16α-甲基孕烯醇酮乙酸酯 | 1863-41-8

• 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: 16α-甲基孕烯醇酮乙酸酯
• 英文名称: 3β-Acetoxy-16α-methyl-Δ⁵-pregnenon-(20)
• 英文别名: Pregn-5-en-20-one, 3beta-hydroxy-16alpha-methyl-, acetate；[(3S,8S,9S,10R,13S,14S,16R,17S)-17-acetyl-10,13,16-trimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 1863-41-8
• 化学式: C₂₄H₃₆O₃
• 分子量: 372.548
• InChiKey: SFNSGHUMGYWJGF-AWGTVLFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  16α-甲基孕烯醇酮乙酸酯 在 sodium hydroxide 作用下， 反应 1.0h， 以83%的产率得到16-alpha-甲基孕甾烯醇酮
  参考文献：
  名称：

  Stereoselective synthesis of some methyl-substituted steroid hormones and their in vitro cytotoxic activity against human gastric cancer cell line MGC-803

  摘要：

  A series of 3-, 7-, 15-, and 16-methyl-substituted steroid analogs were synthesized via a highly stereoselective 1,6-conjugate addition. Under the catalysis of CuBr, AlMe(3) reacted with four steroid dienone precursors to afford either the corresponding et-epimer of C-3 and C-7 methyl-substituted steroids as the major products, and the ratio of 43 was up to alpha/beta. No beta-epimer has been detected for methyl addition at C-16. However, under the same reaction conditions, enantioselective methyl addition at C-15 afforded the 15 beta-epimer as the major product. The preliminary SAR analysis showed that the methyl substituents at C-7 alpha and C-15 beta positions lead to a dramatical increase in potency against human gastric cancer cell line MGC-803. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.05.008
• 作为产物：
  描述：

  3'-H-cyclopropa<16,17α>pregn-5-en-3β-ol-20-one 3-acetate 在 氨 、 乙酸酐 、 lithium 作用下， 生成 16α-甲基孕烯醇酮乙酸酯
  参考文献：
  名称：

  Transformed steroids

  摘要：

  DOI：

  10.1007/bf00950306

文献信息

• [EN] C7, C12, AND C16 SUBSTITUTED NEUROACTIVE STEROIDS AND THEIR METHODS OF USE<br/>[FR] STÉROÏDES NEUROACTIFS SUBSTITUÉS EN C7, C12 ET C16 ET MÉTHODES D'UTILISATION ASSOCIÉES
  申请人：SAGE THERAPEUTICS INC

  公开号：WO2018013615A1

  公开（公告）日：2018-01-18

  Described herein are neuroactive steroids of Formula (I), Formula (V), or Formula (IX) or a pharmaceutically acceptable salt thereof; wherein each instance of R2, R3, R4, R5, R6, R7, R11a, R11b,R12, R16, R17, R19, and ----- are as defined herein. Such compounds are envisioned, in certain embodiments, to behave as GABA modulators. Also provided are pharmaceutical compositions comprising a compound described herein and methods of use and treatment, e.g., such as for inducing sedation and/or anesthesia.

  本文描述了化学式（I）、化学式（V）或化学式（IX）的神经活性类固醇或其药用盐；其中R2、R3、R4、R5、R6、R7、R11a、R11b、R12、R16、R17、R19和-----的每个实例如本文所定义。在某些实施例中，这些化合物被设想为GABA调节剂。还提供了包含本文描述的化合物的药物组合物以及使用和治疗方法，例如用于诱导镇静和/或麻醉。
• Reaction of nitrosyl fluoride and selected steroid enes. New synthesis of .DELTA.5-4-keto steroids
  作者：George A. Boswell

  DOI：10.1021/jo01274a005

  日期：1968.10
• Edwards et al., Proceedings of the Chemical Society, London, 1959, p. 87
  作者：Edwards et al.

  DOI：——

  日期：——
• Sterols. CXLIV. Some 16-Alkyl-pregnenolones and Progesterones¹
  作者：Russell E. Marker、Harry M. Crooks

  DOI：10.1021/ja01258a010

  日期：1942.6
• Autooxidation of Δ17(20)-20-hydroxy derivatives of steroids. Synthesis of 3β-acetoxy-17α-hydroperoxy-16α-methylpregn-5-en-20-one and its reduction to 17α-hydroxy derivative
  作者：T. S. Savinova、N. V. Lukashev、L. D. Huy、I. P. Beletskaya

  DOI：10.1134/s1070428011010052

  日期：2011.1

  An efficient procedure was proposed for the synthesis of 3 beta-acetoxy-17 alpha-hydroperoxy-16 alpha-methyl-pregn-5-en-20-one. Optimal conditions were found for the combined process including 1,4-addition of methyl-magnesium bromide at the Delta(16)-20-oxo fragment of dehydropregnenolone acetate and autooxidation of resulting bromomagnesium 3 beta-acetoxy-16 alpha-methylpregna-5,17(20)-dien-20-olate. The subsequent reduction of the 17 alpha-hydroperoxy group and hydrolysis of the 3 beta-acetoxy group afforded 17 alpha-hydroxy-16 alpha-methyl-substituted dehydropregnenolone acetate and its 3-hydroxy analog in high yield.