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 | 1191052-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: 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
• CAS: 1191052-99-9
• 化学式: C₄₉H₅₃BrN₈O₈S
• 分子量: 993.979
• InChiKey: JECNCQXQGUDTMB-BPZJDTPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  67
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  217
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为产物：
  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

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.