N-[4-[[hydroxy-[(2-methylpropan-2-yl)oxy]methylidene]azaniumylmethyl]phenyl]-1-methyl-4-nitropyrrole-2-carboximidate | 265664-81-1

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: N-[4-[[hydroxy-[(2-methylpropan-2-yl)oxy]methylidene]azaniumylmethyl]phenyl]-1-methyl-4-nitropyrrole-2-carboximidate
• CAS: 265664-81-1
• 化学式: C₁₈H₂₂N₄O₅
• 分子量: 374.396
• InChiKey: CDCFGTWNHXEPMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[4-[[hydroxy-[(2-methylpropan-2-yl)oxy]methylidene]azaniumylmethyl]phenyl]-1-methyl-4-nitropyrrole-2-carboximidate 在 镍 N-甲基吡咯烷酮 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 60.0 ℃ 、3.0 MPa 条件下， 生成 [4-({4-[4-(tert-Butoxycarbonylamino-methyl)-benzoylamino]-1-methyl-1H-pyrrole-2-carbonyl}-amino)-benzyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis, DNA binding, topoisomerases inhibition and cytotoxic properties of 4-arylcarboxamidopyrrolo-2-carboxyanilides

  摘要：

  Three 4-arylcarboxamidopyrrolo-2-carboxyanilides bearing different substituents on the pyrrole nitrogen were synthesized and evaluated for their capacities to bind to specific sequences within the minor groove of DNA and to inhibit human topoisomerases I and II in vitro. The cytotoxicity of the drugs correlates with their DNA binding affinities. The two drugs bearing a N-methyl or N-benzyl pyrrole stabilize topoisomerase I-DNA complexes. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00028-7
• 作为产物：
  描述：

  对硝基苯甲腈 在 palladium on activated charcoal sodium hydroxide 、 二甲基硫 、 硼烷 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[4-[[hydroxy-[(2-methylpropan-2-yl)oxy]methylidene]azaniumylmethyl]phenyl]-1-methyl-4-nitropyrrole-2-carboximidate
  参考文献：
  名称：

  Synthesis, DNA binding, topoisomerases inhibition and cytotoxic properties of 4-arylcarboxamidopyrrolo-2-carboxyanilides

  摘要：

  Three 4-arylcarboxamidopyrrolo-2-carboxyanilides bearing different substituents on the pyrrole nitrogen were synthesized and evaluated for their capacities to bind to specific sequences within the minor groove of DNA and to inhibit human topoisomerases I and II in vitro. The cytotoxicity of the drugs correlates with their DNA binding affinities. The two drugs bearing a N-methyl or N-benzyl pyrrole stabilize topoisomerase I-DNA complexes. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00028-7

文献信息

• Synthesis, DNA binding, topoisomerases inhibition and cytotoxic properties of 4-arylcarboxamidopyrrolo-2-carboxyanilides
  作者：Fabienne Dudouit、Jean-François Goossens、Raymond Houssin、Jean-Pierre Hénichart、Pierre Colson、Claude Houssier、Nathalie Gelus、Christian Bailly

  DOI：10.1016/s0960-894x(00)00028-7

  日期：2000.3

  Three 4-arylcarboxamidopyrrolo-2-carboxyanilides bearing different substituents on the pyrrole nitrogen were synthesized and evaluated for their capacities to bind to specific sequences within the minor groove of DNA and to inhibit human topoisomerases I and II in vitro. The cytotoxicity of the drugs correlates with their DNA binding affinities. The two drugs bearing a N-methyl or N-benzyl pyrrole stabilize topoisomerase I-DNA complexes. (C) 2000 Elsevier Science Ltd. All rights reserved.