(2,5-Dioxopyrrolidin-1-yl) 1-methyl-4-[[1-methyl-4-[(1-methylpyrrole-2-carbonyl)amino]pyrrole-2-carbonyl]amino]pyrrole-2-carboxylate | 295805-56-0

• 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: (2,5-Dioxopyrrolidin-1-yl) 1-methyl-4-[[1-methyl-4-[(1-methylpyrrole-2-carbonyl)amino]pyrrole-2-carbonyl]amino]pyrrole-2-carboxylate
• CAS: 295805-56-0
• 化学式: C₂₂H₂₂N₆O₆
• 分子量: 466.453
• InChiKey: MXYZFODCDLCVBQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  137
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2,5-Dioxopyrrolidin-1-yl) 1-methyl-4-[[1-methyl-4-[(1-methylpyrrole-2-carbonyl)amino]pyrrole-2-carbonyl]amino]pyrrole-2-carboxylate 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 1.33h， 生成 N-[5-[2-[(2-bromoacetyl)amino]ethylcarbamoyl]-1-methylpyrrol-3-yl]-1-methyl-4-[(1-methylpyrrole-2-carbonyl)amino]pyrrole-2-carboxamide
  参考文献：
  名称：

  Novel distamycin analogues: facile synthesis of cholesterol conjugates of distamycin-like oligopeptides

  摘要：

  A facile route towards the synthesis of the first examples of cholesterol-conjugated distamycin analogues is described. These compounds retain their strong binding capacity to double-stranded (ds)-DNA. Aqueous suspensions of these analogues exhibited closed, vesicle-like structures under transmission electron microscope. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)00489-0
• 作为产物：
  描述：

  1-甲基吡咯-2-羰酰氯 在 sodium hydroxide 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (2,5-Dioxopyrrolidin-1-yl) 1-methyl-4-[[1-methyl-4-[(1-methylpyrrole-2-carbonyl)amino]pyrrole-2-carbonyl]amino]pyrrole-2-carboxylate
  参考文献：
  名称：

  Distamycin Analogues without Leading Amide at Their N-Termini − Comparative Binding Properties to AT- and GC-Rich DNA Sequences

  摘要：

  DOI：

  10.1002/1099-0690(200211)2002:21<3604::aid-ejoc3604>3.0.co;2-x

文献信息

• Novel Oligopyrrole Carboxamide based Nickel(II) and Palladium(II) Salens, Their Targeting of Human G-Quadruplex DNA, and Selective Cancer Cell Toxicity
  作者：Asfa Ali、Mohini Kamra、Soma Roy、K. Muniyappa、Santanu Bhattacharya

  DOI：10.1002/asia.201600655

  日期：2016.9.20

  DNA targeting by various metal complexes is a key strategy toward the restriction of cancer cell proliferation. Toward this end, we designed and synthesized novel salen‐based NiII and PdII metal complexes with positively charged flanking side chains comprising N‐methylpyrrole carboxamides of varying lengths. The compounds showed high specificity toward G‐quadruplex DNA over duplex DNA. Sufficient inhibition

  各种金属配合物靶向DNA是限制癌细胞增殖的关键策略。为此，我们设计并合成了基于新型塞伦的Ni II和Pd II金属配合物，该配合物具有带正电荷的侧翼侧链，其中N-长度不同的甲基吡咯羧酰胺。该化合物对G-四链体DNA的特异性高于双链体DNA。观察到对端粒酶活性的充分抑制，这可以通过长期细胞生存力和端粒酶抑制试验中癌细胞增殖的显着限制来确定。这些化合物在凋亡途径后表现出选择性的癌细胞死亡。结合模式的分析表明，Salen部分在G-tetrads上部分堆叠，并且寡聚吡咯侧链羧酰胺侧链单元与凹槽相关。四键结合的金属salen核与凹槽定向的柔性寡吡咯部分的缀合导致人类G-四链体DNA结构的高选择性和稳定性。
• Specific stabilization of promoter G-Quadruplex DNA by 2,6-disubstituted amidoanthracene-9,10-dione based dimeric distamycin analogues and their selective cancer cell cytotoxicity
  作者：Soma Roy、Asfa Ali、Mohini Kamra、Kalappa Muniyappa、Santanu Bhattacharya

  DOI：10.1016/j.ejmech.2020.112202

  日期：2020.6

  potency of the compounds to stabilize the G4 DNA has been shown from the thermal denaturation experiments. The compound interacts with c-MYC G-quadruplex DNA through stacking mode as obtained from ethidium bromide displacement assay, cyclic voltammetric titration, and docking experiments. Molecular modeling studies suggested that the stacking of the anthraquinone moiety over the G-tetrad of the G4 structures

  我们已经设计并合成了含有蒽醌的化合物，这些化合物具有不同长度的寡吡咯侧链。这些化合物稳定了在c-MYC癌基因的启动子区域中形成的G-四链体DNA，选择性地超过了双链体DNA。使用紫外可见光谱滴定，荧光测量和圆二色性（CD）光谱滴定记录这些观察结果。从热变性实验已经显示出化合物稳定G4 DNA的效力。该化合物通过堆叠模式与c-MYC G-四链体DNA相互作用，该堆叠模式是从溴化乙锭置换试验，循环伏安滴定和对接实验中获得的。分子模型研究表明，蒽醌部分在G4结构的G-四联体上的堆积负责这种四链体二级结构的稳定性。此外，在上述化合物存在下，聚合酶终止试验也支持稳定的G4结构的形成。根据基于MTT的细胞生存力测定法确定的化合物，在体外条件下，该化合物对正常细胞（NIH3T3和HDFa）具有选择性的癌细胞（HeLa和HEK293T）细胞毒性。从膜联蛋白V-FITC和PI双重染色测定法中发现，凋亡是癌细胞细胞毒性的机制途径，其通过AO
• Facile synthesis of oligopeptide distamycin analogs devoid of hydrogen bond donors or acceptors at the N-terminus: sequence-specific duplex DNA binding as a function of peptide chain length
  作者：Santanu Bhattacharya、Mini Thomas

  DOI：10.1016/s0040-4039(00)00802-9

  日期：2000.7

  The first examples of distamycin analogs, which lack hydrogen bond interactor groups at the N-terminus, have been synthesized. The bispyrrole peptide did not exhibit any detectable binding with double-stranded (ds) DNA. However, all other homologues did bind to ds-DNA strongly, with the binding affinities increasing as a function of the number of repeating pyrrole carboxamide units, implying that a hydrogen bond donor or acceptor atom per se at the N-terminus is not essential for their DNA binding. Studies with poly d(GC) showed that the N-terminal formamide is not a prerequisite for GC binding, contrary to earlier postulations. (C) 2000 Elsevier Science Ltd. All rights reserved.