the syntheses of 9(11)-dehydrosteroids.
• STEROIDAL CYCLIC KETALS. VII.¹ TRANSFORMATION PRODUCTS OF ADRENOSTERONE. Δ^{4, 9(11)} ANDROSTADIENE-3, 17-DIONE
  作者：SEYMOUR BERNSTEIN、ROBERT H. LENHARD、JAMES H. WILLIAMS

  DOI：10.1021/jo01366a008

  日期：1954.1
• Synthesis of 11-substituted androstenediones and testosterones as human decidual cell growth inhibitors
  作者：Qinjian Zhao、Zhensu Li

  DOI：10.1016/0039-128x(94)90027-2

  日期：1994.3

  11 alpha-Hydroxytestosterone (1a), 11 beta-hydroxytestosterone (1b), 11 alpha-methoxytestosterone (1c), 11 beta-methoxytestosterone (1d), 11-ketotestosterone (1e), and Delta(9(11))-testosterone (1f) were synthesized from hydrocortisone (4b) or 11-epi-hydrocortisone (4a). The six target compounds, together with 11 alpha-methoxyandrostenedione (2c), 11 beta-methoxyandrostenedione, (2d) and their lead compound, testosterone (1), were found to effectively inhibit the growth and differentiation of human decidual cells in culture. There is no observable binding of these compounds to estrogen receptor of rabbit uterus. The introduction of apolar group (e.g., hydroxyl and carbonyl) to C-11 of androstenes decreases both the relative binding affinities to progesterone receptor and the inhibitory effects on human decidual cell growth, while the methylation of 11-hydroxyl group minimizes these effects. The similar effects of a polar group at C-11 of testosterone (1) on the inhibitory effects on human decidual cell growth and the relative binding affinities to progesterone receptor of rabbit uterus may suggest that one of the mechanisms of human decidual cell growth inhibition by these compounds is the anti-progestational activity of these androgens.