(E)-16-(4-fluorophenyl)methylidene-trans-dehydroandrosterone | 1428382-54-0

• 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: (E)-16-(4-fluorophenyl)methylidene-trans-dehydroandrosterone
• 英文别名: 16-((E)-4-fluorobenzylidene)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one；(3S,8R,9S,10R,13S,14S,16E)-16-[(4-fluorophenyl)methylidene]-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-one
• CAS: 1428382-54-0
• 化学式: C₂₆H₃₁FO₂
• 分子量: 394.529
• InChiKey: ZEZJMEPOMUWRBS-MOLOORIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-16-(4-fluorophenyl)methylidene-trans-dehydroandrosterone 、 靛红 、 噻莫西酸 以 甲醇 为溶剂， 以89%的产率得到spiro[5′.3″]oxindole-spiro[6′.16]-7′-(4-fluorophenyl)-tetrahydro-1H-pyrrolo[1′,2′-c][1′,3′] thiazolo-trans-dehydroandrosterone
  参考文献：
  名称：

  立体选择性合成新型二螺羟吲哚-吡咯并噻唑-雄酮杂化物

  摘要：

  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

  DOI：

  10.1080/00397911.2014.928729
• 作为产物：
  描述：

  去氢表雄酮 、 对氟苯甲醛 在 potassium fluoride on basic alumina 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (E)-16-(4-fluorophenyl)methylidene-trans-dehydroandrosterone
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel steroidal spiro-oxindoles as potent antiproliferative agents

  摘要：

  Two series of novel steroidal spiro-pyrrolidinyl oxindoles 3a-t and 6a-c were designed and synthesized from dehydroepiandrosterone using the 1,3-dipolar cycloaddition as the key step and further evaluated for their antiproliferative activities for four human cancer cell lines (MGC-803, EC109, SMMC-7721 and MCF-7). This protocol achieved the formation of two C-C bonds, one C-N bond and the creation of one new five-membered pyrrolidine ring and three contiguous stereocenters in a single operation. Biological evaluation showed that these synthesized steroidal spiro-pyrrolidinyl oxindoles possessed moderate to good antiproliferative activities against the tested cell lines and some of them were more potent than 5-Fu. Particularly, compound 3g showed good antiproliferative activity against SMMC-7721 (IC50= 0.71 mu M). Steroid dimer 6b showed improved antiproliferative activities against SMMC-7721 and MCF-7 with the IC50 values of 4.30 and 2.06 mu M, respectively. Flow cytometry analysis demonstrated that compound 3n caused the cellular early apoptosis and cell cycle arrest at G2/M phase in a concentration- and time-independent manner. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.jsbmb.2014.01.015

文献信息

• 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.