(Z)-N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-4-(3-((5-(4-bromophenyl)furan-2-yl)methylene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzamide | 1191052-87-5

• 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)-N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-4-(3-((5-(4-bromophenyl)furan-2-yl)methylene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzamide
• 英文别名: N-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl]-4-[(3Z)-3-[[5-(4-bromophenyl)furan-2-yl]methylidene]-2-oxo-5-phenylpyrrol-1-yl]benzamide
• CAS: 1191052-87-5
• 化学式: C₃₆H₃₄BrN₅O₆
• 分子量: 712.6
• InChiKey: QNLDHPOCKIHLRV-OLFWJLLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-炔丙基生物素酰胺 、 (Z)-N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-4-(3-((5-(4-bromophenyl)furan-2-yl)methylene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzamide 在 sodium ascorbate 、 copper(II) sulfate 作用下， 以 水 、 丙酮 为溶剂， 以73%的产率得到N-[2-[2-[2-[2-[4-[[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]methyl]triazol-1-yl]ethoxy]ethoxy]ethoxy]ethyl]-4-[(3Z)-3-[[5-(4-bromophenyl)furan-2-yl]methylidene]-2-oxo-5-phenylpyrrol-1-yl]benzamide
  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
• 作为产物：
  描述：

  (Z)-4-(3-((5-(4-bromophenyl)furan-2-yl)methylene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzoic acid 、 1-氨基-11-叠氮-3,6,9-三氧杂十一烷 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 吡啶 为溶剂， 以65%的产率得到(Z)-N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-4-(3-((5-(4-bromophenyl)furan-2-yl)methylene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzamide
  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.