1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)-pyrrole-2-carboxamidopropionamidine | 6576-40-5

• 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: 1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)-pyrrole-2-carboxamidopropionamidine
• 英文别名: 3-<1-Methyl-4-(1-methyl-4-amino-pyrrol-(2)-carboxamido)-2-pyrrolcarboxamido>-propionamidin；1-Methyl-4-<1-methyl-4-aminopyrrolyl-(2)-carbonylamino>-pyrrol-(2)-carbonsaeure-N-<2-amidino-ethyl>-amid；4-amino-N-[5-[(3-amino-3-imino-propyl)carbamoyl]-1-methyl-pyrrol-3-yl]-1-methyl-pyrrole-2-carboxamide；4-amino-N-[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]-1-methylpyrrole-2-carboxamide
• CAS: 6576-40-5
• 化学式: C₁₅H₂₁N₇O₂
• 分子量: 331.377
• InChiKey: JKQDWVURPXBPFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  144
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(5-Yl-pentanoate)-7,10,12-trimethyl-6-H-<1,3>-oxazolo-<5,4-c>-pyrido-<3,4-g>-carbazole 、 1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)-pyrrole-2-carboxamidopropionamidine 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以32%的产率得到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>pyrrole-2-carboxamido)propionamidine bis-(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：

  N-(3-amino-3-iminopropyl)-1-methyl-4-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrole-2-carboxamide hydrochloride 在 palladium on activated charcoal 氢气 作用下， 以 异丙醇 为溶剂， 生成 1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)-pyrrole-2-carboxamidopropionamidine
  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

• Antimicrobial Lexitropsins Containing Amide, Amidine, and Alkene Linking Groups
  作者：Nahoum G. Anthony、David Breen、Joanna Clarke、Gavin Donoghue、Allan J. Drummond、Elizabeth M. Ellis、Curtis G. Gemmell、Jean-Jacques Helesbeux、Iain S. Hunter、Abedawn I. Khalaf、Simon P. Mackay、John A. Parkinson、Colin J. Suckling、Roger D. Waigh

  DOI：10.1021/jm070831g

  日期：2007.11.1

  -resistant strains, in the range of 0.1-5 microg mL-1, which is comparable to many established antibacterial agents. Antifungal activity was also found in the range of 20-50 microg mL-1 MIC against Aspergillus niger and Candida albicans, again comparable with established antifungal drugs. A quinoline derivative was found to protect mice against S. aureus infection for a period of up to six days after a single

  描述了80种与二霉素和噻唑类相关的短小沟结合剂的合成和性能。化合物的设计主要基于小沟结合剂和DNA之间的疏水相互作用而增加的亲和力。疏水性芳族头基（包括喹啉基和苯甲酰基衍生物）的引入以及烯烃作为连接剂的引入，导致几种具有MIC的金黄色葡萄球菌的强活性抗菌化合物（对甲氧西林敏感和耐药的菌株）范围为0.1-5 microg mL -1，与许多已建立的抗菌剂相当。还发现针对黑曲霉和白色念珠菌的抗真菌活性为20-50微克mL-1 MIC，再次与已确立的抗真菌药物相当。
• Process for the synthesis of distamycin and derivatives thereof using 1-methyl-4-formylamino-2-pyrrolecarbonyl chloride iteratively as an intermediate
  申请人：Lombardi Paolo

  公开号：US20070060523A1

  公开（公告）日：2007-03-15

  A process for the total synthesis of Distamycin, and synthetic poly-(4aminopyrrole-2-carboxamide) congeners thereof, using 1-methyl-4-forinylamino-2-pyrrolecarbonyl chloride iteratively as an intermediate, is provided. The process finds application for both in solution and solid support synthetic technologies.

  本发明提供了一种使用1-甲基-4-吡啶基甲酰氯作为中间体，迭代地进行Distamycin的全合成以及其合成的聚（4-氨基吡咯-2-羧酰胺）类似物的方法。该方法适用于溶液和固相合成技术。
• Synthesis, determination of sequence selective DNA minor groove binding and biological evaluation of hybrid bithiazole-linked netropsin derivatives
  作者：D Mrani、G Gosselin、C Bailly、R Houssin、KE Rao、J Zimmermann、J Balzarini、E De Clercq、JP Hénichart、JL Imbach、JW Lown

  DOI：10.1016/0223-5234(92)90146-r

  日期：1992.6

  A series of hybrid molecules have been synthesized which result from the combination of a DNA sequence-specific ligand (netropsin) coupled to a DNA-interactive structural component of bleomycins (bithiazole). The DNA binding affinities as well as the cytostatic activity and their in vitro activity against a wide variety of viruses have been determined. Most of the new agents retain the DNA binding capacity of netropsin and distamycin, and force field and Pi calculations reveal the important role of the arc of curvature of these compounds in their binding to DNA. Like netropsin, the evaluated molecules did not show significant antiviral activity, but one of them demonstrated enhanced cytostatic activity against both human and murine tumor cell lines.
• DISTAMYCIN A ANALOGUES AS ANTITUMOUR OR ANTIVIRAL AGENTS
  申请人：Pharmacia Italia S.p.A.

  公开号：EP0722446B1

  公开（公告）日：2002-12-11
• US7449547B2
  申请人：——

  公开号：US7449547B2

  公开（公告）日：2008-11-11