17β-hydroxy-2-(hydroxymethyl)-17α-pregn-1,4-dien-20-yn-3-one | 60142-08-7

• 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-hydroxy-2-(hydroxymethyl)-17α-pregn-1,4-dien-20-yn-3-one
• 英文别名: 17β-hydroxy-2-(hydroxymethyl)-17α-pregna-1,4-dien-20-yn-3-one；2-Hydroxymethyl-1,2-dehydroethisterone；(8R,9S,10S,13S,14S,17R)-17-ethynyl-17-hydroxy-2-(hydroxymethyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
• CAS: 60142-08-7
• 化学式: C₂₂H₂₈O₃
• 分子量: 340.463
• InChiKey: KVINKXWDTJUXKW-LHZXLZLDSA-N

物化性质

• 沸点：
  508.9±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  达那唑 在 葡萄糖 、 potassium phosphate 、 甘油 、 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 288.0h， 以10.8%的产率得到(2a,17a)-17-羟基-2-(羟基甲基)-孕甾-4-烯-20-炔-3-酮
  参考文献：
  名称：

  Biotransformation of danazol by Fusarium solani and Gibberella fujikuorii, and prolyl endopeptidase inhibition studies of transformed products

  摘要：

  达那唑（17beta-羟基-17\alpha-pregna-2,4-dien-20-yno-[2,3-d] isoxazole）（1）在与 Fusarium solani 发酵时的生物转化产生了 17beta-hydroxy-2-(hydroxymethyl)-17\alpha -pregn-4-en-20-yn-3-one (2) 和 17beta-hydroxy-2-(hydroxymethyl)-17\alpha-pregna-1、4-二烯-20-炔-3-酮（3），而用 Gibberella fujikuorii 发酵 1 只得到化合物 2。 这些化合物的结构是根据现代光谱技术推断出来的。 此外，还研究了达那唑（1）及其转化产物 2 和 3 的脯氨酰内肽酶抑制活性。

  DOI：

  10.3906/kim-0912-400

文献信息

• Compositions comprising ethisterone or its derivatives
  申请人：MULTIMED LIMITED

  公开号：US20020115648A1

  公开（公告）日：2002-08-22

  Treatment of androgen deficiency using a pharmaceutically effective dose of ethisterone or an ethisterone derivative such as danazol. In particular, androgen deficiency in the aging male, also known as the male climateric andropause or the male menopause, can be treated by ethisterone or ethisterone derivatives. Treatment of hypogonadism using ethisterone or ethisterone derivative in combination with testosterone is also effective.

  使用药学上有效剂量的炔雌醇或炔雌醇衍生物（如达那唑）治疗雄激素缺乏症。特别是，炔雌醇或炔雌醇衍生物可治疗衰老男性的雄激素缺乏症，也称为男性气候性更年期或男性更年期。使用炔雌醇或炔雌醇衍生物与睾酮联合治疗性腺功能减退症也很有效。
• Microbial transformation of danazol with Cunninghamella blakesleeana and anti-cancer activity of danazol and its transformed products
  作者：Elias Baydoun、Atia-tul-Wahab、Hina Mehmood、Malik Shoaib Ahmad、Rizwana Malik、Colin Smith、M. Iqbal Choudhary

  DOI：10.1016/j.steroids.2015.11.010

  日期：2016.1

  Biotransformation of danazol (1) (17 beta-hydroxy-17 alpha-pregna-2,4-dien-20-yno-[2,3-d]-isoxazole) with Cunninghamella blakesleeana yielded three new metabolites 2-4 and a known metabolite 5. These metabolites were identified as 14 beta,17 beta-dihydroxy-2-(hydroxymethyl)-17 alpha-pregn-4-en-20-yn-3-one (2), 1 alpha,17 beta-dihydroxy-17 alpha-pregna-2,4-dien-20-yno-[2,3-d]-isoxazole (3), 6 beta,17 beta-dihydroxy-17 alpha-apregna-2,4-dien-20-yno-[2,3-d]-isoxazole (4), and 17 beta-hydroxy-2-(hydroxymethyl)-17 alpha-pregn-1,4-dien-20-yn-3-one (5). Danazol (1) and its derivatives were evaluated against cervical cancer cell line (HeLa). Compound 1 showed a potent cytotoxicity with IC50=0.283 +/- 0.013 mu M, as compared to doxorubicin (IC50=0.506 +/- 0.015 mu M), where compound 3 was also found to be significantly active with IC50 = 13.427 +/- 0.819 mu M. (C) 2015 Elsevier Inc. All rights reserved.
• USE OF DANAZOL IN THE TREATMENT OF HYYPOGONADISM IN MEN
  申请人：Multimed Limited

  公开号：EP1079836B1

  公开（公告）日：2003-10-08
• US6645954B2
  申请人：——

  公开号：US6645954B2

  公开（公告）日：2003-11-11
• Biotransformation of danazol by Fusarium solani and Gibberella fujikuorii, and prolyl endopeptidase inhibition studies of transformed products
  作者：AZIZUDDIN SHAIKH、MUHAMMAD IQBAL CHOUDHARY

  DOI：10.3906/kim-0912-400

  日期：——

  Biotransformation of danazol (17\beta-hydroxy-17\alpha-pregna-2,4-dien-20-yno-[2,3-d] isoxazole) (1) on fermentation with Fusarium solani yielded 17\beta-hydroxy-2-(hydroxymethyl)-17\alpha -pregn-4-en-20-yn-3-one (2) and 17\beta -hydroxy-2-(hydroxymethyl)-17\alpha-pregna-1,4-dien-20-yn-3-one (3), while the fermentation of 1 with Gibberella fujikuorii yielded compound 2 only. The structures of these compounds were deduced on the basis of modern spectroscopic techniques. Prolyl endopeptidase inhibition activities of danazol (1) and its transformed products 2 and 3 are also studied.

  达那唑（17beta-羟基-17\alpha-pregna-2,4-dien-20-yno-[2,3-d] isoxazole）（1）在与 Fusarium solani 发酵时的生物转化产生了 17beta-hydroxy-2-(hydroxymethyl)-17\alpha -pregn-4-en-20-yn-3-one (2) 和 17beta-hydroxy-2-(hydroxymethyl)-17\alpha-pregna-1、4-二烯-20-炔-3-酮（3），而用 Gibberella fujikuorii 发酵 1 只得到化合物 2。 这些化合物的结构是根据现代光谱技术推断出来的。 此外，还研究了达那唑（1）及其转化产物 2 和 3 的脯氨酰内肽酶抑制活性。