5-(3-Chloro-phenyl)-4-cyclohexyl-2-methyl-oxazole | 1027504-33-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(3-Chloro-phenyl)-4-cyclohexyl-2-methyl-oxazole
• 英文别名: 5-(3-Chlorophenyl)-4-cyclohexyl-2-methyl-1,3-oxazole
• CAS: 1027504-33-1
• 化学式: C₁₆H₁₈ClNO
• 分子量: 275.778
• InChiKey: CPVHUVPWJLQHDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(3-Chloro-phenyl)-4-cyclohexyl-2-methyl-oxazole 在 氯磺酸 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 2-Chloro-4-(4-cyclohexyl-2-methyl-oxazol-5-yl)-benzenesulfonyl chloride
  参考文献：
  名称：

  4-(4-Cycloalkyl/aryl-oxazol-5-yl)benzenesulfonamides as Selective Cyclooxygenase-2 Inhibitors:  Enhancement of the Selectivity by Introduction of a Fluorine Atom and Identification of a Potent, Highly Selective, and Orally Active COX-2 Inhibitor JTE-522

  摘要：

  A series of 4-(4-cycloalkyl/aryl-oxazol-5-yl)benzenesulfonamide derivatives were synthesized and evaluated for their abilities to inhibit cyclooxygenase-2 (COX-2) and cyclooxygenase-1 (COX-1) enzymes. In this series, substituent effects at the ortho position to the sulfonamide group on the phenyl ring were examined. Most substituents reduced or lost both COX-2 and COX-1 activities. In contrast, introduction of a fluorine atom preserved COX-2 potency and notably increased COX-1/COX-2 selectivity. This work led to the identification of a potent, highly selective, and orally active COX-2 inhibitor JTE-522 [9d, 4-(4-cyclohexyl-2-methyloxazol-5-yl)2-fluorobenzenesulfonamide], which is currently in phase II clinical trials for the treatment of rheumatoid arthritis, osteoarthritis, and acute pain.

  DOI：

  10.1021/jm010484p
• 作为产物：
  描述：

  [1-(3-Chlorophenyl)-2-cyclohexyl-2-oxoethyl] acetate 在 ammonium acetate 、 溶剂黄146 作用下， 反应 5.0h， 生成 5-(3-Chloro-phenyl)-4-cyclohexyl-2-methyl-oxazole
  参考文献：
  名称：

  4-(4-Cycloalkyl/aryl-oxazol-5-yl)benzenesulfonamides as Selective Cyclooxygenase-2 Inhibitors:  Enhancement of the Selectivity by Introduction of a Fluorine Atom and Identification of a Potent, Highly Selective, and Orally Active COX-2 Inhibitor JTE-522

  摘要：

  A series of 4-(4-cycloalkyl/aryl-oxazol-5-yl)benzenesulfonamide derivatives were synthesized and evaluated for their abilities to inhibit cyclooxygenase-2 (COX-2) and cyclooxygenase-1 (COX-1) enzymes. In this series, substituent effects at the ortho position to the sulfonamide group on the phenyl ring were examined. Most substituents reduced or lost both COX-2 and COX-1 activities. In contrast, introduction of a fluorine atom preserved COX-2 potency and notably increased COX-1/COX-2 selectivity. This work led to the identification of a potent, highly selective, and orally active COX-2 inhibitor JTE-522 [9d, 4-(4-cyclohexyl-2-methyloxazol-5-yl)2-fluorobenzenesulfonamide], which is currently in phase II clinical trials for the treatment of rheumatoid arthritis, osteoarthritis, and acute pain.

  DOI：

  10.1021/jm010484p