N-[5-({[5-({[3-amino-3-(N-methylcarbamoyl)ethyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide | 863319-29-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[5-({[5-({[3-amino-3-(N-methylcarbamoyl)ethyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide
• 英文别名: N-[5-({[5-({[2-(methylcarbamoyl)ethyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide
• CAS: 863319-29-3
• 化学式: C₂₃H₂₈N₈O₅
• 分子量: 496.526
• InChiKey: ZOSHTSXHQNLFSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.64
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  160.29
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-[5-({[5-({[3-amino-3-(N-methylcarbamoyl)ethyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 4-amino-N-[5-({[5-({[2-(N-methylcarbamoyl)ethyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-1-methyl-1H-pyrrole-2-carboxamide hydrochloride
  参考文献：
  名称：

  Design, Synthesis and Growth Inhibition Activity of Bis-Epoxyethyl Derivatives of Stallimycin Modified on the Amidino Moiety

  摘要：

  Derivatives 3-6 of stallimycin (distamycin A) rnodified a t the C-terminal amidine moiety and tethered to a bis-epoxyethyl moiety (as DNA alkylating unit) at the N-terminal position have been prepared and tested for in vitro cytotoxic activity against two different leukemik cell lines, K562 and L1210. None of the compounds without epoxide was active. A comparison of the biological activity related to the diepoxy compounds 3-6 with different non-basic amidine modified moieties, showed low activity for the carbamoyl and N-methyl carbamoyl derivatives (compounds 5 and 6, respectively), moderate activity for the amidoxime analogue 4, good activity for the cyanamidine derivative 3.

  DOI：

  10.1007/s00044-004-0034-6
• 作为产物：
  描述：

  4-(4-(4-formamido-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylic acid 、 3-氨基-N-甲基丙酰胺盐酸盐 在 N,N-二异丙基乙胺 、 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 18.17h， 以74%的产率得到N-[5-({[5-({[3-amino-3-(N-methylcarbamoyl)ethyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Structural and Conformational Requisites in DNA Quadruplex Groove Binding: Another Piece to the Puzzle

  摘要：

  The study of DNA G-quadruplex stabilizers has enjoyed a great momentum in the late years due to their application as anticancer agents. The recognition of the grooves of these structural motifs is expected to result in a higher degree of selectivity over other DNA structures. Therefore, to achieve an enhanced knowledge on the structural and conformational requisites for quadruplex groove recognition, distamycin A, the only compound for which a pure groove binding has been proven, has been chemically modified. Surprisingly, structural and thermodynamic studies revealed that the absence of Coulombic interactions results in an unprecedented binding position in which both the groove and the 3' end of the DNA are occupied. This further contribution adds another piece to the so far elusive puzzle of the recognition between ligands and DNA quadruplexes and will serve as a platform for a rational design of new groove binders.

  DOI：

  10.1021/ja1003872