(E)-16-(4-methylphenyl)methylidene-trans-dehydroandrosterone | 1428382-55-1

• 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: (E)-16-(4-methylphenyl)methylidene-trans-dehydroandrosterone
• 英文别名: (3S,8R,9S,10R,13S,14S,16E)-3-hydroxy-10,13-dimethyl-16-[(4-methylphenyl)methylidene]-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-one
• CAS: 1428382-55-1
• 化学式: C₂₇H₃₄O₂
• 分子量: 390.566
• InChiKey: YMSNYXZYNBOINX-LASSMKGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 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：
  0.59
• 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：

  (E)-16-(4-methylphenyl)methylidene-trans-dehydroandrosterone 、 噻莫西酸 、 苊醌 以 甲醇 为溶剂， 以85%的产率得到
  参考文献：
  名称：

  Synthesis of novel 16-spiro steroids: Spiro-7′-(aryl)tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazolo-trans-androsterone hybrid heterocycles

  摘要：

  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.

  DOI：

  10.1016/j.steroids.2012.12.017
• 作为产物：
  描述：

  去氢表雄酮 、 对甲基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以97%的产率得到(E)-16-(4-methylphenyl)methylidene-trans-dehydroandrosterone
  参考文献：
  名称：

  Synthesis of novel 16-spiro steroids: Spiro-7′-(aryl)tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazolo-trans-androsterone hybrid heterocycles

  摘要：

  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.

  DOI：

  10.1016/j.steroids.2012.12.017

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
• Design, synthesis and biological evaluation of novel steroidal spiro-oxindoles as potent antiproliferative agents
  作者：Bin Yu、Xiao-Jing Shi、Ping-Ping Qi、De-Quan Yu、Hong-Min Liu

  DOI：10.1016/j.jsbmb.2014.01.015

  日期：2014.5

  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.