benzyl 3-<4-(4-formamido-1-methylpyrrole-2-carbamido)-1-methylpyrrole-2-carbamido>-1-methylpyrazole-5-carboxylate | 158811-80-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 3-<4-(4-formamido-1-methylpyrrole-2-carbamido)-1-methylpyrrole-2-carbamido>-1-methylpyrazole-5-carboxylate
• CAS: 158811-80-4
• 化学式: C₂₅H₂₅N₇O₅
• 分子量: 503.517
• InChiKey: QPAWUTRFIQLGGW-UHFFFAOYSA-N

物化性质

• 沸点：
  669.8±55.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  141.28
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  benzyl 3-<4-(4-formamido-1-methylpyrrole-2-carbamido)-1-methylpyrrole-2-carbamido>-1-methylpyrazole-5-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到3-<4-(4-formamido-1-methylpyrrole-2-carbamido)-1-methylpyrrole-2-carbamido>-1-methylpyrazole-5-carboxylic acid
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Three Pyrazole Analogues of Distamycin A.

  摘要：

  The synthesis of three new monopyrazole analogues of the antiviral compound distamycin A is reported. Suitably protected 4-amino-1-methylpyrrole-2-carboxylic acid and 3-amino-1-methylpyrazole-5-carboxylic acid derivatives were chosen as starting materials. The construction of the trimeric polyamide framework was accomplished by assembly of the monomeric precursors under condensing conditions by analogy with our previous methodology, although with significant improvements in some pivotal steps. After chromatographic purification and spectroscopic characterisation, the analogues were assayed for antiviral activity. Compounds 7a-c inhibited vaccinia virus at a concentration similar to or lower than distamycin A and the related antibiotic netropsin. Analogues 7b and 7c exhibited an antiviral effect comparable to those of distamycin A and netropsin against HSV-1 and HSV-2, whereas their antiviral activity against several other viruses including HIV-1 and HIV-2 was somewhat lower. The cellular toxicity of 7a-c toward different host cell types proved to be of similar magnitude or lower than those of distamycin A and netropsin.

  DOI：

  10.3891/acta.chem.scand.48-0498
• 作为产物：
  描述：

  benzyl 4-(3-tert-butoxycarbonylamino-1-methylpyrrole-2-carbamide)-1-methylpyrazole-5-carboxylate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 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 48.0h， 生成 benzyl 3-<4-(4-formamido-1-methylpyrrole-2-carbamido)-1-methylpyrrole-2-carbamido>-1-methylpyrazole-5-carboxylate
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Three Pyrazole Analogues of Distamycin A.

  摘要：

  The synthesis of three new monopyrazole analogues of the antiviral compound distamycin A is reported. Suitably protected 4-amino-1-methylpyrrole-2-carboxylic acid and 3-amino-1-methylpyrazole-5-carboxylic acid derivatives were chosen as starting materials. The construction of the trimeric polyamide framework was accomplished by assembly of the monomeric precursors under condensing conditions by analogy with our previous methodology, although with significant improvements in some pivotal steps. After chromatographic purification and spectroscopic characterisation, the analogues were assayed for antiviral activity. Compounds 7a-c inhibited vaccinia virus at a concentration similar to or lower than distamycin A and the related antibiotic netropsin. Analogues 7b and 7c exhibited an antiviral effect comparable to those of distamycin A and netropsin against HSV-1 and HSV-2, whereas their antiviral activity against several other viruses including HIV-1 and HIV-2 was somewhat lower. The cellular toxicity of 7a-c toward different host cell types proved to be of similar magnitude or lower than those of distamycin A and netropsin.

  DOI：

  10.3891/acta.chem.scand.48-0498