3-(3-溴苯基)-5-(氯甲基)-1,2,4-恶二唑 | 848316-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(3-溴苯基)-5-(氯甲基)-1,2,4-恶二唑
• 英文名称: 3-(3-bromophenyl)-5-(chloromethyl)-1,2,4-oxadiazole
• CAS: 848316-20-1
• 化学式: C₉H₆BrClN₂O
• mdl: MFCD07330270
• 分子量: 273.516
• InChiKey: KCMRCFPJJKBQEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  对羟基苯丙酸甲酯 、 3-(3-溴苯基)-5-(氯甲基)-1,2,4-恶二唑 在 水 、 caesium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 3-(4-((3-(3-bromophenyl)-1,2,4-oxadiazol-5-yl)methoxy)phenyl)propanoic acid
  参考文献：
  名称：

  Phenoxymethyl 1,3-oxazoles and 1,2,4-oxadiazoles as potent and selective agonists of free fatty acid receptor 1 (GPR40)

  摘要：

  A screening hit that showed a weak (EC50 = 18 mu M), partial agonistic effect on GPR40 was used a prototype for expedited hit expansion effort using a set of advanced building blocks. The latter yielded several 1,3-oxazoles and 1,2,4-oxadiazoles with significantly improved potency (best EC50 = 0.058 mu M). The lead compounds in each chemotype showed a very good ADME profile (aqueous solubility, plasma protein binding, microsomal stability and membrane permeability) and no appreciable inhibition of key cytochromes P450. The compounds reported are significant new starting points for further preclinical development of future diabetic agents with a mechanism of action for which a first-in-class agent is yet to be approved. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.018

文献信息

• Phenoxymethyl 1,3-oxazoles and 1,2,4-oxadiazoles as potent and selective agonists of free fatty acid receptor 1 (GPR40)
  作者：Ihor Zahanich、Ivan Kondratov、Vasyl Naumchyk、Yuri Kheylik、Maxim Platonov、Sergey Zozulya、Mikhail Krasavin

  DOI：10.1016/j.bmcl.2015.06.018

  日期：2015.8

  A screening hit that showed a weak (EC50 = 18 mu M), partial agonistic effect on GPR40 was used a prototype for expedited hit expansion effort using a set of advanced building blocks. The latter yielded several 1,3-oxazoles and 1,2,4-oxadiazoles with significantly improved potency (best EC50 = 0.058 mu M). The lead compounds in each chemotype showed a very good ADME profile (aqueous solubility, plasma protein binding, microsomal stability and membrane permeability) and no appreciable inhibition of key cytochromes P450. The compounds reported are significant new starting points for further preclinical development of future diabetic agents with a mechanism of action for which a first-in-class agent is yet to be approved. (C) 2015 Elsevier Ltd. All rights reserved.