4-chloro-4-androstene-3,17-dione | 16318-49-3

• 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: 4-chloro-4-androstene-3,17-dione
• 英文别名: 4-chloro-androst-4-ene-3,17-dione；4-Chlor-androst-4-en-3,17-dion；4-chloroandrost-4-ene-3,17-dione；(8R,9S,10R,13S,14S)-4-chloro-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 16318-49-3
• 化学式: C₁₉H₂₅ClO₂
• 分子量: 320.859
• InChiKey: MRGZILIKEDFESE-KZQROQTASA-N

物化性质

• 熔点：
  180-182 °C
• 沸点：
  447.0±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-4-androstene-3,17-dione 在 叔丁基二甲基氯硅烷 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 2.0h， 生成 4-chloro-16-(E)-benzylideneandrost-1,4-diene-3,17-dione
  参考文献：
  名称：

  新型4-氯-16E-亚苄基甾体衍生物的合成与表征

  摘要：

  以雄烯二酮为原料，我们合成了 11 种新型 4-chloro-16-(E)-benzlidene androst-1,4-diene-3,17-dione 衍生物。所有最终产品都是新颖的，并通过 1H NMR、13C NMR 和 HRMS 光谱法进行鉴定。

  DOI：

  10.3184/174751917x15094552081198
• 作为产物：
  描述：

  雄烯二酮 在 吡啶 、 乙醚 、 氯 、 丙酸 作用下， 生成 4-chloro-4-androstene-3,17-dione
  参考文献：
  名称：

  Kirk et al., Journal of the Chemical Society, 1956, p. 1184

  摘要：

  DOI：

文献信息

• 20-Fluoro-17(20)-vinyl steroids
  申请人：——

  公开号：US20020019548A1

  公开（公告）日：2002-02-14

  The invention related to 20&xgr;-fluoropregna-4,17(20)-dien-3-on-21-oic acid ethyl ester, 20&xgr;-fluoro-3&bgr;-hydroxypregna-4,17(20)-dien-21-oic acid ethyl ester, 20&xgr;-fluoro-21-hydroxypregna-4,17(20)-dien-3-one, 20&xgr;-fluoropregna-4,17(20)-dien-3&bgr;,21-diol and related compounds and to compositions incorporating these compounds, as well as the inhibition of C 17,20 lyase, 5&agr;-reductase and C 17 -hydroxylase, and to the use of these compounds in the treatment of androgen and estrogen mediated or dependent disorders, including benign prostatic hyperplasia, prostate cancer, breast cancer and DHT-mediated disorders such as acne and hirsutism. Treatment of disorders related to the over synthesis of cortisol, for example, Cushing's Syndrome are also included. The treatment of androgen-dependent disorders also includes a combination therapy with known androgen-receptor antagonists, such as flutamide. The compounds of the invention have the following general formulae: 1

  本发明涉及20&xgr;-氟孕-4,17（20）-二烯-3-酮-21-羧酸乙酯，20&xgr;-氟-3&bgr;-羟基孕-4,17（20）-二烯-21-羧酸乙酯，20&xgr;-氟-21-羟基孕-4,17（20）-二烯-3-酮，20&xgr;-氟孕-4,17（20）-二烯-3&bgr;，21-二醇及其相关化合物，以及包含这些化合物的组合物，以及抑制C17,20裂解酶、5&agr;-还原酶和C17-羟化酶，并将这些化合物用于治疗雄激素和雌激素介导或依赖性疾病，包括良性前列腺增生症、前列腺癌、乳腺癌和DHT介导的疾病，如痤疮和多毛症。本发明还包括治疗与皮质醇过度合成有关的疾病，例如库欣综合征。雄激素依赖性疾病的治疗还包括与已知雄激素受体拮抗剂（如氟他胺）的联合治疗。本发明的化合物具有以下一般式：1
• Aromatase inhibitors. Synthesis and biological activity of androstenedione derivatives
  作者：David A. Marsh、Harry J. Brodie、Wesley Garrett、Chon Hwa Tsai-Morris、Angela M. H. Brodie

  DOI：10.1021/jm00383a017

  日期：1985.6

  The synthesis and biological evaluation of androstenedione derivatives as inhibitors of estrogen biosynthesis are described. The results show that 4-hydroxy analogues are among the most potent in vitro inhibitors of the series. Esterification of the 4-hydroxy steroids generally reduced activity. Further conjugation of the 3-keto 4-ene system to give 4-hydroxy-4,6-androstadiene-3,17-dione caused more rapid inactivation of aromatase in rat ovarian microsomes than 4-hydroxyandrostenedione. Some compounds exhibited differences in activity when tested for inhibition of human placental microsomes vs. rat ovarian microsomes. The 4-hydroxyandrostenedione derivatives and their nonbulky esters were generally more potent in vitro and in vivo inhibitors than other substituted steroids in the series. Several of the synthesized compounds markedly reduce (50-81%) estrogen levels in rats on proestrus and/or had antifertility action. To date, none of the compounds surpassed the in vivo inhibitory action of 4-hydroxy-4-androstene-3,17-dione or its 4-acetate derivative.
• Bourban, Caroline Y. M.; Hanson, James R.; Hitchcock, Peter B., Journal of Chemical Research, Miniprint, 1990, # 9, p. 2050 - 2066
  作者：Bourban, Caroline Y. M.、Hanson, James R.、Hitchcock, Peter B.

  DOI：——

  日期：——
• Dmochowska-Gladysz,J.; Siewinski,A., Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1977, vol. 25, p. 581 - 587
  作者：Dmochowska-Gladysz,J.、Siewinski,A.

  DOI：——

  日期：——
• Process for the preparation of 4-amino-androstenedione derivatives
  申请人：FARMITALIA CARLO ERBA S.r.l.

  公开号：EP0291290B1

  公开（公告）日：1992-01-22