4-(4-(4-formamido-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylic acid | 77716-21-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(4-(4-formamido-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylic acid
• 英文别名: 4-[[4-[(4-Formamido-1-methylpyrrole-2-carbonyl)amino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carboxylic acid
• CAS: 77716-21-3
• 化学式: C₁₉H₂₀N₆O₅
• 分子量: 412.405
• InChiKey: OSXLKVXTCGFPEO-UHFFFAOYSA-N

物化性质

• 熔点：
  178-181 °C
• 沸点：
  610.9±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  139
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  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 在 盐酸 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.42h， 生成 偏端霉素A盐酸盐
  参考文献：
  名称：

  Novel efficient total synthesis of antiviral antibiotic distamycin A

  摘要：

  DOI：

  10.1021/jo00330a022
• 作为产物：
  描述：

  Benzyl 4-Amino-1-methylpyrrole-2-carboxylate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 4-(4-(4-formamido-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  设计，合成，DNA结合和一系列DNA小沟结合插层药物的生物活性。

  摘要：

  合成了一组假肽，天然抗肿瘤剂双歧霉素或netropsin与苯胺基r啶发色团（与合成的抗白血病药物氨茶碱有关）的分子组合。确定并讨论了它们的DNA结合特性，并讨论了它们的结构差异以及与观察到的碱基依赖性结合。结合数据与模型一致，在模型中the啶核占据一个插入位点，而netropsin或distamycin残基位于DNA小沟中。报道了针对鼠细胞系的细胞抑制活性和细胞毒性活性，以及​​对DNA合成的抑制作用的显着差异。

  DOI：

  10.1002/jps.2600781106

文献信息

• [EN] DNA BINDING AGENTS WITH A MINOR GROOVE BINDING TAIL<br/>[FR] AGENTS LIANT L'ADN AVEC UNE QUEUE SE LIANT AU SILLON MINEUR
  申请人：UNIV TEXAS

  公开号：WO2017049091A1

  公开（公告）日：2017-03-23

  Provided herein are compounds which intercalate into the DNA of a cell and are capable of crossing the blood brain barrier of a formula provided herein. Pharmaceutical compositions of the compounds and methods of treating cancer, for example brain, lung, or pancreatic cancer, are also provided herein.

  本文提供的是一些能够插入细胞DNA并能够穿过血脑屏障的化合物。此外，本文还提供了这些化合物的药物组合物以及治疗癌症的方法，例如大脑、肺部或胰腺癌。
• DNA binding agents with a minor groove binding tail
  申请人：Board of Regents, The University of Texas System

  公开号：US10358439B2

  公开（公告）日：2019-07-23

  Provided herein are compounds which intercalate into the DNA of a cell and are capable of crossing the blood brain barrier of a formula provided herein. Pharmaceutical compositions of the compounds and methods of treating cancer, for example brain, lung, or pancreatic cancer, are also provided herein.

  本文提供的化合物可插入细胞的 DNA 中，并能通过本文所提供配方的血脑屏障。本文还提供了这些化合物的药物组合物和治疗癌症（例如脑癌、肺癌或胰腺癌）的方法。
• Synthesis and antiviral activity of distamycin A analogs: substitutions on the different pyrrole nitrogens and in the amidine function
  作者：Leif Grehn、Ulf Ragnarsson、Bertil Eriksson、Bo Oeberg

  DOI：10.1021/jm00361a018

  日期：1983.7

  Several new analogues of the antiviral antibiotic distamycin A were synthesized and assayed for their effects on influenza and herpes simplex virus. The new compounds 5b-j (R1-3 = H, CH3, and C2H5, R4,5 = H and CH3) were obtained via stepwise prepared formylated trimeric benzyl 4-aminopyrrole-2-carboxylates 3a-h, which after catalytic hydrogenolysis were coupled as N-succinimidyl esters directly with the proper beta-aminopropionamidine, unsubstituted or substituted with one or two methyl groups in the amidine function. Most of the new analogues did not exhibit significant effects on the viruses studied, but three compounds (5f-h) displayed activity on herpes virus as demonstrated in plaque formation and virus yield assays. Elevated cytotoxicity was simultaneously observed for 5g and 5h. For compound 5f, a partial separation of antiherpes activity and cytotoxicity was accomplished. The differences in antiherpes activity did not correspond to the differences in the inhibition of herpes virus DNA polymerase.
• Synthesis and evaluation of the hybrid molecules possessing DNA-cleaving activity
  作者：Kozo Shishido、Shigenori Haruna、Chisato Yamamura、Hiromi Iitsuka、Hisao Nemoto、Yasuo Shinohara、Masayuki Shibuya

  DOI：10.1016/s0960-894x(97)10030-0

  日期：1997.10

  The design and synthesis of enantiomerically enriched hybrid molecules, la-e and 2a-c, have been accomplished by employing the lipase-mediated asymmetric acetylation of prochiral diol 9 as the key step. Evaluation of their DNA-cleaving activity has revealed the unnatural type of enantiomer 2a-c to be more potent than la-e with natural configuration. (C) 1997 Elsevier Science Ltd.
• Synthesis of Fluoroquinolone-di- and tri-(N-methylpyrrole) Conjugates
  作者：Ichiro Suzuki、Mayuko Takahashi、Kei Takeda

  DOI：10.3987/com-10-12079

  日期：——

  Some FLQs, such as lomefloxacin and fleroxacin, having two fluorine atoms are known to generate an arylcarbene under photoirradiation conditions leading to DNA damage. We synthesized some conjugates between FLQs and di- and tri-(N-methylpyrrole) that are known as a DNA minor groove binder.