3β-Hydroxy-19-iodo-5-androsten-17-one acetate | 82341-96-6

• 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
• 英文名称: 3β-Hydroxy-19-iodo-5-androsten-17-one acetate
• 英文别名: 19-Iodo-5-androstene-3beta-ol-17-one 3-acetate；[(3S,8S,9S,10S,13S,14S)-10-(iodomethyl)-13-methyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 82341-96-6
• 化学式: C₂₁H₂₉IO₃
• 分子量: 456.364
• InChiKey: CSKDQVBRIWZGLL-JPRZGNOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.809
• 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：

  3β-Hydroxy-19-iodo-5-androsten-17-one acetate 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 为溶剂， 反应 5.0h， 生成 19-甲硫基雄甾-4-烯-3,17-二酮
  参考文献：
  名称：

  甾体C-19硫和氮衍生物设计为芳香酶抑制剂

  摘要：

  该甾族化合物（在发现6）和（15）在19位上的碘被平稳地通过反应性亲核置换（CN - ，内消旋2小号-，N 3 - ），而不重排是在19甲硫的合成利用示出了-4-甾烷-3，17-二酮（14），其通过甾族硫原子与细胞色素P-450的血红素铁的配位而抑制芳香化酶。

  DOI：

  10.1039/c39850001733
• 作为产物：
  描述：

  3β,19-dihydroxy-5-androsten-17-one 3-acetate 19-p-toluenesulfonate 在 sodium iodide 作用下， 以 异丙醇 为溶剂， 反应 3.0h， 以1.1 g的产率得到3β-Hydroxy-19-iodo-5-androsten-17-one acetate
  参考文献：
  名称：

  131I-labeled 19-iodinated and 6β-iodomethyl-19-nor steroids: effect of structural modification on the adrenal accumulation

  摘要：

  19-Iodinated and 6 beta-iodomethyl-19-nor derivatives of cholesterol and 17-ketosteroid labeled with 131I were tested in rats to determine the critical structural features required for maximal adrenal uptake. The introduction of the 17-keto group in place of the 17 beta-side chain of cholesterol caused most of the radioactivity to be taken up by the thyroids. Fluorination at the C-3 position had deleterious effects on the adrenal concentration and led to the loss of adrenal specificity. A beta-hydroxy group at the C-3 position is substantially required for adrenal uptake.

  DOI：

  10.1016/0039-128x(83)90002-8

文献信息

• WRIGHT, J. NEVILLE;VAN, LEERSUM PHILLIP T.;CHAMBERLIN, STEPHEN G.;AKHTAR,+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N, C. 1647-1655
  作者：WRIGHT, J. NEVILLE、VAN, LEERSUM PHILLIP T.、CHAMBERLIN, STEPHEN G.、AKHTAR,+

  DOI：——

  日期：——
• Steroidal C-19 sulphur and nitrogen derivatives designed as aromatase inhibitors
  作者：J. Neville Wright、Michael R. Calder、Muhammad Akhtar

  DOI：10.1039/c39850001733

  日期：——

  The discovery that in the steroidal compounds (6) and (15) iodine in the 19-position is smoothly displaced by reactive nucleophiles (CN–, MeSO2S–, N3–) without rearrangement was exploited in the synthesis of 19-methylthio-4-androstene-3,17-dione (14) which was shown to inhibit aromatase by co-ordination of the steroidal sulphur atom to the haem-iron of cytochrome P-450.

  该甾族化合物（在发现6）和（15）在19位上的碘被平稳地通过反应性亲核置换（CN - ，内消旋2小号-，N 3 - ），而不重排是在19甲硫的合成利用示出了-4-甾烷-3，17-二酮（14），其通过甾族硫原子与细胞色素P-450的血红素铁的配位而抑制芳香化酶。
• 131I-labeled 19-iodinated and 6β-iodomethyl-19-nor steroids: effect of structural modification on the adrenal accumulation
  作者：Takayuki Ito、Hiroshi Ogawa、Minoru Maeda、Masaharu Kojima

  DOI：10.1016/0039-128x(83)90002-8

  日期：1983.2

  19-Iodinated and 6 beta-iodomethyl-19-nor derivatives of cholesterol and 17-ketosteroid labeled with 131I were tested in rats to determine the critical structural features required for maximal adrenal uptake. The introduction of the 17-keto group in place of the 17 beta-side chain of cholesterol caused most of the radioactivity to be taken up by the thyroids. Fluorination at the C-3 position had deleterious effects on the adrenal concentration and led to the loss of adrenal specificity. A beta-hydroxy group at the C-3 position is substantially required for adrenal uptake.