4-雌烯-6beta,17beta-二醇-3-酮 | 4146-29-6

• 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: 4-雌烯-6beta,17beta-二醇-3-酮
• 英文名称: 6β,17β-dihydroxy-19-nor-4-androsten-3-one
• 英文别名: 6β,17β-dihydroxy-19-norandrost-4-en-3-one；6β,17β-dihydroxyestr-4-en-3-one；6β-hydroxy-19-nortestosterone；6β-hydroxynortestosterone；6β,17β-dihydroxy-estr-4-en-3-one；6β,17β-Dihydroxy-oestr-4-en-3-on；(6R,8R,9S,10R,13S,14S,17S)-6,17-Dihydroxy-13-methyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one；(6R,8R,9S,10R,13S,14S,17S)-6,17-dihydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 4146-29-6
• 化学式: C₁₈H₂₆O₃
• 分子量: 290.403
• InChiKey: JBXQPIRHIYLCNL-RYJUIXMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-雌烯-6beta,17beta-二醇-3-酮 在 chromium(VI) oxide 、 硫酸 、 丙酮 作用下， 生成 雌-4-烯-3,6,17-三酮
  参考文献：
  名称：

  MICROBIOLOGICAL TRANSFORMATIONS OF STEROIDS. XIV.¹ THE PREPARATION OF A TERTIARY HYDROXY-STEROID, 10ξ-HYDROXY-19-NORTESTOSTERONE

  摘要：

  DOI：

  10.1021/ja01588a068
• 作为产物：
  描述：

  诺龙 生成 4-雌烯-6beta,17beta-二醇-3-酮
  参考文献：
  名称：

  MICROBIOLOGICAL TRANSFORMATIONS OF STEROIDS. XIV.¹ THE PREPARATION OF A TERTIARY HYDROXY-STEROID, 10ξ-HYDROXY-19-NORTESTOSTERONE

  摘要：

  DOI：

  10.1021/ja01588a068

文献信息

• Biotransformation of 19-Nortestosterone by <i>Aspergillus Wentii</i> MRC 200316
  作者：Kudret Yildirim、Cagla Ayhan

  DOI：10.3184/174751912x13418486956512

  日期：2012.9

  Incubation of 19-nortestosterone 1 with Aspergillus wentii MRC 200316 for 5 days afforded 10β-hydroxy-19-nortestosterone 2 (2%), 6β-hydroxy-19-nortestosterone 3 (60%), and 14α-hydroxy-19-nortestosterone 4 (5%).

  将 19-去甲睾酮 1 与文氏曲霉 MRC 200316 培养 5 天，可得到 10β-羟基-19-去甲睾酮 2（2%）、6β-羟基-19-去甲睾酮 3（60%）和 14α-羟基-19-去甲睾酮 4（5%）。
• Microbial transformation of nandrolone with Cunninghamella echinulata and Cunninghamella blakesleeana and evaluation of leishmaniacidal activity of transformed products
  作者：Elias Baydoun、Martin Karam、Atia-tul-Wahab、Mahwish Shafi Ahmed Khan、Malik Shoaib Ahmad、Samreen、Colin Smith、Roula Abdel-Massih、M. Iqbal Choudhary

  DOI：10.1016/j.steroids.2014.06.020

  日期：2014.10

  Therapeutic potential of nandrolone and its derivatives against leishmaniasis has been studied. A number of derivatives of nandrolone (1) were synthesized through biotransformation. Microbial transformation of nandrolone (1) with Cunninghamella echinulata and Cunninghamella blakesleeana yielded three new metabolites, 10β,12β,17β-trihydroxy-19-nor-4-androsten-3-one (2), 10β,16α,17β-trihydroxy-19-nor-4-androsten-3-one

  已经研究了诺龙及其衍生物对利什曼病的治疗潜力。通过生物转化合成了许多诺龙 (1) 的衍生物。诺龙 (1) 与 Cunninghamella echinulata 和 Cunninghamella blakesleeana 的微生物转化产生了三种新的代谢物，10β,12β,17β-trihydroxy-19-nor-4-androsten-3-one (2), 10β,16α,17β-trihydroxy-19 -nor-4-androsten-3-one (3) 和 6β,10β,17β-trihydroxy-19-nor-4-androsten-3-one (4)，以及四种已知的代谢物，10β,17β-dihydroxy- 19-nor-4-androsten-3-one (5), 6β,17β-dihydroxy-19-nor-4-androsten-3-one (6) 10β-hyd
• Transformations of 4- and 17α-substituted testosterone analogues by
  作者：A SWIZDOR、T KOLEK

  DOI：10.1016/j.steroids.2005.05.005

  日期：2005.11

  been incubated with the hydroxylating fungus Fusarium culmorum AM282. It was found that 19-norandrostenedione, 19-nortestosterone, 4-methoxytestosterone, 4-methyltestosterone, and 4-chloro-17alpha-methyltestosterone were hydroxylated exclusively or mainly at the 6beta-position. The mixtures of 6beta-, 15alpha-, and 12beta- or 11alpha-monohydroxy derivatives were obtained from 17alpha-methyltestosterone

  一系列的4-和/或17α-取代的睾丸激素类似物已与羟基化真菌镰刀菌AM282一起温育。发现19-去甲烯二烯二酮，19-去甲睾酮，4-甲氧基睾丸酮，4-甲基睾丸酮和4-氯-17α-甲基睾丸酮仅或主要在6β-位被羟基化。6beta-，15alpha-和12beta-或11alpha-单羟基衍生物的混合物是从17alpha-甲基睾丸激素和17alpha-乙基-19-睾丸激素-在C-17alpha处具有烷基的底物获得的。4-氯睾酮主要在15α-位羟基化，但反应伴随着4-en-3-one系统的还原，其顺序如下：将酮还原为3beta-醇，然后还原双4， 5键。
• de Flines,J. et al., Recueil des Travaux Chimiques des Pays-Bas, 1963, vol. 82, p. 149 - 156
  作者：de Flines,J. et al.

  DOI：——

  日期：——
• The hydroxylation of testosterone and some relatives by Cephalosporium aphidicola
  作者：James R. Hanson、Habib Nasir、Aslam Parvez

  DOI：10.1016/0031-9422(95)00968-x

  日期：1996.5

  The fungus Cephalosporium aphidicola has been shown to hydroxylate testosterone, 19-nortestosterone, 1-dehydrotestosterone, 1 alpha-methyltestosterone, androst-4-en-3-one, androst-4-en-3,17-dione and 17 alpha-methyltestosterone predominantly at the C-6 beta position with a minor hydroxylation occurring at the C-14 alpha position. 19-Nortestosterone was also hydroxylated at the C-10 beta position. In contrast to the hydroxylation of progesterone by this organism, hydroxylation at C-11 alpha was a minor pathway.