17-(3'-thienyl)androsta-5,16-dien-3β-ol | 167948-76-7

• 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: 17-(3'-thienyl)androsta-5,16-dien-3β-ol
• 英文别名: (3β)-17-(thien-3-yl)-androsta-5,16-dien-3-ol；(3β)-17-(3-thienyl)-androsta-5,16-dien-3-ol；(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-thiophen-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 167948-76-7
• 化学式: C₂₃H₃₀OS
• 分子量: 354.557
• InChiKey: JKOYLMZNJPFQNV-RFOVXIPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  17-(3'-thienyl)androsta-5,16-dien-3β-ol 生成 17-(thien-3-yl)-androsta-5,16-dien-3-one
  参考文献：
  名称：

  16 unsaturated C17 heterocyclic steroids useful as steroid C17-20 lyase

  摘要：

  本发明涉及一种作为类固醇C.sub.17-20裂解酶抑制剂有用的.DELTA..sup.16不饱和C.sub.17杂环类固醇。

  公开号：

  US05677293A1
• 作为产物：
  描述：

  去氢表雄酮 在 四(三苯基膦)钯 sodium carbonate 、 一水合肼 、 硫酸肼 作用下， 以 甲醇 、 乙醇 、 水 、 苯 为溶剂， 反应 119.5h， 生成 17-(3'-thienyl)androsta-5,16-dien-3β-ol
  参考文献：
  名称：

  A versatile synthesis of 17-heteroaryl androstenes via palladium-mediated Suzuki cross-coupling with heteroaryl boronic acids

  摘要：

  Suzuki coupling of 17-iodoandrosta-5,16-dien-3 beta-ol (1) and 17-iodoandrosta-4,16-dien-3-one (2) with nine heteroaryl boronic acids (mainly 2- or 3-furanyl, thienyl, benzofuranyl and benzothienyl boronic acid derivatives) were carried out under normal Suzuki condition (Pd(PPh3)(4), 2M Na2CO3 and MeOH), generally yielded C-17-heteroaryl steroids in moderate (10-60%) yields, but furanyl-2- and 5-chlorothienyl-2-boronic acid did not give any coupling product. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.02.004

文献信息

• .increment..sup.16 unsaturated C.sub.17 heterocyclic steroids useful as
  申请人：Merrel Pharmaceuticals, Inc.

  公开号：US05965548A1

  公开（公告）日：1999-10-12

  The present invention relates to .DELTA..sup.16 unsaturated steroids which are useful as steroid C.sub.17-20 lyase inhibitors.

  本发明涉及作为类固醇C.sub.17-20裂解酶抑制剂有用的.DELTA..sup.16不饱和类固醇。
• Inhibition of steroid C17(20) lyase with C-17-heteroaryl steroids
  作者：Joseph P. Burkhart、Cynthia A. Gates、Marie E. Laughlin、Robert J. Resvick、Norton P. Peet

  DOI：10.1016/0968-0896(96)00135-6

  日期：1996.9

  Steroids bearing a heteroaromatic substituent at C-17 were designed as inhibitors of C-17(20) lyase. The thiazoles, furans, and thiophenes appended to the steroid nucleus were positioned on the alpha-face and the beta-face of the steroid, and conjugated with a 16,17-olefin, to test their ability to coordinate the heme iron of the P450 enzyme complex. The position of the heterocycle with respect to the steroid skeleton was determined to be important for optimum affinity and, in general, compounds with the heterocycle attached to a trigonal center at C-17, had the best affinity for C-17(20) lyase. Simple molecular models were used to compare the three types of heterocyclic-substituted steroids. Copyright (C) 1996 Elsevier Science Ltd
• DELTA 16 UNSATURATED C 17 HETEROCYCLIC STEROIDS USEFUL AS STEROID C 17-20 LYASE INHIBITORS
  申请人：MERRELL PHARMACEUTICALS INC.

  公开号：EP0724591A1

  公开（公告）日：1996-08-07
• FLÜSSIGE KÜHLSTOFFZUBEREITUNGEN
  申请人：Symrise AG

  公开号：EP3294262A1

  公开（公告）日：2018-03-21
• ZUBEREITUNGEN MIT CARNOSINEN
  申请人：Symrise AG

  公开号：EP3389619A1

  公开（公告）日：2018-10-24