(Z)-4-(3-((5-(4-azidophenyl)furan-2-yl)methylene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzoic acid | 1191052-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-4-(3-((5-(4-azidophenyl)furan-2-yl)methylene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzoic acid
• 英文别名: 4-[(3Z)-3-[[5-(4-azidophenyl)furan-2-yl]methylidene]-2-oxo-5-phenylpyrrol-1-yl]benzoic acid
• CAS: 1191052-96-6
• 化学式: C₂₈H₁₈N₄O₄
• 分子量: 474.475
• InChiKey: MXZLZUSDLWXLHK-PGMHBOJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (Z)-4-(3-((5-(4-aminophenyl)furan-2-yl)methylene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzoic acid 在 亚硝酸特丁酯 、 叠氮基三甲基硅烷 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以74%的产率得到(Z)-4-(3-((5-(4-azidophenyl)furan-2-yl)methylene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzoic acid
  参考文献：
  名称：

  Investigation of N-Aryl-3-alkylidenepyrrolinones as Potential Niemann−Pick Type C Disease Therapeutics

  摘要：

  A five-step synthesis of an array of N-aryl-3-alkylidenepyrrolinones, which are potential Niemann-Pick type C (NPC) disease therapeutics, is described. The synthetic route allows for the production of analogues, including photoaffinity and biotinylated derivatives. Compound 1a increased esterification by acyl-coenzyme A:cholesteryl acyltransferase in NPC1 mutant cells. It also decreased LDL uptake and increased cholesterol efflux in both NPC1-deficient and normal cells.

  DOI：

  10.1021/jm900707n

文献信息

• Investigation of <i>N</i>-Aryl-3-alkylidenepyrrolinones as Potential Niemann−Pick Type C Disease Therapeutics
  作者：Casey C. Cosner、John T. Markiewicz、Pauline Bourbon、Christopher J. Mariani、Olaf Wiest、Madalina Rujoi、Anton I. Rosenbaum、Amy Y. Huang、Frederick R. Maxfield、Paul Helquist

  DOI：10.1021/jm900707n

  日期：2009.10.22

  A five-step synthesis of an array of N-aryl-3-alkylidenepyrrolinones, which are potential Niemann-Pick type C (NPC) disease therapeutics, is described. The synthetic route allows for the production of analogues, including photoaffinity and biotinylated derivatives. Compound 1a increased esterification by acyl-coenzyme A:cholesteryl acyltransferase in NPC1 mutant cells. It also decreased LDL uptake and increased cholesterol efflux in both NPC1-deficient and normal cells.