6-(benzylcarbamoyl)-2-(5-nitrofuran-2-carboxamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide | 1580443-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 6-(benzylcarbamoyl)-2-(5-nitrofuran-2-carboxamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide
• 英文别名: 6-N-benzyl-2-[(5-nitrofuran-2-carbonyl)amino]-5,7-dihydro-4H-thieno[2,3-c]pyridine-3,6-dicarboxamide
• CAS: 1580443-15-7
• 化学式: C₂₁H₁₉N₅O₆S
• 分子量: 469.478
• InChiKey: MMFJFDQNAMTJKI-UHFFFAOYSA-N

物化性质

• 沸点：
  623.6±55.0 °C(predicted)
• 密度：
  1.515±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  192
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-硝基-2-糠酸 在 草酰氯 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 6-(benzylcarbamoyl)-2-(5-nitrofuran-2-carboxamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide
  参考文献：
  名称：

  Development of novel tetrahydrothieno[2,3-c]pyridine-3-carboxamide based Mycobacterium tuberculosis pantothenate synthetase inhibitors: Molecular hybridization from known antimycobacterial leads

  摘要：

  Twenty six 2,6-disubstituted 4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide derivatives were designed by molecular hybridization approach using and synthesized from piperidin-4-one by five step synthesis. Compounds were evaluated for Mycobacterium tuberculosis (MTB) pantothenate synthetase (PS) inhibition study, in vitro activities against MTB, cytotoxicity against RAW 264.7 cell line. Among the compounds, 6-(4-nitrophenylsulfonyl)-2-(5-nitrothiophene-2-carboxamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide (11) was found to be the most active compound with IC50 of 5.87 +/- 0.12 mu M against MTB PS, inhibited MTB with MIC of 9.28 mu M and it was non-cytotoxic at 50 mu M. The binding affinity of the most potent inhibitor 11 was further confirmed biophysically through differential scanning fluorimetry. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.030

文献信息

• Development of novel tetrahydrothieno[2,3-c]pyridine-3-carboxamide based Mycobacterium tuberculosis pantothenate synthetase inhibitors: Molecular hybridization from known antimycobacterial leads
  作者：Ganesh Samala、Parthiban Brindha Devi、Radhika Nallangi、Jonnalagadda Padma Sridevi、Shalini Saxena、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmc.2014.01.030

  日期：2014.3

  Twenty six 2,6-disubstituted 4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide derivatives were designed by molecular hybridization approach using and synthesized from piperidin-4-one by five step synthesis. Compounds were evaluated for Mycobacterium tuberculosis (MTB) pantothenate synthetase (PS) inhibition study, in vitro activities against MTB, cytotoxicity against RAW 264.7 cell line. Among the compounds, 6-(4-nitrophenylsulfonyl)-2-(5-nitrothiophene-2-carboxamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide (11) was found to be the most active compound with IC50 of 5.87 +/- 0.12 mu M against MTB PS, inhibited MTB with MIC of 9.28 mu M and it was non-cytotoxic at 50 mu M. The binding affinity of the most potent inhibitor 11 was further confirmed biophysically through differential scanning fluorimetry. (C) 2014 Elsevier Ltd. All rights reserved.