2-(naphthalene-2-ylmethylene)cyclopent-4-ene-1,3-dione | 1338000-74-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(naphthalene-2-ylmethylene)cyclopent-4-ene-1,3-dione
• 英文别名: 2-(2-Naphthylmethylene)cyclopent-4-ene-1,3-dione；2-(naphthalen-2-ylmethylidene)cyclopent-4-ene-1,3-dione
• CAS: 1338000-74-0
• 化学式: C₁₆H₁₀O₂
• 分子量: 234.254
• InChiKey: XECGLLXCIUPDFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• 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：

  4-环戊烯-1,3-二酮 、 2-萘甲醛 在 titanium(IV)isopropoxide 作用下， 以 四氢呋喃 为溶剂， 反应 12.5h， 以22%的产率得到2-(naphthalene-2-ylmethylene)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

• 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.