?9,11-去氢-17alpha-氰基甲基雌二醇 | 86153-38-0

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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: ?9,11-去氢-17alpha-氰基甲基雌二醇
• 英文名称: 17α-Cyanomethylestra-1,3,5(10),9(11)-tetraen-3,17β-diol
• 英文别名: 17α-cyanomethyl-1,3,5(10),9(11)-estratetraene-3,17-diol；J 1201；Dienogest Impurity G；2-[(8S,13S,14S,17R)-3,17-dihydroxy-13-methyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-yl]acetonitrile
• CAS: 86153-38-0
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: LPEAVAOTAWKUPC-FUMNGEBKSA-N

物化性质

• 熔点：
  228 - 233°C
• 沸点：
  551.2±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶）、甲醇（微溶、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  64.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  地诺孕素 在 氢氧化钾 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 48.5h， 生成 ?9,11-去氢-17alpha-氰基甲基雌二醇
  参考文献：
  名称：

  Hubner; Menzenbach; Rohrig, Pharmazie, 1984, vol. 39, # 7, p. 496 - 496

  摘要：

  DOI：

文献信息

• Microbial transformation of 17α-cyanomethyl-17-hydroxy-4,9-estradien-3-one (STS 557) and 17α-cyanomethyl-19-nortestosterone by Mycobacterium smegmatis
  作者：G. Hobe、R. Schön、C. Hörhold、M. Hübner、W. Schade、K. Schubert

  DOI：10.1016/0039-128x(82)90064-2

  日期：1982.4

  Microbial transformation of the new progestagen STS 557 (17 alpha-cyanomethyl-17-hydroxy-4,9-estradien-3-one) by Mycobacterium smegmatis yielded predominantly ring A-aromatized compounds: 17 alpha-cyanomethyl-1,3,5(10),9(11)-estratetraene-3, 17-diol, 17 alpha-cyanomethyl-1,3,5(10)-estratriene-3,17-diol and the corresponding 3-methyl ethers. The analogous compound without the 9(10) double bond, 17 alpha-cyanomethyl-19-nortestosterone, was transformed mainly to 5 alpha-hydrogenated metabolites: 17 alpha-cyanomethyl-17-hydroxy-5 alpha-estran-3-one, 17 alpha-cyanomethyl-17-hydroxy-5 alpha-1-estren-3-one, 17 alpha-cyanomethyl-5 alpha-estrane-3 alpha, 17-diol, and 17 alpha-cyanomethyl-5 alpha-estrane-3 beta, 17-diol. From these results, it is concluded that 4,9-dien-3-oxo compounds are not substrates for enzymatic 5 alpha-hydrogenation.
• Nitrile hydratase from Rhodococcus erythropolis: Metabolization of steroidal compounds with a nitrile group
  作者：Günter Kaufmann、Horst Dautzenberg、Harry Henkel、Gerd Müller、Thomas Schäfer、Bernd Undeutsch、Michael Oettel

  DOI：10.1016/s0039-128x(99)00028-8

  日期：1999.8

  The progestin dienogest (17 alpha-cyanomethyl-17 beta-hydroxy-estra-4,9-dien-3-one) was metabolized by the nitrile hydratase-containing microorganism Rhodococcus erythropolis. An enzymatic hydrolysis of the nitrile group at the 17 alpha-side chain was intended to obtain novel derivatives and to test them for progesterone receptor affinity. In contrast to the rapid enzymatic hydrolysis of nonsteroidal nitriles, the nitrile group of dienogest was cleaved very slowly. The dominant reaction was an aromatization of ring A. After prolonged fermentation, the 17 alpha-acetamido derivatives of estradiol and of 9(11)-dehydroestradiol were formed. Three of the metabolites were also prepared synthetically. They were tested for hormonal activity by assessing their binding to progesterone and estrogen receptors in vitro. Neither the aromatized 17 alpha-acetamido derivatives nor the dienogest derivative 17 alpha-acetamido-17 beta-hydroxy-estra-4,9-dien-3-one, which was prepared synthetically only, exhibited affinity for the progesterone receptor. (C) 1999 Elsevier Science Inc. All fights reserved.
• Urinary metabolites of the new progestagen STS 557 (17α-cyanomethyl-17-hydroxy-4,9-estradien-3-one) in the dog and rat
  作者：G. Hobe、R. Schön、G. Frankenberg、W. Schade、K. Schubert

  DOI：10.1016/0039-128x(83)90013-2

  日期：1983.1

  Urinary metabolites of the new progestagen STS 557 (17 alpha-cyanomethyl-17-hydroxy-4,9-estradien-3-one) were isolated and characterized following oral administration of the 14 alpha, 15 alpha-tritium labelled compound to dogs and rats. 17 alpha-Cyanomethyl-11 beta, 17-dihydroxy-4,9-estradien-3-one (11 beta-OH-STS 557) and 17 alpha-cyanomethyl-1,3,5(10),9(11)-estratetraene-3,17-diol were identified by comparison with synthesized reference compounds. Mass spectra data indicate the following other pathways of STS 557 biotransformation: Hydroxylation in other positions than 11; hydrogenation; hydroxylation + hydrogenation; alteration of the 17 alpha-side chain.
• Hubner; Menzenbach; Rohrig, Pharmazie, 1984, vol. 39, # 7, p. 496 - 496
  作者：Hubner、Menzenbach、Rohrig、Ponsold

  DOI：——

  日期：——