N-<<1-Methyl-4-<1-methyl-4-(guanidinoacetamido)pyrrole-2-carboxamido>pyrrol-2-yl>carbonyl>-L-alanyl-L-alanyl-L-alanine tert-butyl ester acetate | 119437-09-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-<<1-Methyl-4-<1-methyl-4-(guanidinoacetamido)pyrrole-2-carboxamido>pyrrol-2-yl>carbonyl>-L-alanyl-L-alanyl-L-alanine tert-butyl ester acetate
• 英文别名: N-({1-Methyl-4-[1-methyl-4-(guanidinoacetamido)pyrrole-2-carboxamido]pyrrol-2-yl}carbonyl)-L-alanyl-L-alanyl-L-alanine tert-butyl ester acetate
• CAS: 119437-09-1
• 化学式: C₂H₄O₂*C₂₈H₄₁N₉O₇
• 分子量: 675.742
• InChiKey: AFNMAVURZZLYEG-NLQWVURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.44
• 重原子数：
  48.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  268.83
• 氢给体数：
  8.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-<<1-Methyl-4-<1-methyl-4-(guanidinoacetamido)pyrrole-2-carboxamido>pyrrol-2-yl>carbonyl>-L-alanyl-L-alanyl-L-alanine tert-butyl ester acetate 、 三氟乙酸 以82%的产率得到N-<<1-Methyl-4-<1-methyl-4-(guanidinoacetamido)pyrrole-2-carboxamido>pyrrol-2-yl>carbonyl>-L-alanyl-L-alanyl-L-alanine trifluoroacetate
  参考文献：
  名称：

  Synthesis, DNA binding and biological evaluation of synthetic precursors and novel analogs of netropsin

  摘要：

  A series of oligopeptides have been synthesized that are structurally related to the natural agent netropsin. The binding constants to double-stranded polynucleotides as well as the cytostatic activity against both murine human tumor cell lines and the in vitro activity against a range of DNA and RNA viruses have been determined for these novel compounds and some of their synthetic precursors. 1-Methyl-5-nitropyrrole-2-carboxylic acid methyl ester (4), N-[[1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrol-2- yl]carbonyl]-L-alanine tert-butyl ester (28), and N-[[1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrol-2- yl]carbonyl]-L-alanyl-L-alanine tert-butyl ester (29) showed modest inhibitory effect on tumor cell proliferation (CD50 = 26-85 micrograms/mL). Of all the compounds that were evaluated, 28 proved the most potent antiviral agent. It was inhibitory to parainfluenza-3 virus and Coxsackie virus B4 in Vero cells at a concentration of 20 micrograms/mL.

  DOI：

  10.1021/jm00125a024
• 作为产物：
  描述：

  1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxylic acid 在 1,8-双二甲氨基萘 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-<<1-Methyl-4-<1-methyl-4-(guanidinoacetamido)pyrrole-2-carboxamido>pyrrol-2-yl>carbonyl>-L-alanyl-L-alanyl-L-alanine tert-butyl ester acetate
  参考文献：
  名称：

  Synthesis, DNA binding and biological evaluation of synthetic precursors and novel analogs of netropsin

  摘要：

  A series of oligopeptides have been synthesized that are structurally related to the natural agent netropsin. The binding constants to double-stranded polynucleotides as well as the cytostatic activity against both murine human tumor cell lines and the in vitro activity against a range of DNA and RNA viruses have been determined for these novel compounds and some of their synthetic precursors. 1-Methyl-5-nitropyrrole-2-carboxylic acid methyl ester (4), N-[[1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrol-2- yl]carbonyl]-L-alanine tert-butyl ester (28), and N-[[1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrol-2- yl]carbonyl]-L-alanyl-L-alanine tert-butyl ester (29) showed modest inhibitory effect on tumor cell proliferation (CD50 = 26-85 micrograms/mL). Of all the compounds that were evaluated, 28 proved the most potent antiviral agent. It was inhibitory to parainfluenza-3 virus and Coxsackie virus B4 in Vero cells at a concentration of 20 micrograms/mL.

  DOI：

  10.1021/jm00125a024