Methyl 4-[[4-(4-carbazol-9-ylbutanoylamino)-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Methyl 4-[[4-(4-carbazol-9-ylbutanoylamino)-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carboxylate
• 化学式: C₂₉H₂₉N₅O₄
• 分子量: 511.58
• InChiKey: NYBIAEWYLKPJOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  99.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-甲基-4-硝基吡咯-2-羧酸 在 palladium on activated charcoal 4-二甲氨基吡啶 、 硫酸 、 氢气 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 39.5h， 生成 Methyl 4-[[4-(4-carbazol-9-ylbutanoylamino)-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carboxylate
  参考文献：
  名称：

  Design, synthesis, DNA-binding and cytotoxicity evaluation of new potential combilexines

  摘要：

  Combilexines, compounds in which a DNA intercalator is linked to a minor groove binding component, interact with the DNA in a sequence specific manner to yield in most cases compounds with anticancer activity. A series of new compounds closely related to netropsin in which the two components were linked by an amide group was synthesised as potential combilexines. As some of these compounds showed cytotoxic activity in vitro, an attempt was made to rationalise their mechanism of action. The DNA binding characteristics of the carboxamides were evaluated by thermal denaturation experiments and by ethidium bromide displacement assay. Their ability to inhibit the topoisomerase I was also determined. It was concluded that the new compounds were only weak DNA ligands although able in some cases to inhibit topoisomerase I. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01349-1

文献信息

• Design, synthesis, DNA-binding and cytotoxicity evaluation of new potential combilexines
  作者：Christian Hotzel、Annalisa Marotto、Ulf Pindur

  DOI：10.1016/s0223-5234(02)01349-1

  日期：2002.5

  Combilexines, compounds in which a DNA intercalator is linked to a minor groove binding component, interact with the DNA in a sequence specific manner to yield in most cases compounds with anticancer activity. A series of new compounds closely related to netropsin in which the two components were linked by an amide group was synthesised as potential combilexines. As some of these compounds showed cytotoxic activity in vitro, an attempt was made to rationalise their mechanism of action. The DNA binding characteristics of the carboxamides were evaluated by thermal denaturation experiments and by ethidium bromide displacement assay. Their ability to inhibit the topoisomerase I was also determined. It was concluded that the new compounds were only weak DNA ligands although able in some cases to inhibit topoisomerase I. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.