17β-O-acetoxy-4-aza-3-oxo-androst-5-ene | 58636-37-6

• 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: 17β-O-acetoxy-4-aza-3-oxo-androst-5-ene
• 英文别名: 17β-acetoxy-4-aza-androst-5-en-3-one；17β-acetoxy-4-azaandrost-5-en-3-one；17β-Acetoxy-4-aza-androst-5-en-3-on；17beta-Acetoxy-4-aza-androst-5(6)-en-3-one；[(1S,3aS,3bR,9aR,9bS,11aS)-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,6,8,9,9b,10,11-dodecahydroindeno[5,4-f]quinolin-1-yl] acetate
• CAS: 58636-37-6
• 化学式: C₂₀H₂₉NO₃
• 分子量: 331.455
• InChiKey: LVDAYCXZWQPDBZ-SWXUPSNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17β-O-acetoxy-4-aza-3-oxo-androst-5-ene 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 以83%的产率得到3-oxo-4-aza-5-α-androstan-17β-yl acetate
  参考文献：
  名称：

  Crabb, Trevor A.; Ratcliffe, Norman M., Journal of Chemical Research, Miniprint, 1988, # 7, p. 1601 - 1618

  摘要：

  DOI：
• 作为产物：
  描述：

  3-((3S,3aS,5aS,6R,9aS,9bS)-3-acetoxy-3a,6-dimethyl-7-oxododecahydro-1H-cyclopenta[a]naphthalen-6-yl)propanoic acid 以 四氢呋喃 为溶剂， 反应 105.0h， 生成 17β-O-acetoxy-4-aza-3-oxo-androst-5-ene
  参考文献：
  名称：

  Gandhi; Singh; Sachdeva, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 7, p. 539 - 542

  摘要：

  DOI：

文献信息

• Eine neue Methode zur Einf�hrung von Stickstoff in das Steroid-Ringsystem: 17?-O-Acetyl-4-aza-oestradiol
  作者：Milan Uskokovi?、Marcel Gut

  DOI：10.1002/hlca.19590420657

  日期：——

  A novel introduction of nitrogen into the 4 position of some common natural steroids is described.

  描述了将氮引入一些常见的天然类固醇的4位的新方法。
• 4-aza steroids
  申请人：Aventis Pharmaceuticals Inc.

  公开号：US06365597B1

  公开（公告）日：2002-04-02

  The invention related to 4-aza-17&bgr;-(cyclopropoxy)-androst-5&agr;-androstan-3-one, 4-aza-17&bgr;-(cyclopropylamino)-androst-4-en-3-one and related compounds and to compositions incorporating these compounds, as well as the inhibition of C17-20 lyase, 5&agr;-reductase and C17&agr;-hydroxylase and to the use of these compounds in the treatment of androgen and estrogen mediated disorders, including benign prostatic hyperplasia, androgen mediated prostate cancer, estrogen mediated breast cancer and to DHT-mediated disorders such as acne. Disorders relating to the oversynthesis of cortisol, for example, Cushing's Syndrome, are also included. The treatment of androgen-dependent disorders also includes a combination therapy with known androgen-receptor antagonists, such as flutamide. The compounds of the invention have the following general formula:

  该发明涉及4-aza-17β-(环丙氧基)-雄甾-5-烯-3酮，4-aza-17β-(环丙基氨基)-雄甾-4-烯-3酮及其相关化合物，以及包含这些化合物的组合物，还涉及抑制C17-20裂解酶、5α-还原酶和C17α-羟化酶以及在雄激素和雌激素介导的疾病治疗中使用这些化合物，包括良性前列腺增生症、雄激素介导的前列腺癌、雌激素介导的乳腺癌以及DHT介导的疾病，如痤疮。还包括与皮质醇过度合成有关的疾病，例如库欣综合症。雄激素依赖性疾病的治疗还包括与已知的雄激素受体拮抗剂（如氟他胺）的联合治疗。该发明的化合物具有以下通用式：
• 17-BETA-CYCLOPROPYL(AMINO/OXY) 4-AZA STEROIDS AS ACTIVE INHIBITORS OF TESTOSTERONE 5-ALPHA-REDUCTASE AND C17-20-LYASE
  申请人：Aventis Pharmaceuticals Inc.

  公开号：EP0880540B1

  公开（公告）日：2002-06-12
• A microwave promoted and Lewis acid catalysed solventless approach to 4-azasteroids
  作者：Moyurima Borthakur、Romesh C. Boruah

  DOI：10.1016/j.steroids.2008.01.022

  日期：2008.7

  The preparation of 3-oxo-4-azasteroid from A-nor-3,5-secosteroid-3-oic acid is described in a solventless condition catalysed by Lewis acid under microwave irradiation. We utilized urea as an environmentally benign source for the generation of ammonia for the aza cyclization reaction. (C) 2008 Elsevier Inc. All rights reserved.
• Photochemical Reactions. V. [1] Photo-oxidation of 17 β-acetoxy-4-aza-androst-5-en-3-one
  作者：F. Abelló、José Boix、José Gómez、José Morell、Juan-Julio Bonet

  DOI：10.1002/hlca.19750580839

  日期：1975.11.5

  AbstractThe photo‐oxidation of the title compound (1) is described. The isolated products are the result of a [2 + 2] oxygen addition to the olefinic double bond of the enamide.