N-(3-[4-methylpiperazin-1-yl]propyl)-4-nitro-(4-(1-methylpyrrole-2-carboxamido)-1-methylpyrrole-2-carboxamide | 299974-85-9

• 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-(3-[4-methylpiperazin-1-yl]propyl)-4-nitro-(4-(1-methylpyrrole-2-carboxamido)-1-methylpyrrole-2-carboxamide
• 英文别名: 1-methyl-4-(3-(1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxamido)propyl)piperazine
• CAS: 299974-85-9
• 化学式: C₂₀H₂₉N₇O₄
• 分子量: 431.495
• InChiKey: MPHPLGLFEFLWIM-UHFFFAOYSA-N

物化性质

• 沸点：
  600.5±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  117.68
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-(3-[4-methylpiperazin-1-yl]propyl)-4-nitro-(4-(1-methylpyrrole-2-carboxamido)-1-methylpyrrole-2-carboxamide 在 palladium on activated charcoal 氢气 作用下， 以 异丙醇 为溶剂， 生成 4-amino-1-methyl-N-(1-methyl-5-((3-(4-methylpiperazin-1-yl)propyl)carbamoyl)-1H-pyrrol-3-yl)-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  一些头对头连接的DNA小沟结合剂的合成

  摘要：

  已经制备了一系列首尾相连的杂环氨基酸二聚体，用于研究与DNA小沟结合的亲和力和选择性。合成目标的选择由基于计算机的设计主导。已经包括几种新颖的二羧酸连接基，包括吲哚，菲，芴酮和双苯并噻吩。通过印迹分析与DNA的结合表明对衍生自2,7-二氢菲二羧酸的化合物具有很高的亲和力，并且对包含至少4个AT对的AT富集区域具有主要选择性，但具有跨越两个CG碱基对的能力。

  DOI：

  10.1016/s0040-4020(00)00432-4
• 作为产物：
  描述：

  1-甲基-4-硝基吡咯-2-羧酸 在 palladium on activated charcoal 盐酸 、 氯化亚砜 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 生成 N-(3-[4-methylpiperazin-1-yl]propyl)-4-nitro-(4-(1-methylpyrrole-2-carboxamido)-1-methylpyrrole-2-carboxamide
  参考文献：
  名称：

  一些头对头连接的DNA小沟结合剂的合成

  摘要：

  已经制备了一系列首尾相连的杂环氨基酸二聚体，用于研究与DNA小沟结合的亲和力和选择性。合成目标的选择由基于计算机的设计主导。已经包括几种新颖的二羧酸连接基，包括吲哚，菲，芴酮和双苯并噻吩。通过印迹分析与DNA的结合表明对衍生自2,7-二氢菲二羧酸的化合物具有很高的亲和力，并且对包含至少4个AT对的AT富集区域具有主要选择性，但具有跨越两个CG碱基对的能力。

  DOI：

  10.1016/s0040-4020(00)00432-4

文献信息

• Synthesis and biophysical evaluation of minor-groove binding C-terminus modified pyrrole and imidazole triamide analogs of distamycin
  作者：Toni Brown、Zarmeen Taherbhai、Jim Sexton、Arden Sutterfield、Mark Turlington、Justin Jones、Lindsay Stallings、Michelle Stewart、Karen Buchmueller、Hilary Mackay

  DOI：10.1016/j.bmc.2006.09.037

  日期：2007.1.1

  Five polyamide derivatives with rationally modified C-terminus moieties were synthesized and their DNA binding specificity and affinity determined. A convergent approach was employed to synthesize polyamides containing an alkylaminopiperazine (4 and 5), a truncated piperazine (6), or an alkyldiamino-C-terminus moiety (7 and 8) with two specific objectives: to investigate the effects of number of potential cationic centers and steric bulk at the C-terminus. CD studies confirmed that compounds 4, 5, 7, and 8 bind in the minor groove of DNA. The alkylpiperazine containing compounds (4 and 5) showed only moderate binding to DNA with AT values of 2.8 and 8.3 degrees C with their cognate sequence, respectively. The alkyldiamino compounds (7 and 8) were more impressive producing a Delta T-m of > 17 and > 22 degrees C, respectively. Compound 6 (truncated piperazine) did not stabilize its cognate DNA sequence. Footprints were observed for all compounds (except compound 6) with their cognate DNA sequence using DNase I footprinting, with compound 7 producing a footprint of 0.1 mu M at the expected 5'-ACGCGT-3' site. SPR analysis of compound 7 bindiy to 5'-ACGCGT-3', 5'-ACCGGT-3', and 5'-AAATTT-3' produced binding affinities of 2.2 x 10(6), 3.3 x 10(5), and 1 x 10(5) M-1, respectively, indicating a preference for its cognate sequence of 5'-ACGCGT-3'. These results are in good agreement with the footprinting data. The results indicate that steric crowding at the C-terminus is important with respect to binding. However, the number of cationic centers within the molecule may also play a role. The alkyldiamino-containing compounds (7 and 8) warrant further investigation in the field of polyamide research. (c) 2006 Elsevier Ltd. All rights reserved.