(Z)-4-(3-((5-(4-bromophenyl)furan-2-yl)methylene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzoic acid | 1191052-37-5

• 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)-4-(3-((5-(4-bromophenyl)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-bromophenyl)furan-2-yl]methylidene]-2-oxo-5-phenylpyrrol-1-yl]benzoic acid
• CAS: 1191052-37-5
• 化学式: C₂₈H₁₈BrNO₄
• 分子量: 512.359
• InChiKey: PTNVXMRZJRXBHR-PGMHBOJBSA-N

物化性质

• 熔点：
  >200 °C
• 沸点：
  740.9±60.0 °C(Predicted)
• 密度：
  1.504±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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 在 copper(l) iodide 、 sodium azide 、 sodium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 二甲基亚砜 为溶剂， 以83%的产率得到(Z)-4-(3-((5-(4-aminophenyl)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
• 作为产物：
  描述：

  (Z)-methyl 4-(3-((5-(4-bromophenyl)furan-2-yl)methylene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzoate 在 lithium iodide 作用下， 以 吡啶 为溶剂， 以95%的产率得到(Z)-4-(3-((5-(4-bromophenyl)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

• Identification of active-site inhibitors of glycosyltransferases using a generalizable high-throughput screen
  申请人：Kahne Walker Suzanne

  公开号：US20050142629A1

  公开（公告）日：2005-06-30

  A method is described for identifying a compound that modulates the ability of a glycosyltransferase to bind a substrate comprising combining a glycosyltransferase, a labeled substrate, and a compound, in a reaction vessel, under conditions known to be suitable for the glycosyltransferase to bind the labeled substrate, measuring an amount of labeled substrate bound to the glycosyltransferase, and comparing the amount to a standardized amount to identify a relative increase or decrease in substrate bound glycosyltransferase, thereby identifying a compound that modulates the ability of the glycosyltransferase to bind the substrate. A composition comprising an effective amount of a compound of Formula I (the substituents of which are described herein), or a stereoisomer, or pharmaceutically acceptable salt thereof, that inhibits the ability of a glycosyltransferase to bind a substrate, in a pharmaceutically acceptable carrier is provided
• US7344850B2
  申请人：——

  公开号：US7344850B2

  公开（公告）日：2008-03-18
• 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.