Methyl 3-[4-[2-(4-bromophenyl)-1,2-dihydroxyethyl]phenyl]-4,5-dihydro-1,2-oxazole-5-carboxylate | 1027145-75-0

• 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: Methyl 3-[4-[2-(4-bromophenyl)-1,2-dihydroxyethyl]phenyl]-4,5-dihydro-1,2-oxazole-5-carboxylate
• CAS: 1027145-75-0
• 化学式: C₁₉H₁₈BrNO₅
• 分子量: 420.26
• InChiKey: ADKIJTSMKWQZOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  88.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 3-[4-[2-(4-bromophenyl)-1,2-dihydroxyethyl]phenyl]-4,5-dihydro-1,2-oxazole-5-carboxylate 在 碳酸氢钠 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium bromide 作用下， 反应 0.25h， 生成 Methyl 3-[4-[2-(4-bromophenyl)-2-oxoacetyl]phenyl]-4,5-dihydro-1,2-oxazole-5-carboxylate
  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：

  (4-溴苄基)三苯基溴化磷鎓 在 甲酸 、 potassium tert-butylate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 18.5h， 生成 Methyl 3-[4-[2-(4-bromophenyl)-1,2-dihydroxyethyl]phenyl]-4,5-dihydro-1,2-oxazole-5-carboxylate
  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

文献信息

• Development of Potent Non-Carbohydrate Imidazole-Based Small Molecule Selectin Inhibitors with Antiinflammatory Activity
  作者：Deborah H. Slee、Suzanne J. Romano、Jinghua Yu、Truc N. Nguyen、Judy K. John、Neil K. Raheja、Frank U. Axe、Todd K. Jones、William C. Ripka

  DOI：10.1021/jm000508c

  日期：2001.6.1

  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.