5-methyl-17-oxo-19-nor-5β,9α,10β-androstan-3β-yl acetate | 181930-97-2

• 分子结构分类: 有机化合物
• 英文名称: 5-methyl-17-oxo-19-nor-5β,9α,10β-androstan-3β-yl acetate
• 英文别名: [(3S,5R,8R,9S,10R,13S,14S)-5,13-dimethyl-17-oxo-1,2,3,4,6,7,8,9,10,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 181930-97-2
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: FZJBOGGPGPIRRE-BJFZXJCHSA-N

物化性质

• 沸点：
  424.6±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  5-methyl-17-oxo-19-nor-5β,9α,10β-androstan-3β-yl acetate 在 samarium diiodide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 Acetic acid (3S,5R,8R,9S,10R,13S,14S,17R)-17-cyano-5,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  Neurosteroid Analogues. 4. The Effect of Methyl Substitution at the C-5 and C-10 Positions of Neurosteroids on Electrophysiological Activity at GABA_A Receptors

  摘要：

  A series of analogues of the neuroactive steroids 3 alpha-hydroxy-5 alpha-pregnan-20-one and 3 alpha-hydroxy-5 beta-pregnan-20-one were studied to elucidate the mode of binding of 5 alpha- and 5 beta-reduced steroids to steroid binding sites on GABA(A) receptors. Analogues which were either 3 alpha-hydroxy-20-ketosteroids or 3 alpha-hydroxysteroid-17 beta-carbonitriles and which contained various methyl group substitution patterns at C-5 and C-10 were prepared. Evaluations utilized whole-cell patch clamp electrophysiological methods carried out on cultured rat hippocampal neurons, and the results obtained with the rigid 17 beta-carbonitrile analogs were analyzed using molecular modeling methods. The molecular modeling results provide a rationale for the observation that the configuration of the hydroxyl group at C-3 is a greater determinant of anesthetic potency than the configuration of the A,B ring fusion at C-5. The electrophysiological results identify steric restrictions for the space that can be occupied in 5 alpha- and 5 beta-reduced steriod modulators of GABA(A) receptors in the regions of space proximate to the steroid C-5, C-10, and possibly C-4 positions. This information is useful for the development of nonsteroidal analogues that can modulate GABA(A) receptors via interactions at steroid binding sites.

  DOI：

  10.1021/jm960304p
• 作为产物：
  描述：

  5-methyl-17-oxo-19-nor-5β-androst-9-en-3β-yl acetate 在 platinum(IV) oxide 吡啶 、 jones reagent 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醇 、 溶剂黄146 、 丙酮 为溶剂， 反应 39.67h， 生成 5-methyl-17-oxo-19-nor-5β,9α,10β-androstan-3β-yl acetate
  参考文献：
  名称：

  Analogues of androgen hormones with inverted configuration at carbons 5, 9, and 10

  摘要：

  On catalytic hydrogenation of Delta (9)-steroids (e.g. 3 beta -hydroxy-5-methyl-19-nor-5 beta -androst-9-en-17-one), four isomers were formed: 9 alpha ,10 alpha-, 9 alpha ,10 beta-, 9 beta ,10 alpha- and 9 beta ,10 beta -adducts. The product distribution was affected by the nature of the C-3 substituent. A chair conformation of A, B, and C rings was found in all of the products with the exception of the 9 alpha ,10 alpha -adduct whose B ring adopts a twist boat conformation. The products were utilized for the synthesis of dihydrotestosterone analogues. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00135-0