4-fluoro-N-[[2-(3-methylpyridin-2-yl)-10-oxo-4aH-chromeno[3,2-c]pyridin-3-yl]methyl]benzamide | 1212009-14-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-fluoro-N-[[2-(3-methylpyridin-2-yl)-10-oxo-4aH-chromeno[3,2-c]pyridin-3-yl]methyl]benzamide
• CAS: 1212009-14-7
• 化学式: C₂₆H₂₀FN₃O₃
• 分子量: 441.462
• InChiKey: XRWVCITYQGXMBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-fluoro-N-(prop-2-yn-1-yl)benzamide 、 在 indium(III) triflate 作用下， 以 乙腈 为溶剂， 生成 4-fluoro-N-[[2-(3-methylpyridin-2-yl)-10-oxo-4aH-chromeno[3,2-c]pyridin-3-yl]methyl]benzamide
  参考文献：
  名称：

  Discovery of novel antitubercular 2,10-dihydro-4aH-chromeno[3,2-c]pyridin-3-yl derivatives

  摘要：

  Twenty two novel 2,10-dihydro-4aH-chromeno[3,2-c]pyridin-3-yl derivatives were synthesized by reacting 3-formyl chromone, (sub)-2-amino pyridines, N1-(prop-2-ynyl)arylamides in the presence of indium triflate. The compounds were evaluated their preliminary in-vitro and in-vivo activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB). Among them N-[(4aS)-2-(3-methyl-2-pyridinyl)-10-oxo-2,10-dihydro-4aH-chromeno[3,2-c]pyridin-3-yl]methyl-4-ethylbenzenecarboxamide 4d was found to be the most active compound in-vitro with MIC's of 0.22 and 0.07 mu g/mL against MTB and MDR-TB respectively. In the in-vivo animal model 4d decreased the bacterial load in lung and spleen tissues with 1.11 and 2.94-log10 protections respectively at 25 mg/kg body weight close. (C) 2009 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2009.09.033

文献信息

• Discovery of novel antitubercular 2,10-dihydro-4aH-chromeno[3,2-c]pyridin-3-yl derivatives
  作者：Dharmarajan Sriram、Perumal Yogeeswari、Murugesan Dinakaran、Debjani Banerjee、Pritesh Bhat、Sunil Gadhwal

  DOI：10.1016/j.ejmech.2009.09.033

  日期：2010.1

  Twenty two novel 2,10-dihydro-4aH-chromeno[3,2-c]pyridin-3-yl derivatives were synthesized by reacting 3-formyl chromone, (sub)-2-amino pyridines, N1-(prop-2-ynyl)arylamides in the presence of indium triflate. The compounds were evaluated their preliminary in-vitro and in-vivo activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB). Among them N-[(4aS)-2-(3-methyl-2-pyridinyl)-10-oxo-2,10-dihydro-4aH-chromeno[3,2-c]pyridin-3-yl]methyl-4-ethylbenzenecarboxamide 4d was found to be the most active compound in-vitro with MIC's of 0.22 and 0.07 mu g/mL against MTB and MDR-TB respectively. In the in-vivo animal model 4d decreased the bacterial load in lung and spleen tissues with 1.11 and 2.94-log10 protections respectively at 25 mg/kg body weight close. (C) 2009 Published by Elsevier Masson SAS.