(16beta,17alpha)-17-乙酰基-16,24-环-21-去甲胆-4-烯-3-酮 | 38522-51-9

• 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: (16beta,17alpha)-17-乙酰基-16,24-环-21-去甲胆-4-烯-3-酮
• 英文名称: [3H]-Pentarane A
• 英文别名: Pentarane A；16α,17α-cyclohexanopregn-4-ene-3,20-dione；16α,17α-cyclohexanoprogesterone；(4aR,4bS,6aS,6bS,10aR,11aS,11bR)-6b-acetyl-4a,6a-dimethyl-4,4b,5,6,7,8,9,10,10a,11,11a,11b,12,13-tetradecahydro-3H-indeno[2,1-a]phenanthren-2-one
• CAS: 38522-51-9
• 化学式: C₂₅H₃₆O₂
• 分子量: 368.56
• InChiKey: QRVBGQLTPQQFJY-IEHCJHDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  (16beta,17alpha)-17-乙酰基-16,24-环-21-去甲胆-4-烯-3-酮 在 苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 10.0h， 以76%的产率得到16α,17α-cyclohexanopregna-1,4-diene-3,20-dione
  参考文献：
  名称：

  Catalysis by lewis acids at high pressure as a method of involving hindered steroid dienophiles in the diels?Alder reaction

  摘要：

  The joint action of Lewis acids and high pressure permits the Diels-Alder reaction to be conducted with high yields with greatly sterically hindered steroid dienophiles, which are virtually unreactive under normal conditions. The [2 + 4]-cycloadditions of dienes to DELTA16-20-, DELTA1-3-, DELTA1,4-3-, and DELTA4,6-3-ketones proceed stereospecifically with the formation of one stereoisomer for each cycloadduct. The reactions of the steroid dienes studied give mixtures of two monocycloadducts at both double bonds of the steroid, with predominance of the adduct at the sterically less-hindered double bond (DELTA1- and DELTA6-). The method developed is a new method of producing various modified steroids with possible hormonal or antihormonal activity.

  DOI：

  10.1007/bf00864191

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
• Synthesis of 4-hetero-16α,17α-cyclohexanopregnanes and evaluation of their cytotoxicity against the HeLa cell line
  作者：I. S. Levina、L. E. Kulikova、A. V. Semeikin、I. V. Zavarzin

  DOI：10.1007/s11172-018-2336-8

  日期：2018.11

  5-oxo-A-nor-3,5-secopregnan-3-oic acid. The subsequent ring A closure in the latter compound upon treatment with sodium acetate in Ac2O afforded 4-oxasteroid. The reaction with ammonium acetate in acetic acid produced 4-azasteroid. Antiproliferative activity of the resulting steroids against cervical cancer HeLa cells and the in vitro binding to the progesterone receptor were studied. The compounds cause

  16α,17α-环己孕酮的A环氧化得到5-氧代-A-nor-3,5-secopregnan-3-oic酸。在用 Ac2O 中的乙酸钠处理后，后一种化合物中的 A 环闭合得到 4-氧杂甾类。在乙酸中与乙酸铵反应生成4-氮杂甾体。研究了所得类固醇对宫颈癌 HeLa 细胞的抗增殖活性和与孕酮受体的体外结合。这些化合物导致宫颈癌 HeLa 细胞活力在统计学上显着降低，对正常皮肤成纤维细胞没有影响。测试的类固醇显示与大鼠子宫孕酮受体的结合非常低。
• 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%.
• 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.
• 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.