3,3-(ethylenedioxy)-17α-methyl-5-androsten-17β-ol | 1099-72-5

• 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: 3,3-(ethylenedioxy)-17α-methyl-5-androsten-17β-ol
• 英文别名: 5-androst-17α-methyl-17β-hydroxy-3-ethylene ketal；3,3-ethanediyldioxy-17α-methyl-androst-5-en-17β-ol；3,3-Aethandiyldioxy-17α-methyl-androst-5-en-17β-ol；(8'R,9'S,10'R,13'S,14'S,17'S)-10',13',17'-trimethylspiro[1,3-dioxolane-2,3'-2,4,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-17'-ol
• CAS: 1099-72-5
• 化学式: C₂₂H₃₄O₃
• 分子量: 346.51
• InChiKey: DHYYILWASYVQLQ-CEGNMAFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3-(ethylenedioxy)-17α-methyl-5-androsten-17β-ol 在 palladium on activated charcoal 、 氢气 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 5α-androst-17α-methyl-17β-hydroxy-3-ethylene ketal
  参考文献：
  名称：

  雄甾-17α-甲基-17β-羟基-3-酮的制备方法

  摘要：

  一种雄甾‑17α‑甲基‑17β‑羟基‑3‑酮的制备方法，该方法是以甲睾酮为原料，经缩酮反应、催化氢化反应、水解反应得到雄甾‑17α‑甲基‑17β‑羟基‑3‑酮。本发明方法具有工艺简洁、生产成本低、产品纯度高、适合工业化生产的优点。

  公开号：

  CN109627274A
• 作为产物：
  描述：

  17-甲睾酮 、 乙二醇 在 三氟化硼乙醚 、 原甲酸三乙酯 作用下， 以 氯仿 为溶剂， 反应 9.0h， 以22.3 g的产率得到3,3-(ethylenedioxy)-17α-methyl-5-androsten-17β-ol
  参考文献：
  名称：

  雄甾-17α-甲基-17β-羟基-3-酮的制备方法

  摘要：

  一种雄甾‑17α‑甲基‑17β‑羟基‑3‑酮的制备方法，该方法是以甲睾酮为原料，经缩酮反应、催化氢化反应、水解反应得到雄甾‑17α‑甲基‑17β‑羟基‑3‑酮。本发明方法具有工艺简洁、生产成本低、产品纯度高、适合工业化生产的优点。

  公开号：

  CN109627274A

文献信息

• 6-Methyl Steroids in the Androstane Series¹
  作者：J Allan Campbell、John C. Babcock、John A. Hogg

  DOI：10.1021/ja01550a073

  日期：1958.9
• 7α-Iodo and 7α-Fluoro Steroids as Androgen Receptor-Mediated Imaging Agents
  作者：David C. Labaree、Robert M. Hoyte、Lynne V. Nazareth、Nancy L. Weigel、Richard B. Hochberg

  DOI：10.1021/jm990064o

  日期：1999.6.1

  We have synthesized several 7 alpha-fluoro (F) and 7 alpha-iodo (I) analogues of 5 alpha-dihydrotestosterone (5 alpha-DHT) and 19-nor-5 alpha-dihydrotestosterone (5 alpha-NDHT) and tested them for binding to the androgen receptor and for their biological activity in;an in vitro assay with cells that have been engineered to respond to androgens. The relative binding affinity to the androgen receptor determined in competition assays showed that in the androstane series the fluoro steroids have the highest affinity and that F-17 alpha-CH3-DHT (4) has a higher affinity than 5 alpha-DHT. All other steroids were somewhat less potent than 5 alpha-DHT with F-DHT (2) = I-17 alpha-CH3-DHT (3) greater than or equal to F-NDHT (6) > F-17 alpha-CH3-NDHT (8) = I-DHT (1) greater than or equal to I-NDHT (5) > I-17 alpha-CH3-NDHT (7). The relative biological activity in cells transfected with the androgen receptor and an androgen responsive reporter gene is 4 much greater than 5 alpha-DHT > 2 > 6 > 3 greater than or equal to 1 greater than or equal to 8 greater than or equal to 5 > 7. The iodinated compound, I-17 alpha-CH3-DHT (3), with the highest binding activity was synthesized labeled with I-125 and was shown to bind with high affinity, K-a = 1.9 x 10(10) L/mol, and low nonspecific binding to the androgen receptor in rat prostatic cytosol. However, when radiolabeled [I-125]-17 alpha-CH3-DHT ([I-125]3) was injected into castrated male rats, it showed very poor androgen receptor-mediated uptake into the rat prostate. This was unexpected in light of its superior receptor binding properties and its protection by the 17 alpha-methyl group from metabolic oxidation at C-17. However, the biological potency of I-17 alpha-CH3-DHT (3) was not as high as would have been expected. When I-DHT (1) and I-17 alpha-CH3-DHT (3) were incubated in aqueous media at 37 degrees C they rapidly decomposed, but they were stable at 0 degrees C. The fluorinated analogue 4 treated similarly at 37 degrees C was completely stable. The products of the decomposition reaction of I-DHT (1) at 37 degrees C were identified as iodide and principally 17 beta-hydroxy-5 alpha-androst-7-en-3-one. The temperature dependence of this elimination reaction explains the inconsistency between the high binding to the androgen receptor (measured at 0 degrees C) and the low biological activity, as well as the poor androgen receptor mediated concentration in vivo. The fluorinated analogue F-17 alpha-CH3-DHT (4) has both high affinity for the androgen receptor and high stability in aqueous media. Of the compounds tested, 4 has the highest affinity for the androgen receptor as well as the highest androgenic activity. Thus it is likely that F-17 alpha-CH3-DHT 4 labeled with F-18 will be an excellent receptor-mediated diagnostic imaging agent.
• CH235484
  申请人：——

  公开号：——

  公开（公告）日：——