(6a,16b,17a)-17-乙酰基-6-甲基-16,24-环-21-去甲胆-4-烯-3-酮 | 58212-84-3

• 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
• 中文名称: (6a,16b,17a)-17-乙酰基-6-甲基-16,24-环-21-去甲胆-4-烯-3-酮
• 英文名称: 6α-methyl-16α,17α-cyclohexanoprogesterone
• 英文别名: Pentarane B；[3H]-Pentarane B；Mecigestone；(4aR,4bS,6aS,6bS,10aR,11aS,11bR,13S)-6b-acetyl-4a,6a,13-trimethyl-4,4b,5,6,7,8,9,10,10a,11,11a,11b,12,13-tetradecahydro-3H-indeno[2,1-a]phenanthren-2-one
• CAS: 58212-84-3
• 化学式: C₂₆H₃₈O₂
• 分子量: 382.587
• InChiKey: OAICPORQJIVREU-SGCXAXHESA-N

物化性质

• 沸点：
  502.7±50.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  (6a,16b,17a)-17-乙酰基-6-甲基-16,24-环-21-去甲胆-4-烯-3-酮 在 5%-palladium/activated carbon 、 氢溴酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以390 mg的产率得到6α-methyl-16α,17α-cyclohexano-5β-pregnane-3,20-dione
  参考文献：
  名称：

  孕酮五环类似物的生物转化体内研究：通过HPLC-MS方法鉴定其代谢物

  摘要：

  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

  DOI：

  10.1016/j.jsbmb.2019.105436
• 作为产物：
  描述：

  (16beta,17alpha)-17-乙酰基-16,24-环-21-去甲胆-4-烯-3-酮 在 palladium on activated charcoal 、 sodium acetate 、 环己烯 、 三氯氧磷 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 28.75h， 生成 (6a,16b,17a)-17-乙酰基-6-甲基-16,24-环-21-去甲胆-4-烯-3-酮
  参考文献：
  名称：

  Synthesis of 6α-methyl-16α, 17α-cyclohexanoprogesteronevia γ-methylenation of 16α, 17α-cyclohexanopregn-4-ene-3,20-dione

  摘要：

  6-Methylene-16 alpha,17 alpha-cyclohexanopregn-4-ene-3,20-dione 2 has been synthesized by the reaction of Delta(4)-3-ketone 1 with CH2(OEt)(2) and POCl3 in the presence of AcONa in 55% yield. Reduction of the product 2 in the presence of 5% Pd/C gives 6 alpha-methyl-16 alpha,17 alpha-cyclohexanoprogesterone 3 in a yield exceeding 70%.

  DOI：

  10.1007/bf02496229

文献信息

• Synthesis of [3H]-cycloalkanoprogesterones (pregna-d'-pentaranes) and study of their interaction with a progesterone receptor
  作者：A. V. Kamernitsky、I. S. Levina、L. E. Kulikova、T. N. Galakhova、V. P. Shevchenko、I. Yu. Nagaev、N. F. Myasoedov、A. N. Smirnov、E. V. Pokrovskaya、T. A. Schelkunova

  DOI：10.1007/bf02505688

  日期：1997.8

  In order to search target organs and to study the mechanism of the action of steroids with separated biological functions, tritium-labeled pregna-D'-pentaranes were synthesized by an original procedure, and their interaction with a progesterone receptor was investigated. The uterine progesterone receptor was shown to be the only specific binding protein for these compounds.
• 3- and 19-Oximes of 16α,17α-cyclohexanoprogesterone derivatives: Synthesis and interactions with progesterone receptor and other proteins
  作者：Inna S. Levina、Elena V. Pokrovskaya、Lidya E. Kulikova、Alexey V. Kamernitzky、Vadim V. Kachala、Alexander N. Smirnov

  DOI：10.1016/j.steroids.2008.03.003

  日期：2008.9

  Series of 3- and 19-oximes of 16 alpha,17 alpha-cyclohexanoprogesterone derivatives (pregna-D'-pentaranes) have been synthesized with the aim of probing the surfaces of progesterone receptor's and two other protein ligand binding pockets neighboring to 3- and 19-positions of steroid core. The same derivatives were also studied as possible intermediates for attachment to matrixes. The data on affinity constants suggest the presence of hydrophobic cavities with hydrophilic necks in the progesterone receptor and serum pentaranophylin near C19 of bound ligand and the lack of such a cavity in uterine pentaranophylin. Any of 3-oxime substitutions were found to significantly diminish the ligand affinity for the progesterone receptor. It was also found that some of these modifications, in the Z-configuration particularly, might increase the affinity for serum and uterine pentaranophylins. The latter finding suggests the presence of large cavities near C3 of bound ligand in these proteins and interchangeability between 3-keto and 3-oxime groups in ligand-protein interactions. (C) 2008 Elsevier Inc. All rights reserved.
• Biological activity of transformed steroids XV. Synthesis and hormonal activity of 6-methyl-substituted 16α, 17α-cyclohexanoprogesterones
  作者：A. V. Kamernitskii、L. E. Kulikova、I. S. Levina、V. V. Korkhov、G. V. Nikitina

  DOI：10.1007/bf01156378

  日期：1980.9
• Synthesis of 6α-methyl-16α, 17α-cyclohexanoprogesteronevia γ-methylenation of 16α, 17α-cyclohexanopregn-4-ene-3,20-dione
  作者：I. S. Levina、A. V. Kamernitskii

  DOI：10.1007/bf02496229

  日期：1997.6

  6-Methylene-16 alpha,17 alpha-cyclohexanopregn-4-ene-3,20-dione 2 has been synthesized by the reaction of Delta(4)-3-ketone 1 with CH2(OEt)(2) and POCl3 in the presence of AcONa in 55% yield. Reduction of the product 2 in the presence of 5% Pd/C gives 6 alpha-methyl-16 alpha,17 alpha-cyclohexanoprogesterone 3 in a yield exceeding 70%.
• 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