16α,17α-cyclohexane-5α-pregnene-3,20-dione | 123247-48-3

• 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: 16α,17α-cyclohexane-5α-pregnene-3,20-dione
• 英文别名: 5α(H)-16α,17α-cyclohexano-4,5-dihydroprogesterone；16α,17α-cyclohexano-5α-pregnane-3,20-dione；16α,17α-cyclohexano-5α-dihydroprogesterone；(4aS,4bS,6aS,6bS,10aR,11aS,11bR,13aS)-6b-acetyl-4a,6a-dimethyl-3,4,4b,5,6,7,8,9,10,10a,11,11a,11b,12,13,13a-hexadecahydro-1H-indeno[2,1-a]phenanthren-2-one
• CAS: 123247-48-3
• 化学式: C₂₅H₃₈O₂
• 分子量: 370.576
• InChiKey: LIMAIPVNZLVWQK-QRSGIJRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  16α,17α-cyclohexane-5α-pregnene-3,20-dione 在 pyridinium hydrobromide perbromide 、 calcium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 溶剂黄146 为溶剂， 反应 0.83h， 生成 16α,17α-cyclohexane-5α-pregn-1-ene-3,20-dione
  参考文献：
  名称：

  Biological activity of transformed steroids

  摘要：

  DOI：

  10.1007/bf00771697
• 作为产物：
  描述：

  (16beta,17alpha)-17-乙酰基-16,24-环-21-去甲胆-4-烯-3-酮 在 jones reagent 、 氨 、 lithium 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 0.27h， 生成 16α,17α-cyclohexane-5α-pregnene-3,20-dione
  参考文献：
  名称：

  Some derivatives of pregna-D6?-pentaranes as possible antagonists of progesterone

  摘要：

  Some derivatives of progestins of the pregna-D-6'-pentarane series have been obtained and examined for their possible hormonal and antihormonal activity in the Clauberg-McPhail assay as well as in the pregnancy maintenance test in ovariectomized rabbits. 16 alpha, 17 alpha-Cyclohexanoprogesterones of the 19-methyl and 19-nor series (1-4) saturated in ring A, which are inactive as progestins, exhibited a remarkable antiprogesterone effect. They decreased the McPhail index under combined administration with progesterone in a dose-dependable manner and completely inhibited the action of the latter in the pregnancy maintenance test.

  DOI：

  10.1007/bf00702407

文献信息

• In vivo study on biotransformation of pentacyclic analogs of progesterone: Identification of their metabolites by HPLC-MS method
  作者：Inna S. Levina、Andrey K. Nazarov、Georgy V. Nazarov、Lidia E. Kulikova、Yury V. Kuznetsov、Andrey S. Dmitrenok、Dmitry V. Minin、Aleksey V. Aksenov、Igor V. Zavarzin

  DOI：10.1016/j.jsbmb.2019.105436

  日期：2019.11

  Progesterone derivatives containing the D' additional cyclohexane ring in the 16α,17α-positions of steroid core (pregna-D′-pentaranes) exhibited high in vitro and in vivo selective progestogenic activity. The assessment of their biotransformation in the body, and the identification of possible metabolites are integral parts of a potential drug studies. Here we describe the results of in vivo metabolic

  在类固醇核心的16α，17α位（孕烷-D'-戊烷）中含有D'附加环己烷环的孕酮衍生物表现出很高的体外和体内选择性孕激素活性。评估它们在体内的生物转化以及鉴定可能的代谢物是潜在药物研究不可或缺的部分。在这里，我们描述了6α-甲基-16α，17α-环己酮-4-烯-3,20-二酮1及其6-脱甲基类似物2体内代谢转化的结果及其在大鼠尿液中的代谢产物鉴定。我们合成并充分表征（1D和2D NMR，HRMS）11种可能的代谢物作为标准品。然后，我们开发了LC-MS / MS分析方法，包括样品制备和色谱条件，用于鉴定检测到的1和2的代谢物。 5α-和5β-3,20-二酮-，3β-羟基-20-酮5α-，3-酮20（S）-羟基-5α-，3β，20（S）-二羟基-5α-代谢物在大鼠尿液样本中发现了化合物1和2的混合物。在所检查的生物尿液样本中未检测到起始类固醇1和2以及3β，20（R）-二羟基代谢物。因此，我们
• Biological activity of transformed steroids
  作者：A. V. Kamernitskii、I. S. Levina、L. E. Kulikova、G. V. Nikitina、V. V. Korkhov

  DOI：10.1007/bf00771697

  日期：1990.3
• Some derivatives of pregna-D6?-pentaranes as possible antagonists of progesterone
  作者：I. S. Levina、G. V. Nikitina、L. E. Kulikova、A. V. Kamernitzky

  DOI：10.1007/bf00702407

  日期：1995.3

  Some derivatives of progestins of the pregna-D-6'-pentarane series have been obtained and examined for their possible hormonal and antihormonal activity in the Clauberg-McPhail assay as well as in the pregnancy maintenance test in ovariectomized rabbits. 16 alpha, 17 alpha-Cyclohexanoprogesterones of the 19-methyl and 19-nor series (1-4) saturated in ring A, which are inactive as progestins, exhibited a remarkable antiprogesterone effect. They decreased the McPhail index under combined administration with progesterone in a dose-dependable manner and completely inhibited the action of the latter in the pregnancy maintenance test.