3-[1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxamido]propionitrile | 3185-94-2

• 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: 3-[1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxamido]propionitrile
• 英文别名: 1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)-pyrrole-2-carboxamido propionitrile；N-[2-(azaniumylidynemethyl)ethyl]-1-methyl-4-[(1-methyl-4-nitropyrrole-2-carbonyl)amino]pyrrole-2-carboximidate
• CAS: 3185-94-2
• 化学式: C₁₅H₁₆N₆O₄
• 分子量: 344.33
• InChiKey: YRBLVMPWBNBXRW-UHFFFAOYSA-N

物化性质

• 熔点：
  254-255 °C
• 沸点：
  569.1±50.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)
• 溶解度：
  溶于乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxamido]propionitrile 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 88.0h， 生成 3-(1-methyl-4-<1-methyl-4-<4-(2-<7,10,12-trimethyl-6H-<1,3>oxazolo<5,4-c>pyrido<3,4-g>carbazole>)butylcarboxamido>pyrrole-2-carboxamido>)propionitrile acetate
  参考文献：
  名称：

  Synthesis, DNA binding and biological activity of oxazolopyridocarbazole-netropsin hybrid molecules

  摘要：

  A series of bifunctional molecules have been synthesized which result from the combination of a DNA sequence-specific ligand (netropsin) coupled to an intercalator moiety (OPC). The binding constants to double-stranded polynucleotides as well as the cytostatic activity against both murine and human tumor cell lines and the in vitro activity against a range of DNA and RNA viruses (including human immunodeficiency virus) have been determined for these novel molecules. All of them retain the DNA binding affinity of netropsin but with a notable decrease of A-T sequence selectivity. They did not show in vitro antiviral activity. On the other hand, these compounds demonstrated enhanced cytostatic activity against both human and murine tumor cell lines.

  DOI：

  10.1016/0223-5234(91)90143-b
• 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 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.58h， 生成 3-[1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxamido]propionitrile
  参考文献：
  名称：

  Efficient total syntheses of the oligopeptide antibiotics netropsin and distamycin

  摘要：

  DOI：

  10.1021/jo00220a019

文献信息

• The Synthesis of Some Head to Head Linked DNA Minor Groove Binders
  作者：Abedawn I. Khalaf、Andrew R. Pitt、Martin Scobie、Colin J. Suckling、John Urwin、Roger D. Waigh、Robert V. Fishleigh、Steven C. Young、William A. Wylie

  DOI：10.1016/s0040-4020(00)00432-4

  日期：2000.7

  A series of head to head linked dimers of heterocyclic amino acids has been prepared for investigation of affinity and selectivity in binding to the minor groove of DNA. The selection of targets for synthesis was led by computer based design. Several novel dicarboxylic acid linkers including indoles, phenanthrenes, a fluorenone, and a bisbenzothiophene have been included. Analysis of binding to DNA

  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。
• Synthesis of Geometrically Constrained Unsymmetrical Bis(polyamides) Related to the Antiviral Distamycin
  作者：Sanjay K. Sharma、Manju Tandon、J. William Lown

  DOI：10.1002/1099-0690(200006)2000:11<2095::aid-ejoc2095>3.0.co;2-j

  日期：2000.6

  for the strict DNA base-sequence recognition of (AT)4 and (AT)5, respectively, for the oligopeptide minor-groove binding agents netropsin (I) and distamycin (II) leads to proposals for the rational structure modification for altered base recognition. In this paper we report the synthesis of unsymmetrical imidazo-pyrrolo-bis(polyamides), structurally related to the natural antiviral agents distamycin

  分析分别对（AT）4和（AT）5的寡肽小沟结合剂netropsin（I）和distamycin（II）的严格DNA碱基序列识别的结构和立体化学要求导致了对合理的结构修饰，以改变碱基识别。在本文中，我们报告了与天然抗病毒剂双歧霉素在结构上相关且带有非天然（25-27）或天然（31-33）的不对称咪唑并吡咯并双（聚酰胺）的合成）由柔性或刚性接头链接的末端。这是关于在连接的双（聚酰胺）中具有二甲基氨基丙基或am基末端的带有咪唑的结构的合成的首次报道。
• Nishiwaki, Eiji; Tanaka, Shigeaki; Lee, Hideaki, Heterocycles, 1988, vol. 27, # 8, p. 1945 - 1952
  作者：Nishiwaki, Eiji、Tanaka, Shigeaki、Lee, Hideaki、Shibuya, Masayuki

  DOI：——

  日期：——
• Synthesis, DNA binding and biological evaluation of synthetic precursors and novel analogs of netropsin
  作者：Francoise Debart、Christian Perigaud、Gilles Gosselin、Driss Mrani、Bernard Rayner、Pierre Le Ber、Christian Auclair、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm00125a024

  日期：1989.5

  A series of oligopeptides have been synthesized that are structurally related to the natural agent netropsin. The binding constants to double-stranded polynucleotides as well as the cytostatic activity against both murine human tumor cell lines and the in vitro activity against a range of DNA and RNA viruses have been determined for these novel compounds and some of their synthetic precursors. 1-Methyl-5-nitropyrrole-2-carboxylic acid methyl ester (4), N-[[1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrol-2- yl]carbonyl]-L-alanine tert-butyl ester (28), and N-[[1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrol-2- yl]carbonyl]-L-alanyl-L-alanine tert-butyl ester (29) showed modest inhibitory effect on tumor cell proliferation (CD50 = 26-85 micrograms/mL). Of all the compounds that were evaluated, 28 proved the most potent antiviral agent. It was inhibitory to parainfluenza-3 virus and Coxsackie virus B4 in Vero cells at a concentration of 20 micrograms/mL.
• Synthesis of novel thiazole-containing DNA minor groove binding oligopeptides related to the antibiotic distamycin
  作者：K. Ekambareswara Rao、Yadagiri Bathini、J. William Lown

  DOI：10.1021/jo00289a057

  日期：1990.1