4-amino-N-[2-[[2-[2-(dimethylamino)ethylcarbamoyl]-1-methylimidazol-4-yl]carbamoyl]-1-methylimidazol-4-yl]-1-methylimidazole-2-carboxamide | 147056-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-amino-N-[2-[[2-[2-(dimethylamino)ethylcarbamoyl]-1-methylimidazol-4-yl]carbamoyl]-1-methylimidazol-4-yl]-1-methylimidazole-2-carboxamide
• CAS: 147056-65-3
• 化学式: C₁₉H₂₇N₁₁O₃
• 分子量: 457.495
• InChiKey: NWWRIPRRTANKOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.73
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  170.02
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  4-(1-methyl-4-(1-methyl-4-(1-methyl-1H-pyrrole-2-carboxamido)-1H-imidazole-2-carboxamido)-1H-pyrrole-2-carboxamido)butanoic acid 、 4-amino-N-[2-[[2-[2-(dimethylamino)ethylcarbamoyl]-1-methylimidazol-4-yl]carbamoyl]-1-methylimidazol-4-yl]-1-methylimidazole-2-carboxamide 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 192.0h， 生成
  参考文献：
  名称：

  SOLUTION PHASE SYNTHESIS OF IMIDAZOLE- AND PYRROLE-CONTAINING HAIRPIN POLYAMIDES

  摘要：

  DOI：

  10.1515/hc.2007.13.1.17
• 作为产物：
  描述：

  4-amino-N-[2-[2-(dimethylamino)ethylcarbamoyl]-1-methylimidazol-4-yl]-1-methylimidazole-2-carboxamide 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 4-amino-N-[2-[[2-[2-(dimethylamino)ethylcarbamoyl]-1-methylimidazol-4-yl]carbamoyl]-1-methylimidazol-4-yl]-1-methylimidazole-2-carboxamide
  参考文献：
  名称：

  SOLUTION PHASE SYNTHESIS OF IMIDAZOLE- AND PYRROLE-CONTAINING HAIRPIN POLYAMIDES

  摘要：

  DOI：

  10.1515/hc.2007.13.1.17

文献信息

• In vitro cytotoxicity of GC sequence directed alkylating agents related to distamycin
  作者：Moses Lee、Andrea L. Rhodes、Michael D. Wyatt、Maurizio D'Incalci、Stephen Forrow、John A. Hartley

  DOI：10.1021/jm00059a011

  日期：1993.4

  C-terminus contain a dimethylamino moiety have been shown to selectively bind to the minor groove of GC-rich sequences. Accordingly, these agents were employed as vectors for the delivery of a variety of alkylating agents to GC-rich sequences. The alkylating agents are attached to the N-terminus of these vectors thus providing the benzoyl N-mustards (8, 15, and 18 that contain one, two, and three imidazole

  已显示含咪唑类似物7、10和17的他新霉素，其中C端含有二甲基氨基部分，该咪唑选择性结合富GC序列的短沟。因此，这些试剂被用作载体以将多种烷基化试剂递送至富含GC的序列。烷基化剂连接到这些载体的N-末端，从而提供苯甲酰基N-芥末（分别包含1、2和3个咪唑单元的8、15和18）和取代的乙酰胺11-14。乙酰胺7、10和17以及芥子15和18的乙锭置换试验结果表明，这些试剂与小牛胸腺DNA，poly（dA.dT），poly（dG.dC）以及大肠杆菌T4 DNA结合，从而确认它们在小凹槽中的结合。这些化合物与聚（dA）的结合常数降低。dT）虽然仍比二棉霉素与poly（dG.dC）结合得更牢固或更牢固，但为他们接受GC序列提供了证据。CD滴定研究也表明了对富含GC的序列的选择性。将10、15、17和18滴定至poly（dA.dT）会在约330 nm处产生弱的药物诱导CD谱带；然而，这些药物与等摩尔药物浓度下的聚（dG
• Antitumor Imidazotetrazines. 41. Conjugation of the Antitumor Agents Mitozolomide and Temozolomide to Peptides and Lexitropsins Bearing DNA Major and Minor Groove-Binding Structural Motifs
  作者：Jill Arrowsmith、Sharon A. Jennings、Alan S. Clark、Malcolm F. G. Stevens

  DOI：10.1021/jm020936d

  日期：2002.12.1

  Carboxylic acids derived from the amido groups of the antitumor agents mitozolomide and temozolomide have been conjugated to simple amino acids and peptides by carbodiimide coupling. Solid-state peptide synthesis has been applied to link the acids to DNA major groove-binding peptidic motifs known to adopt alpha-helical conformations. Attachment of the acids to pyrrole and imidazole polyamidic lexitropsins gave a series of potential DNA minor groove- binding ligands. In vitro biological evaluation of a limited number of these novel conjugates failed to demonstrate any enhanced growth-inhibitory activity compared to the unconjugated drugs; sites of alkylation at tracts of multiple guanines were also unaffected. Attachment of additional residues at C-8 of the imidazotetrazines did not perturb the chemistry of activation of the bicyclic nucleus, and biological sequelae can be rationalized by invoking the liberation of a common, diffusible, reactive chemical intermediate, the methanediazonium ion.