20ξ-cyano-20ξ-hydroxy-4-pregnen-3-one | 62653-60-5

• 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: 20ξ-cyano-20ξ-hydroxy-4-pregnen-3-one
• 英文别名: 20-hydroxy-3-oxo-23,24-dinor-20ξH-chol-4-ene-21-nitrile；20-Hydroxy-3-oxo-23,24-dinor-20ξH-chol-4-en-21-nitril；20-Carbonitril-20-hydroxypregn-4-en-3-on；20-Cyano-20-hydroxy-4-pregnene-3-one；2-[(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-hydroxypropanenitrile
• CAS: 62653-60-5
• 化学式: C₂₂H₃₁NO₂
• 分子量: 341.494
• InChiKey: FZUDLGOZOWJAJT-WHPCQORBSA-N

物化性质

• 熔点：
  202-206 °C
• 沸点：
  518.2±23.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  20ξ-cyano-20ξ-hydroxy-4-pregnen-3-one 在 吡啶 、 氢氧化钾 、 乙醚 、 碘 、 sodium ethanolate 、 对甲苯磺酸 、 溶剂黄146 、 苯 作用下， 生成 醋酸去氧皮质酮
  参考文献：
  名称：

  Ercoli; de Ruggieri, Gazzetta Chimica Italiana, 1954, vol. 84, p. 312,321

  摘要：

  DOI：
• 作为产物：
  描述：

  黄体酮 、 丙酮氰醇 生成 20ξ-cyano-20ξ-hydroxy-4-pregnen-3-one
  参考文献：
  名称：

  Ercoli; de Ruggieri, Gazzetta Chimica Italiana, 1954, vol. 84, p. 312,321

  摘要：

  DOI：

文献信息

• 20-substituted pregnene derivatives and their use as androgen synthesis
  申请人：Research Corporation Technologies, Inc.

  公开号：US05264427A1

  公开（公告）日：1993-11-23

  Novel 20-substituted-pregnene derivatives, compositions containing such derivatives and methods for their use and manufacture are disclosed. The 20-substituted-pregnene derivatives inhibit the androgen biosynthesis enzymes 17(alpha)-hydroxylase/C.sub.17,20 -lyase and 5(alpha)-reducatase and are therefore useful for reducing or inhibiting production of androgens where they have an adverse role in a disease or physiological condition in vertebrate species.

  本发明公开了一种20-取代孕烯衍生物，包含这种衍生物的组合物以及使用和制造这些衍生物的方法。这些20-取代孕烯衍生物抑制雄激素生物合成酶17（α）-羟化酶/C.sub.17,20-裂解酶和5（α）-还原酶，因此在脊椎动物物种中，当雄激素在疾病或生理状况中起到不利作用时，这些衍生物是有用的，可以减少或抑制雄激素的产生。
• Synthesis and Evaluation of Pregnane Derivatives as Inhibitors of Human Testicular 17α-Hydroxylase/C_17,20-Lyase^,
  作者：Ji-song Li、Yan Li、Chong Son、Angela M. H. Brodie

  DOI：10.1021/jm960245f

  日期：1996.1.1

  The pregnene derivatives with modifications at the 17,20-side chain and D-ring were synthesized and evaluated as inhibitors of human testicular 17 alpha-hydroxylase/C-17,C-20-lyase. The results demonstrate that compounds which have 20-substituents with moderate to strong dipole properties, such as 20-oxime (3, 20), 20 beta-ol (24, 30), and 20 beta-carboxaldehyde (27), are potent inhibitors of this enzyme complex. The 20-substituents with hydrophobic property were devoid of inhibitory activity, e.g., the dimethylhydrazones 8 and 9. The 16-ene together with 20-oxime (20) showed the most potent inhibition of this enzyme complex, whereas 17(20)-ene modification as in 17(20)-ene-20-carbonitrile (14) did not increase activity in comparison to the 20 beta-carbonitrile (16). The bioisostere of 27 with 20-aza (19) also reduced the inhibitory activity. The results showed that isomeric configurations at the 20-position of some steroidal compounds are important factors which influence the potency of the inhibition significantly (e.g., 20 beta-ols 24 and 30 were 3-5-fold more potent than 20 alpha-ols 23 and 29). As expected, some compounds based on the pregn-5-en-3 beta-ol skeleton, which is similar to the natural substrate of human testicular 17 alpha-hydroxylase/C-17,C-20-lyase in A- and B-rings, showed more potent inhibition than similar compounds which are based on the pregn-4-en-3-one skeleton (e.g., 23-25 compared to 29-31). These results suggest that A- and B-rings make significant contributions to the binding of these steroidal compounds to the 17 alpha-hydroxylase and C-17,C-20-lyase. In comparison to ketoconazole, a nonsteroidal inhibitor of 17 alpha-hydroxylase and C-17,C-20-lyase which has been used in the treatment of prostatic cancer, the steroidal compounds 20, 24, and 27 demonstrate more potent inhibition for this enzyme complex. These inhibitors warrant further investigation in biological systems. The structural features of these compounds may serve as leads in the design of new inhibitors.
• Photolysis of .alpha.-peracetoxynitriles. 2. A comparison of two synthetic approaches to 18-cyano-20-ketosteroids
  作者：Robert W. Freerksen、W. Edward Pabst、Michael L. Raggio、Steven A. Sherman、Randall R. Wroble、David S. Watt

  DOI：10.1021/ja00447a041

  日期：1977.3
• Kalvoda,J. et al., Helvetica Chimica Acta, 1966, vol. 49, p. 424 - 436
  作者：Kalvoda,J. et al.

  DOI：——

  日期：——
• Steroid cyanohydrins
  申请人：UPJOHN CO

  公开号：US02655517A1

  公开（公告）日：1953-10-13