2-[(2E)-3-phenylprop-2-enylidene]cyclopent-4-ene-1,3-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(2E)-3-phenylprop-2-enylidene]cyclopent-4-ene-1,3-dione
• 英文别名: 2-[(E)-3-phenylprop-2-enylidene]cyclopent-4-ene-1,3-dione
• 化学式: C₁₄H₁₀O₂
• 分子量: 210.232
• InChiKey: GUDSEMWIKBPDPM-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  反式肉桂醛 、 4-环戊烯-1,3-二酮 在 titanium(IV)isopropoxide 作用下， 以 四氢呋喃 为溶剂， 反应 12.5h， 以64%的产率得到2-[(2E)-3-phenylprop-2-enylidene]cyclopent-4-ene-1,3-dione
  参考文献：
  名称：

  Synthesis and biological activity of desmethoxy analogues of coruscanone A

  摘要：

  A series of simple desmethoxy analogues of coruscanone A was prepared via a novel version of Ti(iPrO)(4)-mediated Knoevenagel condensation of cyclopentenedione with substituted benzaldehydes and cinnamic aldehydes, and the compounds were evaluated for antifungal activity and cytotoxicity. The most potent 2-benzylidenecyclopent-4-ene-1,3-dione possessed antifungal effect comparable to coruscanone A and a somewhat broader spectrum of activity against Candida species. The compound was also superior to fluconazole against several non-albicans Candida sp. Evaluation of the ability of the compound to influence cell proliferation using two different assays showed that 2-benzylidenecyclopent-4-ene-1,3-dione has lower cytotoxicity compared to the natural product. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.059

文献信息

• Total synthesis of human chymase inhibitor methyllinderone and structure–activity relationships of its derivatives
  作者：Yasunori Aoyama、Toshiro Konoike、Akiko Kanda、Noriyuki Naya、Masatoshi Nakajima

  DOI：10.1016/s0960-894x(01)00265-7

  日期：2001.7

  Total synthesis of human chymase inhibitor methyllinderone has been achieved in only four steps with an overall yield of 21% from dimethyl squarate. We developed an efficient synthetic method for obtaining methyllinderone derivatives and found the active compound. In addition, we propose the inhibition mechanism of the active compound against human chymase using calculations. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis and biological activity of desmethoxy analogues of coruscanone A
  作者：Lucie Tichotová、Eliška Matoušová、Marcel Špulák、Jiří Kuneš、Ivan Votruba、Vladimír Buchta、Milan Pour

  DOI：10.1016/j.bmcl.2011.08.059

  日期：2011.10

  A series of simple desmethoxy analogues of coruscanone A was prepared via a novel version of Ti(iPrO)(4)-mediated Knoevenagel condensation of cyclopentenedione with substituted benzaldehydes and cinnamic aldehydes, and the compounds were evaluated for antifungal activity and cytotoxicity. The most potent 2-benzylidenecyclopent-4-ene-1,3-dione possessed antifungal effect comparable to coruscanone A and a somewhat broader spectrum of activity against Candida species. The compound was also superior to fluconazole against several non-albicans Candida sp. Evaluation of the ability of the compound to influence cell proliferation using two different assays showed that 2-benzylidenecyclopent-4-ene-1,3-dione has lower cytotoxicity compared to the natural product. (C) 2011 Elsevier Ltd. All rights reserved.