N-(3-氨基-3-亚氨基丙基)-1-甲基-4-硝基-1H-吡咯-2-甲酰胺盐酸盐 | 24064-13-9

• 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
• 中文名称: N-(3-氨基-3-亚氨基丙基)-1-甲基-4-硝基-1H-吡咯-2-甲酰胺盐酸盐
• 英文名称: N-(3-amino-3-iminopropyl)-1-methyl-4-nitro-1H-pyrrole-2-carboxamide hydrochloride
• 英文别名: N-methyl-4-nitropyrrole-2-carboxamido-β-propionamidine hydrochloride；3-(1-methyl-4-nitropyrrole-2-carbaxamido)propionamidine hydrochloride；3-(1-methyl-4-nitropyrrole-2-carboxamido)propionamidine hydrochloride；3-(1-Methyl-4-nitropyrrole-2-carboxamido)propionamide hydrochloride；1-Methyl-4-nitro-1h-pyrrole-2-carboxylic acid 3-amino-3-iminopropyl-amide hydrochloride；N-(3-amino-3-iminopropyl)-1-methyl-4-nitropyrrole-2-carboxamide;hydrochloride
• CAS: 24064-13-9
• 化学式: C₉H₁₃N₅O₃*ClH
• 分子量: 275.695
• InChiKey: CKIRDOYTAUHLQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.41
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-氨基-3-亚氨基丙基)-1-甲基-4-硝基-1H-吡咯-2-甲酰胺盐酸盐 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 生成 N-[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]-2-[(4-amino-1-methylpyrrole-2-carbonyl)amino]-1,3-thiazole-4-carboxamide;hydrochloride
  参考文献：
  名称：

  Synthesis of novel thiazole-containing DNA minor groove binding oligopeptides related to the antibiotic distamycin

  摘要：

  DOI：

  10.1021/jo00289a057
• 作为产物：
  描述：

  N-甲基-2-吡咯羧酸 在 盐酸 、 氯化亚砜 、 (C₃H₇)2NEt 、 氨 、 硝酸 、 乙酸酐 作用下， 生成 N-(3-氨基-3-亚氨基丙基)-1-甲基-4-硝基-1H-吡咯-2-甲酰胺盐酸盐
  参考文献：
  名称：

  Synthesis, DNA binding and biological evaluation of synthetic precursors and novel analogs of netropsin

  摘要：

  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.

  DOI：

  10.1021/jm00125a024

文献信息

• Cytotoxic α-Halogenoacrylic Derivatives of Distamycin A and Congeners
  作者：Italo Beria、Pier Giovanni Baraldi、Paolo Cozzi、Marina Caldarelli、Cristina Geroni、Sergio Marchini、Nicola Mongelli、Romeo Romagnoli

  DOI：10.1021/jm031051k

  日期：2004.5.1

  action of many antitumor agents involves DNA damage, either by direct binding of the drug to DNA or to DNA-binding proteins. However, most of the DNA-interacting agents have only a limited degree of sequence specificity, which implies that they may hit all the cellular genes. DNA minor groove binders, among which the derivatives of distamycin A play an important role, could provide significant improvement

  许多抗肿瘤药的作用机制都涉及DNA损伤，这可能是由于药物与DNA或与DNA结合蛋白的直接结合而引起的。但是，大多数DNA相互作用剂仅具有有限程度的序列特异性，这意味着它们可能击中所有细胞基因。DNA小沟结合剂（其中双霉素A的衍生物起着重要作用）由于与富含胸腺嘧啶-腺嘌呤（TA）的序列具有很高的选择性，可以显着改善癌症的治疗，增加基因特异性。我们现在报告和讨论合成的，体外和体内活性以及二霉素A的α-卤代丙烯酰胺基衍生物的一些机理特征。这项工作的最终结果是选择brosTAllicin 17（PNU-166196）。BrosTAllicin，目前处于II期临床试验中，与广谱霉素衍生物塔木斯汀相比，它具有广谱的抗肿瘤活性和更高的凋亡作用。与临床测试的DNA小沟结合剂相比，brosTAllicin的重要体外毒理学特征是对人类造血祖细胞的骨髓毒性与对肿瘤细胞的细胞毒性之间的比率非常高。brosTAll
• Structure-activity relationships of pyrrole amidine antiviral antibiotics. 2. Preparation of mono- and tripyrrole derivatives of congocidine
  作者：Meir Bialer、Boris Yagen、Raphael Mechoulam、Yechiel Becker

  DOI：10.1021/jm00184a018

  日期：1980.10

  virus (HSV) replication in cultured cells, and effects on the synthesis of HS DNA in isolated nuclei in vitro, as well as on DNA synthesis by purified HSV DNA polymerase. All synthesized tripyrrole derivatives of congocidine were less cytotoxic and more active than the parent drug in all the three ant iviral tests.

  合成了三种类型的刚果金（1）类似物的代表。测试了它们的细胞毒性，在培养细胞中对单纯疱疹病毒（HSV）复制的抑制以及对离体核中HS DNA合成的影响，以及纯化HSV DNA聚合酶对DNA合成的影响。在所有三个抗病毒试验中，所有合成的刚果金三吡咯衍生物的毒性都比母体药物小，活性更高。
• Structure elucidation of a condensation product of 4-aminopyrrole derivatives and dicyclohexylcarbodiimide
  作者：Meir Bialer、Boris Yagen、Raphael Mechoulam

  DOI：10.1002/jhet.5570170834

  日期：1980.12

  The chemical structure of the two condensation products of dicyclohexylcarbodiimide (DCC) with the precursors of the mono-pyrrole homologues of distamycin and with the mono and tri-pyrrole homologues of congocidine were established. The two products isolated were proven to be condensation products between 4-aminopyrrole derivatives and dicyclohexylcarbodiimide (DCC).

  建立了二环己基碳二亚胺（DCC）与二霉素单吡咯同系物的前体以及刚果金的单吡咯和三吡咯同系物的两个缩合产物的化学结构。分离出的两种产物被证明是4-氨基吡咯衍生物与二环己基碳二亚胺（DCC）之间的缩合产物。
• Synthesis of (4S)- and (4R)-methyl 2-amino-1-pyrroline-5-carboxylate and their application to the preparation of (4S)-(+)- and (4R)-(-)-dihydrokikumycin B
  作者：Moses Lee、J. William Lown

  DOI：10.1021/jo00235a013

  日期：1987.12
• DEBART, FRANCOISE;PERIGAUD, CHRISTIAN;GOSSELIN, GILLES;MRANI, DRISS;RAYNE+, J. MED. CHEM., 32,(1989) N, C. 1074-1083
  作者：DEBART, FRANCOISE、PERIGAUD, CHRISTIAN、GOSSELIN, GILLES、MRANI, DRISS、RAYNE+

  DOI：——

  日期：——