16-[3-methoxy-4-{2-(piperidin-1-yl)ethoxy}-benzylidene]-17-oxo-5-androsten-3β-ol | 500899-66-1

• 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-(piperidin-1-yl)ethoxy}-benzylidene]-17-oxo-5-androsten-3β-ol
• 英文别名: 16-[3-methoxy-4-(2-piperidin-1-ylethoxy)benzylidene]-17-oxo-5-androsten-3β-ol；DPJ-RG-1071；NSC727078；(3S,8R,9S,10R,13S,14S,16E)-3-hydroxy-16-[[3-methoxy-4-(2-piperidin-1-ylethoxy)phenyl]methylidene]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-one
• CAS: 500899-66-1
• 化学式: C₃₄H₄₇NO₄
• 分子量: 533.751
• InChiKey: LZVXXIKQRFYDKB-BCFXJNIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  16-[3-methoxy-4-{2-(piperidin-1-yl)ethoxy}-benzylidene]-17-oxo-5-androsten-3β-ol 在 环己酮 、 aluminum isopropoxide 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以100%的产率得到16-[3-methoxy-4-{2-(piperidin-1-yl)ethoxy}-benzylidene]-4-androstene-3,17-dione
  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：

  去氢表雄酮 、 3-甲氧基-4-[2-(1-哌啶基)乙氧基]苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以97.3%的产率得到16-[3-methoxy-4-{2-(piperidin-1-yl)ethoxy}-benzylidene]-17-oxo-5-androsten-3β-ol
  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

文献信息

• 16-[3-Methoxy-4-(2-piperidin-1-ylethoxy)benzylidene]-17-oxoandrost-5-en-3β-yl acetate monohydrate
  作者：S. Thamotharan、V. Parthasarathi、Ranju Gupta、Sheetal Guleria、D. P. Jindal、Anthony Linden

  DOI：10.1107/s010827010202005x

  日期：2002.12.15

  The title compound, C36H49NO5.H2O, has the outer two six-membered rings of the steroid nucleus in chair conformations. The central ring B of the steroid nucleus is in an 8beta,9alpha-half-chair conformation, while ring D of the steroid adopts a slightly distorted 13beta,14alpha-half-chair conformation. The piperidine ring is in a chair conformation. The methoxybenzylidene moiety has an E configuration with respect to the carbonyl group at position 17. Intermolecular O-H...O and O-H...N hydrogen bonds link the steroid and water molecules into chains which run parallel to the b axis.