4-oxobenzo[d][1,2,3]triazin-3(4H)-yl 4-formamido-1-methyl-1H-pyrrole-2-carboxylate | 158628-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并-1,2,3-三嗪类化合物
• 英文名称: 4-oxobenzo[d][1,2,3]triazin-3(4H)-yl 4-formamido-1-methyl-1H-pyrrole-2-carboxylate
• CAS: 158628-14-9
• 化学式: C₁₄H₁₁N₅O₄
• 分子量: 313.272
• InChiKey: NILVOFLOXSYNJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.03
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  108.11
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-{[(4-amino-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-N-[3-(dimethylamino)propyl]-1-methyl-1H-pyrrole-2-carboxamide 、 4-oxobenzo[d][1,2,3]triazin-3(4H)-yl 4-formamido-1-methyl-1H-pyrrole-2-carboxylate 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 Distamin
  参考文献：
  名称：

  A New DNA Minor Groove Binding Motif: Cross-Linked Lexitropsins

  摘要：

  The nitrogen atoms of central pyrrole rings on two separate tripyrrolecarboxamide strands were covalently linked through poly(methylene) chains to provide a novel class of lexitropsins potentially capable of B-DNA double-strand reading via the minor groove, CD titration experiments revealed increasingly enhanced binding of 1:1 stoichiometry to the poly(dA-dT)-poly(dA-dT) DNA from the tetrakis(methylene) linkage to the heptakis(methylene) linkage, suggesting gradually growing importance of the bidentate antiparallel side by side binding. Ethidium bromide fluorescence displacement experiments on both poly(dA-dT)-poly(dA-dT) and poly(dA)-poly(dT) DNA's supported this analysis by providing quantitative measurement of intrinsic binding constants. The heptakis(methylene) linkage offered a binding enhancement of approximately 1000 times compared with that of the monomer.

  DOI：

  10.1021/ja00095a001
• 作为产物：
  描述：

  4-氨基-1-甲基-1H-吡咯-2-羧酸甲酯 在 sodium hydroxide 、 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， 反应 7.5h， 生成 4-oxobenzo[d][1,2,3]triazin-3(4H)-yl 4-formamido-1-methyl-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  A New DNA Minor Groove Binding Motif: Cross-Linked Lexitropsins

  摘要：

  The nitrogen atoms of central pyrrole rings on two separate tripyrrolecarboxamide strands were covalently linked through poly(methylene) chains to provide a novel class of lexitropsins potentially capable of B-DNA double-strand reading via the minor groove, CD titration experiments revealed increasingly enhanced binding of 1:1 stoichiometry to the poly(dA-dT)-poly(dA-dT) DNA from the tetrakis(methylene) linkage to the heptakis(methylene) linkage, suggesting gradually growing importance of the bidentate antiparallel side by side binding. Ethidium bromide fluorescence displacement experiments on both poly(dA-dT)-poly(dA-dT) and poly(dA)-poly(dT) DNA's supported this analysis by providing quantitative measurement of intrinsic binding constants. The heptakis(methylene) linkage offered a binding enhancement of approximately 1000 times compared with that of the monomer.

  DOI：

  10.1021/ja00095a001

文献信息

• Chen, Yong-Huang; Lown, J. William, Heterocycles, 1995, vol. 41, # 8, p. 1691 - 1708
  作者：Chen, Yong-Huang、Lown, J. William

  DOI：——

  日期：——
• A New DNA Minor Groove Binding Motif: Cross-Linked Lexitropsins
  作者：Yong-Huang Chen、J. William Lown

  DOI：10.1021/ja00095a001

  日期：1994.8

  The nitrogen atoms of central pyrrole rings on two separate tripyrrolecarboxamide strands were covalently linked through poly(methylene) chains to provide a novel class of lexitropsins potentially capable of B-DNA double-strand reading via the minor groove, CD titration experiments revealed increasingly enhanced binding of 1:1 stoichiometry to the poly(dA-dT)-poly(dA-dT) DNA from the tetrakis(methylene) linkage to the heptakis(methylene) linkage, suggesting gradually growing importance of the bidentate antiparallel side by side binding. Ethidium bromide fluorescence displacement experiments on both poly(dA-dT)-poly(dA-dT) and poly(dA)-poly(dT) DNA's supported this analysis by providing quantitative measurement of intrinsic binding constants. The heptakis(methylene) linkage offered a binding enhancement of approximately 1000 times compared with that of the monomer.