2-[(E)-1-hydroxy-3-(thiophen-2-yl)allylidene]-4-methylcyclopent-4-ene-1,3-dione | 923025-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(E)-1-hydroxy-3-(thiophen-2-yl)allylidene]-4-methylcyclopent-4-ene-1,3-dione
• CAS: 923025-78-9
• 化学式: C₁₃H₁₀O₃S
• 分子量: 246.287
• InChiKey: ORVBQHHHWLSBQK-ZXXRXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-[(E)-1-hydroxy-3-(thiophen-2-yl)allylidene]-4-methylcyclopent-4-ene-1,3-dione 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.08h， 生成 2-[(E)-1-methoxy-3-(thiophen-2-yl)allylidene]-4-methylcyclopent-4-ene-1,3-dione
  参考文献：
  名称：

  Synthesis, Antifungal Activity, and Structure−Activity Relationships of Coruscanone A Analogues

  摘要：

  Coruscanone A, a plant-derived cyclopentenedione derivative, showed potent in vitro antifungal activity against Candida albicans and Cryptococcus neoformans comparable to amphotericin B and fluconazole. A series of analogues have been synthesized by modification of the cyclopentenedione ring, the enolic methoxy functionality, and the side chain styryl moiety of this natural product lead. A structurally close 1,4-benzoquinone analogue was also prepared. All the compounds were examined for their in vitro activity against major opportunistic fungal pathogens including C. albicans, C. neoformans, and Aspergillus fumigatus and fluconazole-resistant C. albicans strains, with several analogues demonstrating potent antifungal activity. Structure-activity relationship studies indicate that the 2-methoxymethylenecyclopent-4-ene-1,3-dione structural moiety is the pharmacophore responsible for the antifungal activity of this class of compounds while the side chain styryl-like moiety plays an important complementary role, presumably contributing to target binding.

  DOI：

  10.1021/jm061123i
• 作为产物：
  描述：

  [2-oxo-4-(thiophen-2-yl)-(3E)-butenyl]triphenylphosphonium bromide 在 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 、 苯 为溶剂， 生成 2-[(E)-1-hydroxy-3-(thiophen-2-yl)allylidene]-4-methylcyclopent-4-ene-1,3-dione
  参考文献：
  名称：

  Synthesis, Antifungal Activity, and Structure−Activity Relationships of Coruscanone A Analogues

  摘要：

  Coruscanone A, a plant-derived cyclopentenedione derivative, showed potent in vitro antifungal activity against Candida albicans and Cryptococcus neoformans comparable to amphotericin B and fluconazole. A series of analogues have been synthesized by modification of the cyclopentenedione ring, the enolic methoxy functionality, and the side chain styryl moiety of this natural product lead. A structurally close 1,4-benzoquinone analogue was also prepared. All the compounds were examined for their in vitro activity against major opportunistic fungal pathogens including C. albicans, C. neoformans, and Aspergillus fumigatus and fluconazole-resistant C. albicans strains, with several analogues demonstrating potent antifungal activity. Structure-activity relationship studies indicate that the 2-methoxymethylenecyclopent-4-ene-1,3-dione structural moiety is the pharmacophore responsible for the antifungal activity of this class of compounds while the side chain styryl-like moiety plays an important complementary role, presumably contributing to target binding.

  DOI：

  10.1021/jm061123i