6α-acetoxyandrost-4-ene-3,17-dione | 1816-82-6

• 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: 6α-acetoxyandrost-4-ene-3,17-dione
• 英文别名: 6α-acetoxy-androst-4-ene-3,17-dione；6α-Acetoxy-androst-4-en-3,17-dion；6alpha-Acetoxy-4-androstene-3,17-dione；[(6S,8R,9S,10R,13S,14S)-10,13-dimethyl-3,17-dioxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-6-yl] acetate
• CAS: 1816-82-6
• 化学式: C₂₁H₂₈O₄
• 分子量: 344.451
• InChiKey: WGJULUODXUVWJZ-ZYVPZICASA-N

物化性质

• 熔点：
  174-176 °C
• 沸点：
  479.6±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6α-acetoxyandrost-4-ene-3,17-dione 在 sodium hydride 作用下， 以 xylene 为溶剂， 反应 96.0h， 以50 mg的产率得到5'-methylfuro-(4',3',2',4,5,6)-androst-5-ene-3,17-dione
  参考文献：
  名称：

  Boynton, Juliette; Hansom, James R.; Kiran, Ismail, Journal of Chemical Research, Miniprint, 1999, # 11, p. 2701 - 2716

  摘要：

  DOI：
• 作为产物：
  描述：

  6β-acetoxyandrost-4-ene-3,17-dione 在 氢溴酸 、 溶剂黄146 作用下， 反应 48.0h， 以150 mg的产率得到6α-acetoxyandrost-4-ene-3,17-dione
  参考文献：
  名称：

  Boynton, Juliette; Hansom, James R.; Kiran, Ismail, Journal of Chemical Research, Miniprint, 1999, # 11, p. 2701 - 2716

  摘要：

  DOI：

文献信息

• Investigations on steroids. XX. 6β- and 6α-Acetoxy- and Hrdroxy-Derivatives of Progesterone and Androstenedione
  作者：Charles P. Balant、Maximilian Ehrenstein

  DOI：10.1021/jo50012a005

  日期：1952.12
• Probing the binding pocket of the active site of aromatase with 6-ether or 6-ester substituted androst-4-ene-3,17-diones and their diene and triene analogs
  作者：Mitsuteru Numazawa、Momoko Shelangouski、Mina Nagasaka

  DOI：10.1016/s0039-128x(00)00169-0

  日期：2000.12

  A series of 6-ester- (3 and 4) and 6-ether- (7 and 8) substituted androst-4-ene-3,17-diones (androstenediones) and their 1,4-diene analogs (5 and 6, and 9 and 10) as well as CB-substituted 4,6-diene and 1,4,6-triene steroids 11 and 12 were synthesized as aromatase inhibitors to gain insight into the structure-activity relationship between various substituents and inhibitory activity. All of the inhibitors synthesized blocked aromatase in a competitive manner. The inhibitory activities of all of the steroids, except for the 6 beta -benzoates 4g and 6h and the 6 beta -acetate 6a, were fairly effective to very powerful (K-i: 7.0 -320 nM). The 6 alpha -n-hexanoyloxy- and 6 alpha -benzyloxyandrostenediones (3e and 7e) were the most potent inhibitors (K-i: 7.0 nM each). In the series of 4-ene and 1,4-diene steroids, the 6 alpha -substituted steroids had higher affinity for the enzyme than the corresponding 6 beta -isomers. In the 1,4-diene steroid series, 6 beta -substituted steroids 6a, e, g, and 10a, b, e caused a time-dependent inactivation of aromatase, whereas their 6 alpha -isomers 5 and 9 essentially did not. The ether-substituted 1,4,6-trienes 12 inactivated the enzyme in a time-dependent manner; in contrast, their 4,6-diene analogs 11 did not. The substrate androstenedione blocked the inactivation, but no significant effect of L-cysteine was observed. Based on molecular modeling with the PM3 method, along with the present inhibition and inactivation results, it is thought that both the steric effects of the 6-substituents as well as the electronic effects of the C-6 oxygen functions play a critical role in the binding of inhibitors to the active site of aromatase. (C) 2000 Elsevier Science Inc. All rights reserved.
• INVESTIGATIONS ON STEROIDS. V. ACETOLYSIS OF THE STEREOISOMERIC 5,6-OXIDES AND PREPARATION OF THE ACETATES OF 4-ANDROSTENE-3, 17-DIONE-6(α)-OL AND 6(α)-HYDROXY-11-DESOXYCORTICOSTERONE.¹
  作者：MAXIMILIAN EHRENSTEIN

  DOI：10.1021/jo01204a016

  日期：1941.7