1-methyl-6-oxo-17β-estradiol | 17292-16-9

• 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: 1-methyl-6-oxo-17β-estradiol
• 英文别名: 3,17β-Dihydroxy-1-methyl-oestratrien-(1,3,5(10))-on-(6)；(8R,9S,13S,14S,17S)-3,17-dihydroxy-1,13-dimethyl-8,9,11,12,14,15,16,17-octahydro-7H-cyclopenta[a]phenanthren-6-one
• CAS: 17292-16-9
• 化学式: C₁₉H₂₄O₃
• 分子量: 300.398
• InChiKey: RRJQUPKONDIUPZ-MPFBVMFSSA-N

物化性质

• 熔点：
  312-315 °C(Solv: ethanol (64-17-5))
• 沸点：
  503.8±50.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 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：

  1-methyl-6-oxo-17β-estradiol 在 sodium methylate 作用下， 以 乙醇 、 苯 为溶剂， 生成 (8R,9S,13S,14S,17S)-3-[2-(dimethylamino)ethoxy]-1,13-dimethyl-6-phenyl-8,9,11,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-17-ol
  参考文献：
  名称：

  Potential steroidal antiestrogens

  摘要：

  A series of analogues of 17beta-estradiol has been synthesized and the compounds have been tested, using sucrose density gradient analysis, for their ability to compete with [6,7-3H]-17beta-estradiol for the estrogen-receptor protein from mouse uterine homogenates. Active compounds were also tested for antiuterotrophic activity in immature rats and/or mice. 3,17beta-Dihydroxy-6-phenylestra-1,3,5(10),6-tetraene (14) was the most active new compound in the in vitro test suppressing the binding of 17beta-estradiol by 34 and 87%, respectively, at molar ratios of 1 and 3.16. It was significantly more potent than the intermediate 6-oxoestradiol (4) which produced a 52% inhibition of binding at a molar ratio of 3.16. The thiosemicarbazone of 6-oxoestradiol (17) and the derived 3,17beta-dihydroxy-6-(2-imino-4-oxothiazolidinyl-1-imino)estra-1,3,5(10)-triene (19) produced, respectively, only 46 and 16% inhibition of binding at a molar ratio of 10. Introduction of a 1-methyl substituent into either 6-oxo or 6-phenyl compounds reduced affinity for the receptor significantly (compounds 5 and 15) and conversion of the 3-OH into a beta-dialkylaminoethoxy group virtually destroyed all binding activity (compounds 2, 6, 10, and 11). At a molar ratio of 10 compound 14 failed to suppress the uterine weight response of immature rats to 17beta-estradiol, whereas compound 15, at a molar ratio of 200, produced a significant increase in the uterine weight of immature rats but not of immature mice even at a molar ratio of 1000.

  DOI：

  10.1021/jm00218a022
• 作为产物：
  描述：

  3.17β-Diacetoxy-6β-hydroxy-7α-brom-1-methyl-oestratrien-(1.3.5,10) 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 1-methyl-6-oxo-17β-estradiol
  参考文献：
  名称：

  Pelc,B., Collection of Czechoslovak Chemical Communications, 1968, vol. 33, p. 314 - 318

  摘要：

  DOI：

文献信息

• Omar; Farghaly; Hazzai, Pharmazie, 1980, vol. 35, # 12, p. 809 - 810
  作者：Omar、Farghaly、Hazzai、Eshba

  DOI：——

  日期：——
• Potential steroidal antiestrogens
  作者：E. R. Clark、A. M. E. Omar、G. Prestwich

  DOI：10.1021/jm00218a022

  日期：1977.8

  A series of analogues of 17beta-estradiol has been synthesized and the compounds have been tested, using sucrose density gradient analysis, for their ability to compete with [6,7-3H]-17beta-estradiol for the estrogen-receptor protein from mouse uterine homogenates. Active compounds were also tested for antiuterotrophic activity in immature rats and/or mice. 3,17beta-Dihydroxy-6-phenylestra-1,3,5(10),6-tetraene (14) was the most active new compound in the in vitro test suppressing the binding of 17beta-estradiol by 34 and 87%, respectively, at molar ratios of 1 and 3.16. It was significantly more potent than the intermediate 6-oxoestradiol (4) which produced a 52% inhibition of binding at a molar ratio of 3.16. The thiosemicarbazone of 6-oxoestradiol (17) and the derived 3,17beta-dihydroxy-6-(2-imino-4-oxothiazolidinyl-1-imino)estra-1,3,5(10)-triene (19) produced, respectively, only 46 and 16% inhibition of binding at a molar ratio of 10. Introduction of a 1-methyl substituent into either 6-oxo or 6-phenyl compounds reduced affinity for the receptor significantly (compounds 5 and 15) and conversion of the 3-OH into a beta-dialkylaminoethoxy group virtually destroyed all binding activity (compounds 2, 6, 10, and 11). At a molar ratio of 10 compound 14 failed to suppress the uterine weight response of immature rats to 17beta-estradiol, whereas compound 15, at a molar ratio of 200, produced a significant increase in the uterine weight of immature rats but not of immature mice even at a molar ratio of 1000.
• Pelc,B., Collection of Czechoslovak Chemical Communications, 1968, vol. 33, p. 314 - 318
  作者：Pelc,B.

  DOI：——

  日期：——