2-(benzo[d]isoxazol-3-yl)-N-(pyridin-3-ylmethyl)acetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并异恶唑
• 英文名称: 2-(benzo[d]isoxazol-3-yl)-N-(pyridin-3-ylmethyl)acetamide
• 英文别名: 2-(1,2-benzoxazol-3-yl)-N-(pyridin-3-ylmethyl)acetamide
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: LASSBTXSBLDOMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2'-羟基苯乙酮 在 盐酸羟胺 、 sodium 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.17h， 生成 2-(benzo[d]isoxazol-3-yl)-N-(pyridin-3-ylmethyl)acetamide
  参考文献：
  名称：

  1,2-Benzisoxazole-3-acetamide derivatives as dual agents for DPP-IV inhibition and anticancer activity

  摘要：

  Herein, we have designed various benzisoxazole acetamide derivatives with and without glycine spacer as DPP-IV inhibitors. Compounds 9a-d and 11a-e were synthesized and screened for their in vitro DPP-IV inhibition. Compounds 11a and 11c showed moderate activity for DPP-IV inhibition, whereas other remained inactive at 25-200 mu M concentrations. DPP-IV inhibition can be a good strategy for modulating diabetes and cancer; hence, we have screened compounds 9a-d and 11a-e for their anticancer activity using MTT assay against A549 and MCF7 cell lines. Compounds 9a-d without glycine spacer have shown good anticancer activity compared to compounds 11a-e with glycine spacer. Compound 9b has shown moderate activity with IC50 values 4.72 +/- 0.72 and 4.39 +/- 0.809 mu M against A549 and MCF7 cell lines, respectively. Interestingly, compound 9c with cyano group has shown very good anticancer activity with IC50 2.36 +/- 0.34 mu M against MCF7 cell line as compared to fluorouracil with IC50 45.04 +/- 1.02 mu M.[GRAPHICS].

  DOI：

  10.1080/00397911.2018.1508723

文献信息

• 1,2-Benzisoxazole-3-acetamide derivatives as dual agents for DPP-IV inhibition and anticancer activity
  作者：Shubhendu Karandikar、Rina Soni、Shubhangi S. Soman、Shweta Umar、Balakrishnan Suresh

  DOI：10.1080/00397911.2018.1508723

  日期：2018.11.17

  Herein, we have designed various benzisoxazole acetamide derivatives with and without glycine spacer as DPP-IV inhibitors. Compounds 9a-d and 11a-e were synthesized and screened for their in vitro DPP-IV inhibition. Compounds 11a and 11c showed moderate activity for DPP-IV inhibition, whereas other remained inactive at 25-200 mu M concentrations. DPP-IV inhibition can be a good strategy for modulating diabetes and cancer; hence, we have screened compounds 9a-d and 11a-e for their anticancer activity using MTT assay against A549 and MCF7 cell lines. Compounds 9a-d without glycine spacer have shown good anticancer activity compared to compounds 11a-e with glycine spacer. Compound 9b has shown moderate activity with IC50 values 4.72 +/- 0.72 and 4.39 +/- 0.809 mu M against A549 and MCF7 cell lines, respectively. Interestingly, compound 9c with cyano group has shown very good anticancer activity with IC50 2.36 +/- 0.34 mu M against MCF7 cell line as compared to fluorouracil with IC50 45.04 +/- 1.02 mu M.[GRAPHICS].