3-(5-bromo-2-methoxyphenyl)-5-propylisoxazole | 1375103-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(5-bromo-2-methoxyphenyl)-5-propylisoxazole
• 英文别名: 3-(5-bromo-2-methoxyphenyl)-5-n-propylisoxazole；3-(5-Bromo-2-methoxyphenyl)-5-propyl-1,2-oxazole
• CAS: 1375103-00-6
• 化学式: C₁₃H₁₄BrNO₂
• 分子量: 296.164
• InChiKey: VVSHCZGNRSBXNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(5-bromo-2-methoxyphenyl)-5-propylisoxazole 在 三氯化硼 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以64%的产率得到4-bromo-2-(5-propylisoxazol-3-yl)phenol
  参考文献：
  名称：

  Design and synthesis of 4-O-methylhonokiol analogs as inhibitors of cyclooxygenase-2 (COX-2) and PGF1 production

  摘要：

  A series of novel 4-O-methylhonokiol analogs were synthesized in light of revealing structure-activity relationship for inhibitory effect of COX-2 enzyme. The key strategy of the molecular design was oriented towards modification of the potential metabolic soft spots (e. g., phenol and olefin) or by altering the polar surface area via incorporating heterocycles such as isoxazole and triazole. Most of all exhibited the inhibitory effects on COX-2 and PGF(1) production but not macrophage NO production. Especially, aryl carbamates 10 and 11 exhibited more potent inhibitory activity against COX-2 and PGF(1) production. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.028
• 作为产物：
  描述：

  5-溴-2-甲氧基苯甲醛 在 吡啶 、 N-氯代丁二酰亚胺 、 盐酸羟胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 27.0h， 生成 3-(5-bromo-2-methoxyphenyl)-5-propylisoxazole
  参考文献：
  名称：

  Design and synthesis of 4-O-methylhonokiol analogs as inhibitors of cyclooxygenase-2 (COX-2) and PGF1 production

  摘要：

  A series of novel 4-O-methylhonokiol analogs were synthesized in light of revealing structure-activity relationship for inhibitory effect of COX-2 enzyme. The key strategy of the molecular design was oriented towards modification of the potential metabolic soft spots (e. g., phenol and olefin) or by altering the polar surface area via incorporating heterocycles such as isoxazole and triazole. Most of all exhibited the inhibitory effects on COX-2 and PGF(1) production but not macrophage NO production. Especially, aryl carbamates 10 and 11 exhibited more potent inhibitory activity against COX-2 and PGF(1) production. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.028

文献信息

• Synthesis and anti-neuroinflammatory activity of N-heterocyclic analogs based on natural biphenyl-neolignan honokiol
  作者：Yue Yuan、Lalita Subedi、Daesung Lim、Jae-Kyung Jung、Sun Yeou Kim、Seung-Yong Seo

  DOI：10.1016/j.bmcl.2018.11.014

  日期：2019.1

  Novel isoxazole and pyrazole analogs based on natural biphenyl-neolignan honokiol were synthesized and evaluated for their inhibitory activities against nitric oxide production in lipopolysaccharide-activated BV-2 microglial cells. The isoxazole skeleton was constructed via nitrile oxide cycloaddition from oxime 3 and pyrazole was generated by condensation of 4-chromone and alkylhydrazine. Among the analogs, 13b and 14a showed stronger inhibitory activities with IC50 values of 8.9 and 1.2 mu M, respectively, than honokiol.