4-(5-bromothiophene-2-carboxamido)-N-(5-(3-(dimethylamino) propylcarbamoyl)-1-methyl-1H-pyrrol-3-yl)-1-methyl-1H-pyrrole-2-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 4-(5-bromothiophene-2-carboxamido)-N-(5-(3-(dimethylamino) propylcarbamoyl)-1-methyl-1H-pyrrol-3-yl)-1-methyl-1H-pyrrole-2-carboxamide
• 英文别名: 4-[(5-bromothiophene-2-carbonyl)amino]-N-[5-[3-(dimethylamino)propylcarbamoyl]-1-methylpyrrol-3-yl]-1-methylpyrrole-2-carboxamide
• 化学式: C₂₂H₂₇BrN₆O₃S
• 分子量: 535.465
• InChiKey: QSIXQWWPXILGRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-噻吩硼酸 、 4-(5-bromothiophene-2-carboxamido)-N-(5-(3-(dimethylamino) propylcarbamoyl)-1-methyl-1H-pyrrol-3-yl)-1-methyl-1H-pyrrole-2-carboxamide 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 0.18h， 以55%的产率得到4-(2,2'-bithiophene-5-carboxamido)-N-(5-(3-(dimethylamino)propylcarbamoyl)-1-methyl-1H-pyrrol-3-yl)-1-methyl-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Synthesis, anti-mycobacterial activity and DNA sequence-selectivity of a library of biaryl-motifs containing polyamides

  摘要：

  The alarming rise of extensively drug-resistant tuberculosis (XDR-TB) strains, compel the development of new molecules with novel modes of action to control this world health emergency. Distamycin analogues containing N-terminal biaryl-motifs 2(1-5)(1-7) were synthesised using a solution-phase approach and evaluated for their anti-mycobacterial activity and DNA-sequence selectivity. Thiophene dimer motif-containing polyamide 2(2,6) exhibited 10-fold higher inhibitory activity against Mycobacterium tuberculosis compared to distamycin and library member 2(5,7) showed high binding affinity for the 5'-ACATAT-3' sequence. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.001
• 作为产物：
  描述：

  2,2,2-三氯-1-(1-甲基-1H-吡咯-2-基)-乙酮 在 palladium 10% on activated carbon 、 氢气 、 硝酸 、 乙酸酐 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， -40.0~20.0 ℃ 、275.8 kPa 条件下， 反应 19.0h， 生成 4-(5-bromothiophene-2-carboxamido)-N-(5-(3-(dimethylamino) propylcarbamoyl)-1-methyl-1H-pyrrol-3-yl)-1-methyl-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Synthesis, anti-mycobacterial activity and DNA sequence-selectivity of a library of biaryl-motifs containing polyamides

  摘要：

  The alarming rise of extensively drug-resistant tuberculosis (XDR-TB) strains, compel the development of new molecules with novel modes of action to control this world health emergency. Distamycin analogues containing N-terminal biaryl-motifs 2(1-5)(1-7) were synthesised using a solution-phase approach and evaluated for their anti-mycobacterial activity and DNA-sequence selectivity. Thiophene dimer motif-containing polyamide 2(2,6) exhibited 10-fold higher inhibitory activity against Mycobacterium tuberculosis compared to distamycin and library member 2(5,7) showed high binding affinity for the 5'-ACATAT-3' sequence. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.001