17β-Acetoxy-1,2,3,4-tetranor-Δ9-androstenon-(5) | 19614-35-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 17β-Acetoxy-1,2,3,4-tetranor-Δ9-androstenon-(5)
• 英文别名: 17β-Acetoxy-1,2,3,4-tetranor-Δ⁹-androstenon-(5)
• CAS: 19614-35-8
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: ZZDNZIHXSBLGTL-OHFALNGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  17β-Acetoxy-1,2,3,4-tetranor-Δ9-androstenon-(5) 在 氢氧化钾 、 氨 、 lithium 作用下， 以 甲醇 为溶剂， 反应 3.83h， 生成 (3S,3aS,5aS,6S,9aS,9bS)-3-Hydroxy-3a,6-dimethyl-6-propyl-dodecahydro-cyclopenta[a]naphthalen-7-one
  参考文献：
  名称：

  Antiandrogenic activity of a series of des-A-steroid derivatives

  摘要：

  In the search for new antiandrogens, a number of des-A-steroids were prepared by condensation of Grignard reagents with lactone 3. From the resulting key intermediates 5, various structural modifications were performed such as the introduction of an additional unsaturation to afford dienones 8 and aromatic derivatives 10 or the introduction of an alkyl substituent mostly in position 10 (11-13) but also in some cases in position 16 (22). In addition, 13-ethyl analogues were also prepared from lactone 4. The relative binding affinities (RBAs) for the androgen receptor of these compounds were determined under various conditions. Some compounds exhibit a capacity to interact with the receptor comparable to that of testosterone. One of the most potent compounds is 17beta-hydroxy-des-A-androsta-9,11-dien-5-one (8b), RBA value 73% of that of testosterone. More interestingly, several compounds were found to have an antiandrogenic profile in vitro and in vivo. One of the most effective compounds is 10-ethyl-17beta-hydroxy-des-A-estra-9-en-5-one (5c), which exhibits a strong local antiandrogenic activity in hamsters, without any significant systemic antiandrogenic effects. The corresponding 17beta-acetyl derivative (RU 38882) has been selected for extended pharmacological studies.

  DOI：

  10.1021/jm00150a009
• 作为产物：
  描述：

  乙基溴化镁 、 Acetic acid (3S,3aS,9aS,9bS)-3a-methyl-7-oxo-1,2,3,3a,4,7,8,9,9a,9b-decahydro-6-oxa-cyclopenta[a]naphthalen-3-yl ester 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 17β-Acetoxy-1,2,3,4-tetranor-Δ9-androstenon-(5)
  参考文献：
  名称：

  Antiandrogenic activity of a series of des-A-steroid derivatives

  摘要：

  In the search for new antiandrogens, a number of des-A-steroids were prepared by condensation of Grignard reagents with lactone 3. From the resulting key intermediates 5, various structural modifications were performed such as the introduction of an additional unsaturation to afford dienones 8 and aromatic derivatives 10 or the introduction of an alkyl substituent mostly in position 10 (11-13) but also in some cases in position 16 (22). In addition, 13-ethyl analogues were also prepared from lactone 4. The relative binding affinities (RBAs) for the androgen receptor of these compounds were determined under various conditions. Some compounds exhibit a capacity to interact with the receptor comparable to that of testosterone. One of the most potent compounds is 17beta-hydroxy-des-A-androsta-9,11-dien-5-one (8b), RBA value 73% of that of testosterone. More interestingly, several compounds were found to have an antiandrogenic profile in vitro and in vivo. One of the most effective compounds is 10-ethyl-17beta-hydroxy-des-A-estra-9-en-5-one (5c), which exhibits a strong local antiandrogenic activity in hamsters, without any significant systemic antiandrogenic effects. The corresponding 17beta-acetyl derivative (RU 38882) has been selected for extended pharmacological studies.

  DOI：

  10.1021/jm00150a009

文献信息

• Steroid Total Synthesis, Part III. 9?, 10?-Testosterone
  作者：G. Saucy、R. Borer

  DOI：10.1002/hlca.19710540815

  日期：1971.12.10

  AbstractThe total synthesis of 9β, 10α‐testosterone via a BCD‐tricyclic intermediate is described. The latter compound – 17β‐hydroxy‐des‐A‐androst‐9‐en‐5‐one – was obtained in optically active form by our previously reported scheme, using an efficient resolution step early in the synthesis. New results regarding the asymmetric induction step are also discussed.