methyl 1-methyl-4-<1-methyl-4-<2'-<2-(N-tert-butoxycarbonyl)aminoethyl>-2,4'-bithiazole-4-carboxamido>pyrrole-2-carboxamido>pyrrole-2-carboxylate | 133765-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 1-methyl-4-<1-methyl-4-<2'-<2-(N-tert-butoxycarbonyl)aminoethyl>-2,4'-bithiazole-4-carboxamido>pyrrole-2-carboxamido>pyrrole-2-carboxylate
• 英文别名: Methyl 1-methyl-4-[[1-methyl-4-[[2-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-thiazol-4-yl]-1,3-thiazole-4-carbonyl]amino]pyrrole-2-carbonyl]amino]pyrrole-2-carboxylate
• CAS: 133765-86-3
• 化学式: C₂₇H₃₁N₇O₆S₂
• 分子量: 613.718
• InChiKey: AVLNIMLEJJVAAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  215
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 1-methyl-4-<1-methyl-4-<2'-<2-(N-tert-butoxycarbonyl)aminoethyl>-2,4'-bithiazole-4-carboxamido>pyrrole-2-carboxamido>pyrrole-2-carboxylate 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 0.17h， 以71%的产率得到methyl 1-methyl-4-<1-methyl-4-<2'-(2-aminoethyl)-2,4'-bithiazole-4-carboxamido>pyrrole-2-carboxamido>pyrrole-2-carboxylate trifluoroacetate
  参考文献：
  名称：

  Synthesis, determination of sequence selective DNA minor groove binding and biological evaluation of hybrid bithiazole-linked netropsin derivatives

  摘要：

  A series of hybrid molecules have been synthesized which result from the combination of a DNA sequence-specific ligand (netropsin) coupled to a DNA-interactive structural component of bleomycins (bithiazole). The DNA binding affinities as well as the cytostatic activity and their in vitro activity against a wide variety of viruses have been determined. Most of the new agents retain the DNA binding capacity of netropsin and distamycin, and force field and Pi calculations reveal the important role of the arc of curvature of these compounds in their binding to DNA. Like netropsin, the evaluated molecules did not show significant antiviral activity, but one of them demonstrated enhanced cytostatic activity against both human and murine tumor cell lines.

  DOI：

  10.1016/0223-5234(92)90146-r
• 作为产物：
  描述：

  2-(叔丁氧羰基氧亚氨基)-2-苯乙腈 在 sodium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 methyl 1-methyl-4-<1-methyl-4-<2'-<2-(N-tert-butoxycarbonyl)aminoethyl>-2,4'-bithiazole-4-carboxamido>pyrrole-2-carboxamido>pyrrole-2-carboxylate
  参考文献：
  名称：

  Synthesis, determination of sequence selective DNA minor groove binding and biological evaluation of hybrid bithiazole-linked netropsin derivatives

  摘要：

  A series of hybrid molecules have been synthesized which result from the combination of a DNA sequence-specific ligand (netropsin) coupled to a DNA-interactive structural component of bleomycins (bithiazole). The DNA binding affinities as well as the cytostatic activity and their in vitro activity against a wide variety of viruses have been determined. Most of the new agents retain the DNA binding capacity of netropsin and distamycin, and force field and Pi calculations reveal the important role of the arc of curvature of these compounds in their binding to DNA. Like netropsin, the evaluated molecules did not show significant antiviral activity, but one of them demonstrated enhanced cytostatic activity against both human and murine tumor cell lines.

  DOI：

  10.1016/0223-5234(92)90146-r