4-(乙酰基氨基)-1-甲基-1H-咪唑-2-羧酸 | 225667-16-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-(乙酰基氨基)-1-甲基-1H-咪唑-2-羧酸
• 英文名称: 4-Acetylamino-1-methyl-1H-imidazole-2-carboxylic acid
• 英文别名: 1H-Imidazole-2-carboxylicacid, 4-(acetylamino)-1-methyl-；4-acetamido-1-methylimidazole-2-carboxylic acid
• CAS: 225667-16-3
• 化学式: C₇H₉N₃O₃
• mdl: MFCD18808540
• 分子量: 183.167
• InChiKey: ZUODGWGABLNXMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(乙酰基氨基)-1-甲基-1H-咪唑-2-羧酸 在 sodium hydroxide 、 水 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 为溶剂， 生成 4-[(4-Acetylamino-1-methyl-1H-imidazole-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Sequence-Specific DNA Alkylation by Hybrid Molecules between Segment A of Duocarmycin A and Pyrrole/Imidazole Diamide

  摘要：

  In the absence of distamycin A (Dist), hybrids 1 (X=N, CH) selectively alkylate the 3' end of adenine in AT-rich DNA sequences. However, these hybrids can form a heterodimer with Dist to alkylate G residues of predetermined DNA sequences efficiently and with high selectivity.

  DOI：

  10.1002/(sici)1521-3773(19990301)38:5<650::aid-anie650>3.0.co;2-o
• 作为产物：
  描述：

  4-氨基-N-甲基咪唑-2-羧酸乙酯盐酸盐 在 吡啶 、 sodium hydroxide 、 水 、 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 生成 4-(乙酰基氨基)-1-甲基-1H-咪唑-2-羧酸
  参考文献：
  名称：

  Sequence-Specific DNA Alkylation by Hybrid Molecules between Segment A of Duocarmycin A and Pyrrole/Imidazole Diamide

  摘要：

  In the absence of distamycin A (Dist), hybrids 1 (X=N, CH) selectively alkylate the 3' end of adenine in AT-rich DNA sequences. However, these hybrids can form a heterodimer with Dist to alkylate G residues of predetermined DNA sequences efficiently and with high selectivity.

  DOI：

  10.1002/(sici)1521-3773(19990301)38:5<650::aid-anie650>3.0.co;2-o

文献信息

• Rational Design of Sequence-Specific DNA Alkylating Agents Based on Duocarmycin A and Pyrrole−Imidazole Hairpin Polyamides
  作者：Zhi-Fu Tao、Tsuyoshi Fujiwara、Isao Saito、Hiroshi Sugiyama

  DOI：10.1021/ja983398w

  日期：1999.6.1

  Synthesis of novel conjugates between segment A of Duocarmycin A (Du) and N-methylimidazole (Im)−N-methylpyrrole (Py) hairpin polyamides and their DNA alkylation are described. The conjugates PyPyPyγImPyPyDu (8a) and ImPyPyγImPyPyDu (8b) were designed to alkylate the target sequences (A/T)G(A/T)2N(A/G) and (A/T)G(A/T)CN(A/G), respectively, according to Dervan's ring-pairing rule. High-resolution denaturing

  描述了 Duocarmycin A (Du) 的 A 段与 N-甲基咪唑 (Im)-N-甲基吡咯 (Py) 发夹聚酰胺之间的新型偶联物的合成及其 DNA 烷基化。共轭物 PyPyPyγImPyPyDu (8a) 和 ImPyPyγImPyPyDu (8b) 设计用于将目标序列 (A/T)G(A/T)2N(A/G) 和 (A/T)G(A/T)CN(A) 烷基化/G)，分别根据 Dervan 的环配对规则。高分辨率变性凝胶电泳表明，8a 仅将 5'-TGTAAAA-3' 的 A 烷基化了约 400 bp DNA 片段。类似地，8b 的烷基化仅发生在 5'-AGTCAGA-3' 序列的 G 处，在纳摩尔浓度下有效。为了更好地了解这些偶联物烷基化 DNA 的结构，研究了非自我互补双链体十核苷酸 ODN1 和 ODN2 的烷基化。
• Recognition of 5‘-(A,T)GG(A,T)₂-3‘ Sequences in the Minor Groove of DNA by Hairpin Polyamides
  作者：Michelle E. Parks、Eldon E. Baird、Peter B. Dervan

  DOI：10.1021/ja9607289

  日期：1996.1.1

  A series of four hairpin pyrrole-imidazole polyamides, ImImPy-gamma-PyPyPy-beta-Dp, PyPyPy-gamma-ImImPy-beta-Dp, AcImImPy-gamma-PyPyPy-beta-Dp, and AcPyPyPy-gamma-ImImPy-beta-Dp (Im = N-methylimidazole-2-carboxamide, Py = N-methylpyrrole-2-carboxamide, Dp = N,N-dimethylaminopropylamide, gamma = gamma-aminobutyric acid, beta = p-alanine, and Ac = acetyl), designed for recognition of 5'-(A,T)GG(A,T)(2)-3' sequences in the minor groove of DNA were synthesized using solid phase methodology and analyzed with respect to DNA binding affinity and sequence specificity. Quantitative DNase I footprint titration experiments reveal that the optimal polyamide ImImPy-gamma-PyPyPy-beta-Dp binds a designated 5'-TGGTT-3' match site with an equilibrium association constant of K-a = 1.0 x 10(8) M(-1) and the single base pair mismatch sites, 5'-TGTTA-3' and 5'-GGGTA-3', with 50-fold and 100-fold-lower affinity, respectively (10 mM Tris HCl, 10 mM KCl, 10 mM MgCl2, and 5 mM CaCl2, pH 7.0 and 22 degrees C). Polyamides of sequence composition AcImImPy-gamma-PyPyPy-beta-Dp and AcPyPyPy-gamma-ImImPy-beta-Dp, which differ only by the position of the gamma-linker, bind with similar affinities and specificities. Recognition of sequences containing contiguous G . C base pairs expands the sequence repertoire available for targeting DNA with pyrrole-imidazole polyamides.
• Sequence-Specific DNA Alkylation by Hybrid Molecules between Segment A of Duocarmycin A and Pyrrole/Imidazole Diamide
  作者：Zhi-Fu Tao、Tsuyoshi Fujiwara、Isao Saito、Hiroshi Sugiyama

  DOI：10.1002/(sici)1521-3773(19990301)38:5<650::aid-anie650>3.0.co;2-o

  日期：1999.3.1

  In the absence of distamycin A (Dist), hybrids 1 (X=N, CH) selectively alkylate the 3' end of adenine in AT-rich DNA sequences. However, these hybrids can form a heterodimer with Dist to alkylate G residues of predetermined DNA sequences efficiently and with high selectivity.