(5E)-3-methyl-5-[(E)-2-oxo-4-phenylbut-3-enylidene]furan-2(5H)-one | 923025-66-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (5E)-3-methyl-5-[(E)-2-oxo-4-phenylbut-3-enylidene]furan-2(5H)-one
• 英文别名: (E)-4-cinnamoylmethylidene-2-methylbut-2-en-4-olide；E-4-cinnamoylmethylidene-2-methylbut-2-en-4-olide；(5E)-3-methyl-5-[(E)-2-oxo-4-phenylbut-3-enylidene]furan-2-one
• CAS: 923025-66-5
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: VKFRFAVWANZOQG-ACLLVWJRSA-N

物化性质

• 熔点：
  158-159 °C(Solv: chloroform (67-66-3); ethanol (64-17-5))
• 沸点：
  407.7±45.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5E)-3-methyl-5-[(E)-2-oxo-4-phenylbut-3-enylidene]furan-2(5H)-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以62%的产率得到2-[(E)-1-hydroxy-3-phenylallylidene]-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：

  (E)-1-bromo-4-phenylbut-3-en-2-one 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 8.0h， 生成 (5E)-3-methyl-5-[(E)-2-oxo-4-phenylbut-3-enylidene]furan-2(5H)-one
  参考文献：
  名称：

  Antifungal Cyclopentenediones from Piper coruscans

  摘要：

  Coruscanones A and B, two new antifungal cyclopentenedione derivatives, have been isolated from Piper coruscans and their structures elucidated by spectroscopic and chemical methods. Coruscanone A exhibits significant antifungal activity against Candida albicans and its azole-resistant strains and may serve as a template for a new class of antifungal agents.

  DOI：

  10.1021/ja048081c

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.

  在控制、治疗和预防真菌活性方面有用的化合物和方法，具有以下化学式：其中R1-3独立地是H、烷基、甲基、酰基、卤素、苯基，R4是H、烷基、甲基、酰基、烷氧基、卤素、苯基，但当R3是甲基且R4是H时，R1和R2不同时为H；以及其立体异构体、类似物和药用可接受的盐。
• NOVEL CYCLOPENTENEDIONE ANTIFUNGAL COMPOUNDS AND METHODS FOR THEIR USE
  申请人：THE UNIVERSITY OF MISSISSIPPI

  公开号：EP1730095A2

  公开（公告）日：2006-12-13
• EP1730095A4
  申请人：——

  公开号：EP1730095A4

  公开（公告）日：2008-04-02
• US7109380B2
  申请人：——

  公开号：US7109380B2

  公开（公告）日：2006-09-19
• [EN] NOVEL CYCLOPENTENEDIONE ANTIFUNGAL COMPOUNDS AND METHODS FOR THEIR USE<br/>[FR] NOUVEAUX COMPOSES CYCLOPENTENEDIONE ANTIFONGIQUES ET TECHNIQUES D'UTILISATION DE CEUX-CI
  申请人：UNIV MISSISSIPPI

  公开号：WO2005091754A2

  公开（公告）日：2005-10-06

  Novel compounds and methods useful in the control, treatment, and prevention of fungal activity.