2-(1-methoxyethylidene)-4-methylcyclopent-4-ene-1,3-dione

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯酯类
• 英文名称: 2-(1-methoxyethylidene)-4-methylcyclopent-4-ene-1,3-dione
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: NWWBYZCVIOMPPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  柠康酸酐 在 三氯化铝 、 potassium carbonate 作用下， 以 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 1.58h， 生成 2-(1-methoxyethylidene)-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

文献信息

• Novel cyclopentenedione antifungal compounds and methods for their use
  申请人：Li Xing-Cong

  公开号：US20050215648A1

  公开（公告）日：2005-09-29

  Compounds and methods useful in the control, treatment, and prevention of fungal activity, of the following formula: where R 1-3 are independently H, alkyl, methyl, acyl, halogen, phenyl, R 4 is H, alkyl, methyl, acyl, alkoxy, halogen, phenyl provided that when R 3 is methyl and R 4 is H, R 1 and R 2 are not both H; and stereoisomers, analogs, and pharmaceutically acceptable salts thereof.

  以下公式的化合物和方法可用于控制、治疗和预防真菌活性，其中R1-3分别为H、烷基、甲基、酰基、卤素、苯基，R4为H、烷基、甲基、酰基、烷氧基、卤素、苯基，但当R3为甲基且R4为H时，R1和R2不能同时为H；其立体异构体、类似物和药学上可接受的盐。
• Cyclopentenedione antifungal compounds and methods for their use
  申请人：The University of Mississippi

  公开号：US07109380B2

  公开（公告）日：2006-09-19

  Compounds and methods useful in the control, treatment, and prevention of fungal activity, of the following formula: where R1-3 are independently H, alkyl, methyl, acyl, halogen, phenyl, R4 is H, alkyl, methyl, acyl, alkoxy, halogen, phenyl provided that when R3 is methyl and R4 is H, R1 and R2 are not both H; and stereoisomers, analogs, and pharmaceutically acceptable salts thereof.

  以下的化合物和方法可用于控制、治疗和预防真菌活性，其化学式如下： 其中R1-3独立地为H、烷基、甲基、酰基、卤素、苯基，R4为H、烷基、甲基、酰基、烷氧基、卤素、苯基，但当R3为甲基且R4为H时，R1和R2不能同时为H；并包括其立体异构体、类似物和药学上可接受的盐。