(E)-3-(4-{2-[4-((E)-2-Dihexylcarbamoyl-vinyl)-phenyl]-2-oxo-acetyl}-phenyl)-acrylic acid tert-butyl ester | 274904-29-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-3-(4-{2-[4-((E)-2-Dihexylcarbamoyl-vinyl)-phenyl]-2-oxo-acetyl}-phenyl)-acrylic acid tert-butyl ester
• 英文别名: tert-butyl (E)-3-[4-[2-[4-[(E)-3-(dihexylamino)-3-oxoprop-1-enyl]phenyl]-2-oxoacetyl]phenyl]prop-2-enoate
• CAS: 274904-29-9
• 化学式: C₃₆H₄₇NO₅
• 分子量: 573.773
• InChiKey: GMLXEVXGGNYHIA-SIHVKLMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  42
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-{2-[4-((E)-2-Dihexylcarbamoyl-vinyl)-phenyl]-2-oxo-acetyl}-phenyl)-acrylic acid tert-butyl ester 在 ammonium acetate 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (E)-3-(4-{5-[4-((E)-2-Dihexylcarbamoyl-vinyl)-phenyl]-1H-imidazol-4-yl}-phenyl)-acrylic acid
  参考文献：
  名称：

  Development of Potent Non-Carbohydrate Imidazole-Based Small Molecule Selectin Inhibitors with Antiinflammatory Activity

  摘要：

  A novel series of non-carbohydrate imidazole-based selectin inhibitors has been discovered via high-throughput screening using a P-selectin ELISA-based assay system. The initial lead 1 had an IC(50) of 17 muM in the P-selectin ELISA; this potency was significantly improved via an extensive SAR exploration. One of the current lead compounds (29) has an IC(50) of 300 nM in a P-selectin ELISA; it also has good activity in P- and E-selectin cell adhesion assays and shows efficacy in vivo. These compounds represent a novel series of sLe(X) mimetics with antiinflammatory activity. Their unique profile supports our interest in their further evaluation as drug candidates for the treatment of inflammation. Herein we describe the syntheses, optimization, and SAR of this series of novel potent selectin antagonists.

  DOI：

  10.1021/jm000508c
• 作为产物：
  描述：

  二已胺 在 palladium diacetate 、 TEA 、 三(邻甲基苯基)磷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (E)-3-(4-{2-[4-((E)-2-Dihexylcarbamoyl-vinyl)-phenyl]-2-oxo-acetyl}-phenyl)-acrylic acid tert-butyl ester
  参考文献：
  名称：

  Development of Potent Non-Carbohydrate Imidazole-Based Small Molecule Selectin Inhibitors with Antiinflammatory Activity

  摘要：

  A novel series of non-carbohydrate imidazole-based selectin inhibitors has been discovered via high-throughput screening using a P-selectin ELISA-based assay system. The initial lead 1 had an IC(50) of 17 muM in the P-selectin ELISA; this potency was significantly improved via an extensive SAR exploration. One of the current lead compounds (29) has an IC(50) of 300 nM in a P-selectin ELISA; it also has good activity in P- and E-selectin cell adhesion assays and shows efficacy in vivo. These compounds represent a novel series of sLe(X) mimetics with antiinflammatory activity. Their unique profile supports our interest in their further evaluation as drug candidates for the treatment of inflammation. Herein we describe the syntheses, optimization, and SAR of this series of novel potent selectin antagonists.

  DOI：

  10.1021/jm000508c