3β-hydroxy-16-p-chlorobenzylidene-5α-androstan-17-one | 303128-79-2

• 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: 3β-hydroxy-16-p-chlorobenzylidene-5α-androstan-17-one
• 英文别名: 16-(4-chloro-benzylidene)-5α-androstan-3β-ol-17-one；(3S,5S,8R,9S,10S,13S,14S,16E)-16-[(4-chlorophenyl)methylidene]-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-one
• CAS: 303128-79-2
• 化学式: C₂₆H₃₃ClO₂
• 分子量: 413.0
• InChiKey: IFHFLNDFNOCYGD-GXDGBQPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 重原子数：
  29.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-16-p-chlorobenzylidene-5α-androstan-17-one 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 Jones reagent 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 11.0h， 生成 16-(4-chloro-benzylidene)-3β-pyrrolidino-5α-androstan-17β-yl acetate
  参考文献：
  名称：

  Synthesis, characterization and biological evaluation of some 16E-arylidene androstane derivatives as potential anticancer agents

  摘要：

  A series of new 16E-arylidene androstane derivatives were synthesized and characterized. The new compounds were screened for their anticancer activities against the human cancer cell lines SW480, A549, HepG2 and HeLa in vitro using the MTT assay. The results of the in vitro study showed that a number of compounds have shown IC(50) values lower than 20 mu M against the four cancer cell lines. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.03.015
• 作为产物：
  描述：

  醋酸去氢表雄酮 生成 3β-hydroxy-16-p-chlorobenzylidene-5α-androstan-17-one
  参考文献：
  名称：

  CHAGONDA, LAMECK S.;MARPLES, BRIAN A., J. CHEM. SOC. PERKIN TRANS.,(1988) N 4, 875-879

  摘要：

  DOI：

文献信息

• Stereoselective Synthesis of Novel Dispiro Oxindole-pyrrolothiazole-androsterone Hybrids
  作者：Selvaraj Kanchithalaivan、Mani Anusha Rani、Raju Ranjith Kumar

  DOI：10.1080/00397911.2014.928729

  日期：2014.11.2

  Abstract A facile synthesis of novel dispiro oxindole-pyrrolothiazole-androsterone hybrid heterocycles has been achieved through 1,3-dipolar cycloaddition. The reaction proceeds stereo- and regioselectively, affording a single isomer of the product in excellent yields with the formation of two C–C and one C–N bonds and creation of four new contiguous stereocenters in one step. GRAPHICAL ABSTRACT

  摘要 通过 1,3-偶极环加成实现了新型二螺羟吲哚-吡咯并噻唑-雄酮杂环化合物的简便合成。该反应以立体选择性和区域选择性进行，以极好的收率提供产物的单一异构体，同时形成两个 C-C 键和一个 C-N 键，并一步产生四个新的连续立体中心。图形概要
• Chagonda, Lameck S.; Marples, Brian A., Journal of the Chemical Society. Perkin transactions I, 1988, p. 875 - 880
  作者：Chagonda, Lameck S.、Marples, Brian A.

  DOI：——

  日期：——
• Synthesis of novel 16-spiro steroids: Spiro-7′-(aryl)tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazolo-trans-androsterone hybrid heterocycles
  作者：Selvaraj Kanchithalaivan、Raju Ranjith Kumar、Subbu Perumal

  DOI：10.1016/j.steroids.2012.12.017

  日期：2013.4

  The 1,3-dipolar cycloaddition of azomethine ylide derived in situ from the reaction of acenaphthylene-1,2-dione and 1,3-thiazolane-4-carboxylic acid to various exocyclic dipolarophiles synthesized from trans-androsterone and trans-dehydroandrosterone afforded a library of novel spiro[5'.2 '']acenaphthylene-1 ''-one-spiro[16.6']-(7'-aryl)-tetrahydro-1H-pyrrolo [1,2-c][1,3]thiazolo-trans-androsterone/dehydroandrosterone hybrid heterocycles respectively. These reactions proceeded stereo-specifically affording a single isomer of the 16-spiro steroids in excellent yields. (C) 2013 Elsevier Inc. All rights reserved.