5-(3-Bromofuran-2-yl)-3-[2-(bromomethyl)-4-chlorophenyl]-1,2,4-oxadiazole | 1186490-09-4

• 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-Bromofuran-2-yl)-3-[2-(bromomethyl)-4-chlorophenyl]-1,2,4-oxadiazole
• CAS: 1186490-09-4
• 化学式: C₁₃H₇Br₂ClN₂O₂
• 分子量: 418.472
• InChiKey: GTKWOKYEWHWNGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3-Bromofuran-2-yl)-3-[2-(bromomethyl)-4-chlorophenyl]-1,2,4-oxadiazole 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 [2-[5-(3-Bromofuran-2-yl)-1,2,4-oxadiazol-3-yl]-5-chlorophenyl]methanol
  参考文献：
  名称：

  Discovery of 3-aryl-5-aryl-1,2,4-oxadiazoles as a new series of apoptosis inducers. 2. Identification of more aqueous soluble analogs as potential anticancer agents

  摘要：

  As a continuation of our efforts to discover and develop the 3-aryl-5-aryl-1,2,4-oxadiazole series of apoptosis inducers as potential anticancer agents, we explored substitutions at the 2-and 3-positions of the 3-aryl group to improve the aqueous solubility properties and identify development candidates. A small substitution such as methyl or hydroxymethyl at the 2-position was well tolerated. This modification, in combination with a 3-substituted furan ring as the 5-aryl group, resulted in 4g and 4h, which have improved solubility properties. Compound 4g was found to have good in vivo efficacy in animal studies via intravenous administration. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.052
• 作为产物：
  描述：

  5-(3-Bromofuran-2-yl)-3-(4-chloro-2-methyl-phenyl)-[1,2,4]oxadiazole 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 溴 作用下， 以 四氯化碳 为溶剂， 生成 5-(3-Bromofuran-2-yl)-3-[2-(bromomethyl)-4-chlorophenyl]-1,2,4-oxadiazole
  参考文献：
  名称：

  Discovery of 3-aryl-5-aryl-1,2,4-oxadiazoles as a new series of apoptosis inducers. 2. Identification of more aqueous soluble analogs as potential anticancer agents

  摘要：

  As a continuation of our efforts to discover and develop the 3-aryl-5-aryl-1,2,4-oxadiazole series of apoptosis inducers as potential anticancer agents, we explored substitutions at the 2-and 3-positions of the 3-aryl group to improve the aqueous solubility properties and identify development candidates. A small substitution such as methyl or hydroxymethyl at the 2-position was well tolerated. This modification, in combination with a 3-substituted furan ring as the 5-aryl group, resulted in 4g and 4h, which have improved solubility properties. Compound 4g was found to have good in vivo efficacy in animal studies via intravenous administration. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.052