21-bromo-3β-acetoxy-17α-hydroxy-5-pregnen-20-one | 93605-12-0

• 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: 21-bromo-3β-acetoxy-17α-hydroxy-5-pregnen-20-one
• 英文别名: [(3S,8R,9S,10R,13S,14S,17R)-17-(2-bromoacetyl)-17-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 93605-12-0
• 化学式: C₂₃H₃₃BrO₄
• 分子量: 453.417
• InChiKey: LJWQTQHQSMSARL-ZGIWMXSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  21-bromo-3β-acetoxy-17α-hydroxy-5-pregnen-20-one 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 0.17h， 以99%的产率得到3β-acetoxy-17α,21-dihydroxy-5-pregnen-20-one
  参考文献：
  名称：

  New preparation and controlled alkaline hydrolysis of 21-bromo-20-oxopregnenes. A facile synthesis of deoxycorticoids

  摘要：

  DOI：

  10.1021/jo00201a016
• 作为产物：
  描述：

  3-beta,17-alpha-二羟基孕甾-5-烯-20-酮 3-乙酸酯 在 copper(ll) bromide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以45%的产率得到21-bromo-3β-acetoxy-17α-hydroxy-5-pregnen-20-one
  参考文献：
  名称：

  New preparation and controlled alkaline hydrolysis of 21-bromo-20-oxopregnenes. A facile synthesis of deoxycorticoids

  摘要：

  DOI：

  10.1021/jo00201a016

文献信息

• Inhibition of steroid C17(20) lyase with C-17-heteroaryl steroids
  作者：Joseph P. Burkhart、Cynthia A. Gates、Marie E. Laughlin、Robert J. Resvick、Norton P. Peet

  DOI：10.1016/0968-0896(96)00135-6

  日期：1996.9

  Steroids bearing a heteroaromatic substituent at C-17 were designed as inhibitors of C-17(20) lyase. The thiazoles, furans, and thiophenes appended to the steroid nucleus were positioned on the alpha-face and the beta-face of the steroid, and conjugated with a 16,17-olefin, to test their ability to coordinate the heme iron of the P450 enzyme complex. The position of the heterocycle with respect to the steroid skeleton was determined to be important for optimum affinity and, in general, compounds with the heterocycle attached to a trigonal center at C-17, had the best affinity for C-17(20) lyase. Simple molecular models were used to compare the three types of heterocyclic-substituted steroids. Copyright (C) 1996 Elsevier Science Ltd