16-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)benzylidene]-3β-pyrrolidinoandrost-5-en-17β-ol | 771475-40-2

• 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: 16-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)benzylidene]-3β-pyrrolidinoandrost-5-en-17β-ol
• 英文别名: NSC727090；DPJ-RG-1087；(3S,8R,9S,10R,13S,14S,16E,17S)-16-[[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]methylidene]-10,13-dimethyl-3-pyrrolidin-1-yl-1,2,3,4,7,8,9,11,12,14,15,17-dodecahydrocyclopenta[a]phenanthren-17-ol
• CAS: 771475-40-2
• 化学式: C₃₇H₅₄N₂O₃
• 分子量: 574.847
• InChiKey: MALMVEDFJQSWIS-IPZBAWOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 16-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)benzylidene]-3β-pyrrolidinoandrost-5-en-17β-ol 在 吡啶 作用下， 反应 1.5h， 以70.8%的产率得到NSC728322
  参考文献：
  名称：

  Synthesis of 16E-[3-methoxy-4-(2-aminoethoxy)benzylidene]androstene derivatives as potent cytotoxic agents

  摘要：

  The synthesis and cytotoxic studies of a new series of 16E-arylidene androstene derivatives are reported herein. The impact of incorporating bis-tertiary amino functionalities in the steroid skeleton on cytotoxicity has also been observed. The compounds have been evaluated at National cancer Institute, Bethesda, Maryland, USA for their antineoplastic activity against various tumor cell lines. The synthesized 16E-arylidenosteroids exhibited significant cytotoxicity. Bis-tertiary amino steroid 29 possessing a diethylaminoalkoxy functionality was the most promising compound of the series with a total IP and SC score of 20 in in vivo hollow fiber assay and was selected for further detailed in vivo xenograft testing. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.07.004
• 作为产物：
  描述：

  16-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)benzylidene]-3-pyrrolidino-3,5-androstadien-17-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以75.54%的产率得到16-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)benzylidene]-3β-pyrrolidinoandrost-5-en-17β-ol
  参考文献：
  名称：

  Two androst-5-ene derivatives: 16-[4-(3-chloropropoxy)-3-methoxybenzylidene]-17-oxoandrost-5-en-3β-ol and 16-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)benzylidene]-3β-pyrrolidinoandrost-5-en-17β-ol monohydrate

  摘要：

  In the steroidal nucleus of 16-[4-(3-chloropropoxy)-3-methoxybenzylidene]- 17-oxoandrost-5-en-3beta-ol, C30H29ClO4, (I), the outer two six-membered rings are in chair conformations, while the five-membered ring and the central six-membered ring of the steroidal nucleus adopt half-chair and envelope conformations, respectively. In 16-[3-methoxy-4-(2-pyrrolidin- 1-ylethoxy) benzylidene]-3 beta-pyrrolidinoandrost-5-en- 17 beta-ol monohydrate, C37H54N2O3.H2O, (II), one C atom of one of the outer six-membered rings of the steroid nucleus and the four C atoms of the ethoxypyrrolidine ring are disordered over two sites. The five-membered ring, and the central and one of the outer six-membered rings of the steroidal nucleus exhibit distorted half-chair, chair and envelope conformations, respectively. In (I), intermolecular O - H...O hydrogen bonds link the molecules into chains via a co-operative O - H...O-H...O-H pattern. In (II), intermolecular O - H...O and O-H...N hydrogen bonds link the steroid and water molecules alternately into extended chains.

  DOI：

  10.1107/s0108270103025605

文献信息

• Synthesis of quaternary ammonium salts of 16E-[4-(2-alkylaminoethoxy)-3-methoxybenzylidene]androstene derivatives as skeletal muscle relaxants
  作者：Ranju Bansal、Sheetal Guleria、Louise C. Young、Alan L. Harvey

  DOI：10.1016/j.steroids.2010.11.006

  日期：2011.2

  Synthesis of eighteen new quaternary ammonium salts of 16E-arylidene androstene derivatives as skeletal muscle relaxants is reported in the present study. The effects of possibly extended interonium distances on muscle relaxant activity are discussed. All the quaternary ammonium steroids produced reduction in the twitch responses, when screened for in vitro neuromuscular blocking activity using isolated chick biventer cervicis muscle preparation. However, the variable interonium distance, which is believed to range from 11 to 17 angstrom in these quaternary compounds and is associated with the built in flexibility of these structures about the single bonds on the moieties linked to ring D of the steroid skeleton, resulted in varied degrees of muscle relaxant activity. Some of the compounds also inhibited acetylcholinesterase activity in low concentrations so that they would not be directly suitable for use as muscle relaxants. (C) 2010 Elsevier Inc. All rights reserved.