3β-acetoxy-21-diazopregn-5-en-20-one | 73792-86-6

• 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: 3β-acetoxy-21-diazopregn-5-en-20-one
• 英文别名: 3β-acetoxy-21-diazo-pregnen-(5)-one-(20)；3β-Acetoxy-21-diazo-pregnen-(5)-on-(20)；[(3S,8S,9S,10R,13S,14S,17S)-17-(2-diazoacetyl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 73792-86-6
• 化学式: C₂₃H₃₂N₂O₃
• 分子量: 384.519
• InChiKey: VZJASVVRXMLTSG-MTMZYOSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  45.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-21-diazopregn-5-en-20-one 在 溴 作用下， 生成 3β-hydroxy-20-oxo-pregnen-(5)-al-(21)
  参考文献：
  名称：

  DE739085

  摘要：

  公开号：
• 作为产物：
  描述：

  3β-acetoxyetienic acid 在 草酰氯 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 3.17h， 生成 3β-acetoxy-21-diazopregn-5-en-20-one
  参考文献：
  名称：

  New steroidal oxazolines, benzoxazoles and benzimidazoles related to abiraterone and galeterone

  摘要：

  Seven new oxazoline, benzoxazole and benzimidazole derivatives were synthesized from 3 beta-acetoxyandrosta-5,16-dien-17-carboxylic, 3 beta-acetoxyandrost-5-en-17 beta-carboxylic and 3 beta-acetoxypregn-5-en-21-oic acids. Docking to active site of human 17 alpha-hydroxylase/17,20-lyase revealed that all oxazolines, as well as benzoxazoles and benzimidazoles comprising Delta(16) could form stable complexes with enzyme, in which steroid moiety is positioned similarly to that of abiraterone and galeterone, and nitrogen atom coordinates heme iron, while 16,17-saturated benzoxazoles and benzimidazoles could only bind in a position where heterocycle is located nearly parallel to heme plane. Modeling of the interaction of new benzoxazole and benzimidazole derivatives with androgen receptor revealed the destabilization of helix 12, constituting activation function 2 (AF2) site, by mentioned compounds, similar to one induced by known antagonist galeterone. The synthesized compounds inhibited growth of prostate carcinoma LNCaP and PC-3 cells at 96 h incubation; the potency of 2'-(3-hydroxyandrosta-5,16-dien-17-yl)-4',5'-dihydro-1',3'-oxazole and 2'-(3 beta-hydroxyandrosta-5,16-dien-17-yl)-benzimidazole was superior and could inspire further investigations of these compounds as potential anti-cancer agents.

  DOI：

  10.1016/j.steroids.2019.108534

文献信息

• Plattner; Heusser, Helvetica Chimica Acta, 1945, vol. 28, p. 1044,1049
  作者：Plattner、Heusser

  DOI：——

  日期：——
• Über Bestandteile der Nebennierenrinde und verwandte Stoffe. 35. Mitteilung. Phosphorsäure- und p-Toluolsulfonsäure-ester des Desoxy-corticosterons und verwandter Stoffe
  作者：T. Reichstein、W. Schindler

  DOI：10.1002/hlca.19400230186

  日期：——
• Desoxy-cortico-steron (21-Oxy-progesteron) aus ?5-3-Oxy-�tio-cholens�ure
  作者：M. Steiger、T. Reichstein

  DOI：10.1002/hlca.193702001158

  日期：——
• Schering A. G., BIOS Final Rep. Nr. 449 <1944> 242
  作者：Schering A. G.

  DOI：——

  日期：——
• DE739085
  申请人：——

  公开号：——

  公开（公告）日：——