(E)-1-bromo-4-[4-(tert-butyldimethylsilyloxy)phenyl]but-3-en-2-one | 923025-57-4

• 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: (E)-1-bromo-4-[4-(tert-butyldimethylsilyloxy)phenyl]but-3-en-2-one
• 英文别名: (E)-1-bromo-4-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]but-3-en-2-one
• CAS: 923025-57-4
• 化学式: C₁₆H₂₃BrO₂Si
• 分子量: 355.347
• InChiKey: XQUAPHVVSFAMNZ-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-bromo-4-[4-(tert-butyldimethylsilyloxy)phenyl]but-3-en-2-one 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 生成 (5E)-5-[(E)-4-(tert-butyldimethylsilyloxyphenyl)-2-oxobut-3-enylidene]-3-methylfuran-2(5H)-one
  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：

  (3E)-4-{4-[(tert-butyldimethylsilyl)oxy]phenyl}but-3-en-2-one 在 pyrrolidone hydrotribromide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以65%的产率得到(E)-1-bromo-4-[4-(tert-butyldimethylsilyloxy)phenyl]but-3-en-2-one
  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

• Synthesis, Antifungal Activity, and Structure−Activity Relationships of Coruscanone A Analogues
  作者：K. Suresh Babu、Xing-Cong Li、Melissa R. Jacob、Qifeng Zhang、Shabana I. Khan、Daneel Ferreira、Alice M. Clark

  DOI：10.1021/jm061123i

  日期：2006.12.1

  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.