11β-Aethyl-4-estren-17-on | 67020-52-4

• 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: 11β-Aethyl-4-estren-17-on
• 英文别名: (8R,9S,10R,11S,13S,14S)-11-ethyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-one
• CAS: 67020-52-4
• 化学式: C₂₀H₃₀O
• 分子量: 286.458
• InChiKey: BJVKXHMWJZNEMQ-RDNJYJPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  11β-Aethyl-4-estren-17-on 、 乙炔 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 17α-Ethynyl-11β-ethyl-4-estren-17β-ol
  参考文献：
  名称：

  Strategy in drug reseabch. Synthesis and study of the psogestational and ovulation inhibitory activity of a series of 11β-substituted-17α-ethynyl-4-estren-17β-ols

  摘要：

  Using the strategy based on the Hansch method which analyses effects of substituents on biological activity in terms of their hydrophobic, electronic and steric effects we selectively synthesised a series of 11beta-substituted-17alpha-ethynyl-4-estren-17beta-ols that combine ease of synthesis with good discrimination between these factors aiming at finding the compounds with optimum biological activity in that series. The compounds were tested quantitatively in the Clauberg test (rabbit) and the ovulation inhibition test (rat). The differences in biological activity could reasonably be correlated with two steric effects introduced by the 11beta-substituent. These were a change in the overall shape of the 11beta-substituent and the angular methyl group, and direct steric hindrance of the steroid-receptor protein binding. Some exceptions were found possibly due to metabolic conversion of these compounds to the corresponding 11beta-substituted-17alpha-ethynyl-1,3,5(10)-estra-triene-3,17beta-diols.

  DOI：

  10.1016/0039-128x(77)90095-2
• 作为产物：
  描述：

  11β-Ethyl-4-estren-17β-ol 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 11β-Aethyl-4-estren-17-on
  参考文献：
  名称：

  Strategy in drug reseabch. Synthesis and study of the psogestational and ovulation inhibitory activity of a series of 11β-substituted-17α-ethynyl-4-estren-17β-ols

  摘要：

  Using the strategy based on the Hansch method which analyses effects of substituents on biological activity in terms of their hydrophobic, electronic and steric effects we selectively synthesised a series of 11beta-substituted-17alpha-ethynyl-4-estren-17beta-ols that combine ease of synthesis with good discrimination between these factors aiming at finding the compounds with optimum biological activity in that series. The compounds were tested quantitatively in the Clauberg test (rabbit) and the ovulation inhibition test (rat). The differences in biological activity could reasonably be correlated with two steric effects introduced by the 11beta-substituent. These were a change in the overall shape of the 11beta-substituent and the angular methyl group, and direct steric hindrance of the steroid-receptor protein binding. Some exceptions were found possibly due to metabolic conversion of these compounds to the corresponding 11beta-substituted-17alpha-ethynyl-1,3,5(10)-estra-triene-3,17beta-diols.

  DOI：

  10.1016/0039-128x(77)90095-2

文献信息

• Steroids with a 17-spiromethylene lactone or lactol group
  申请人：Akzo Nobel N.V.

  公开号：EP0709394A2

  公开（公告）日：1996-05-01

  A steroid with a 17-spiromethylene lactone group having formula I wherein R₁ is O, (H,H), (H,OR), or NOR, R being selected from H, (1-6C) alkyl and (1-6C) acyl; R₂ is H, (1-6C) alkyl optionally substituted by a halogen, (2-6C) alkenyl optionally substituted by a halogen, (2-6C) alkynyl optionally substituted by a halogen, or halogen; R₂' is H; or R₂' together with R₂ is a (1-6C) alkylidene group or a (2-6C) alkenylidene group; or R₂' together with R₃ is a bond; R₃ is H if not together with R₂' a bond; R₄ is (1-6C) alkyl; one of R₅ and R₆ is hydrogen and the other is hydrogen or (1-6C) alkyl; X is (CH₂)n or (CnH2n-2) wherein n is 2 or 3, which is optionally substituted with hydroxy, halogen, (1-6C) alkyl, (1-6C) acyl, (7-9C) phenylalkyl, the phenyl group of which may be substituted with (1-6C) alkyl, (1-6C) alkoxy, hydroxy or halogen; Y is O or (H,OH); and the dotted lines indicate optional bonds, at least one of bonds 4-5, 5-10, and 9-10 being a double bond. The steroids of the invention have progestational activity and can be used as contraceptives.

  一种具有式 I 的 17-螺亚甲基内酯基团的类固醇 其中 R₁ 是 O、(H,H)、(H,OR)或 NOR，R 选自 H、(1-6C)烷基和(1-6C)酰基；R₂ 是 H、任选被卤素取代的(1-6C)烷基、任选被卤素取代的(2-6C)烯基、任选被卤素取代的(2-6C)炔基或卤素；R₂' 是 H；或 R₂' 与 R₂ 一起是 (1-6C) 亚烷基或 (2-6C) 亚烯基；或 R₂' 与 R₃ 一起是键；如果 R₃ 与 R₂' 不是键，则是 H；R₄ 是 (1-6C) 烷基；R₅ 和 R₆ 中的一个是氢，另一个是氢或 (1-6C) 烷基；X 是 (CH₂)n 或 (CnH2n-2)，其中 n 是 2 或 3，可任选被羟基、卤素、(1-6C)烷基、(1-6C)酰基、(7-9C)苯基烷基取代，其中苯基可被(1-6C)烷基、(1-6C)烷氧基、羟基或卤素取代；Y 是 O 或（H,OH）；虚线表示任选的键，键 4-5、5-10 和 9-10 中至少有一个是双键。 本发明的类固醇具有孕激素活性，可用作避孕药。
• US5741786A
  申请人：——

  公开号：US5741786A

  公开（公告）日：1998-04-21
• Strategy in drug reseabch. Synthesis and study of the psogestational and ovulation inhibitory activity of a series of 11β-substituted-17α-ethynyl-4-estren-17β-ols
  作者：A.J.v.d. Broek、A.I.A. Broess、M.J.v.d. Heuvel、H.P. de Jongh、J. Leemhuis、K.H. Schonemann、J. Smits、J. de Visser、N.P. van Vliet、F.J. Zeelen

  DOI：10.1016/0039-128x(77)90095-2

  日期：1977.10

  Using the strategy based on the Hansch method which analyses effects of substituents on biological activity in terms of their hydrophobic, electronic and steric effects we selectively synthesised a series of 11beta-substituted-17alpha-ethynyl-4-estren-17beta-ols that combine ease of synthesis with good discrimination between these factors aiming at finding the compounds with optimum biological activity in that series. The compounds were tested quantitatively in the Clauberg test (rabbit) and the ovulation inhibition test (rat). The differences in biological activity could reasonably be correlated with two steric effects introduced by the 11beta-substituent. These were a change in the overall shape of the 11beta-substituent and the angular methyl group, and direct steric hindrance of the steroid-receptor protein binding. Some exceptions were found possibly due to metabolic conversion of these compounds to the corresponding 11beta-substituted-17alpha-ethynyl-1,3,5(10)-estra-triene-3,17beta-diols.