6-chloro-5-nitro-N-phenylpyrimidin-4-amine | 500200-53-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 6-chloro-5-nitro-N-phenylpyrimidin-4-amine
• 英文别名: 6-Anilino-4-chloro-5-nitropyrimidine
• CAS: 500200-53-3
• 化学式: C₁₀H₇ClN₄O₂
• 分子量: 250.644
• InChiKey: ADUILKHYQAXJRT-UHFFFAOYSA-N

物化性质

• 沸点：
  410.3±45.0 °C(Predicted)
• 密度：
  1.512±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-chloro-5-nitro-N-phenylpyrimidin-4-amine 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 6-N-methyl-5-nitroso-4-N-phenylpyrimidine-4,6-diamine
  参考文献：
  名称：

  Transformation of methyl N-methyl-N-(6-substituted-5-nitro-4-pyrimidinyl)aminoacetates into 4-methylamino-5-nitrosopyrimidines and 9-methylpurin-8-ones

  摘要：

  N-Methyl-N-(6-substituted-5-nitro-4-pyrimidinyl)aminoacetic acid methyl esters under the treatment of sodium alkoxides, depending on the nature of substituents in 6 position of the pyrimidine ring, undergo ring closure and rearrangement to give 6-substituted-4-methylamino-5-nitrosopyrimidines or 9-meth ylpurin-8 -ones. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.119
• 作为产物：
  描述：

  4,6-二氯-5-硝基嘧啶 、 苯胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 作用下， 以 甲苯 为溶剂， 反应 3.5h， 以49.6%的产率得到6-chloro-5-nitro-N-phenylpyrimidin-4-amine
  参考文献：
  名称：

  氯取代的5-硝基嘧啶与胺的钯催化胺化

  摘要：

  摘要开发了一种简洁高效的方法，通过钯催化氯取代的5-硝基嘧啶和胺的胺化反应合成单取代和二取代的嘧啶产品。这种合成方法可以高产率地生产具有良好官能团耐受性的各种二取代的嘧啶，并为合成具有生物活性的核苷和嘌呤的重要中间体提供了补充工具。

  DOI：

  10.1016/j.cclet.2016.11.019

文献信息

• Compounds containing a N-heteroaryl moiety linked to fused ring moieties for the inhibition of NAD(P)H oxidases and platelet activation
  申请人：Vasopharm Biotech GmbH

  公开号：EP1598354A1

  公开（公告）日：2005-11-23

  The invention relates to compounds containing a N-heteroaryl moiety, which is linked via oxygen, sulfur or nitrogen, or via a methylene bridge and oxygen, sulfur or nitrogen to a fused ring moiety, in particular to the 1,2,3-triazolo[4,5-d]pyrimidine-7-yl radical. The invention also relates to a process for the preparation of said compounds and the use thereof in drugs for the treatment of NAD(P)H oxidases-related diseases and disorders and inhibition of platelet activation.

  该发明涉及含有N-杂环芳基团的化合物，该化合物通过氧、硫或氮，或通过亚甲基桥和氧、硫或氮连接到融合环基团，特别是到1,2,3-三唑并[4,5-d]嘧啶-7-基自由基。该发明还涉及一种制备所述化合物的方法以及在治疗NAD(P)H氧化酶相关疾病和疾病以及抑制血小板活化的药物中的使用。
• [EN] COMPOUNDS CONTAINING A N-HETEROARYL MOIETY LINKED TO FUSED RING MOIETIES FOR THE INHIBITION OF NAD(P)H OXIDASES AND PLATELET ACTIVATION<br/>[FR] COMPOSES COMPRENANT UNE FRACTION N-HETEROARYLE LIEE A DES FRACTIONS DE NOYAU FUSIONNEES ET DESTINES A L'INHIBITION DES NAD(P)H OXYDASES ET DE L'ACTIVATION DE PLAQUETTES
  申请人：VASOPHARM BIOTECH GMBH

  公开号：WO2005111041A1

  公开（公告）日：2005-11-24

  The invention relates to compounds containing a N-heteroaryl moiety, which is linked via oxygen, sulfur or nitrogen, or via a methylene bridge and oxygen, sul­fur or nitrogen to a fused ring moiety, in particular to the 1,2,3-triazolo[4,5­d]pyrimidine-7-yl radical. The invention also relates to a process for the prepara­tion of said compounds and the use thereof in drugs for the treatment of NAD(P)H oxidases-related diseases and disorders and inhibition of platelet activation.

  本发明涉及一种含有N-杂芳基基团的化合物，该基团通过氧、硫或氮或通过亚甲基桥和氧、硫或氮连接到融合环基团上，特别是1,2,3-三唑并[4,5-d]嘧啶-7-基自由基。本发明还涉及制备该化合物的方法以及在治疗NAD（P）H氧化酶相关疾病和障碍以及抑制血小板活化的药物中使用该化合物的用途。
• Compounds Containing a N-Heteroaryl Moiety Linked to Fused Ring Moieties for the Inhibition of Nad(P)H Oxidases and Platelet Activation
  申请人：Tegtmeier Frank

  公开号：US20080044354A1

  公开（公告）日：2008-02-21

  The invention relates to compounds containing a N-heteroaryl moiety, which is linked via oxygen, sulfur or nitrogen, or via a methylene bridge and oxygen, sulfur or nitrogen to a fused ring moiety, in particular to the 1,2,3-triazolo[4,5d]pyrimidine-7-yl radical. The invention also relates to a process for the preparation of said compounds and the use thereof in drugs for the treatment of NAD(P)H oxidases-related diseases and disorders and inhibition of platelet activation.

  该发明涉及含有N-杂环芳基基团的化合物，该基团通过氧、硫或氮或通过亚甲基桥和氧、硫或氮连接到一个融合环基团上，特别是1,2,3-三唑并[4,5d]嘧啶-7-基自由基。该发明还涉及制备该化合物的方法以及在治疗NAD（P）H氧化酶相关疾病和障碍以及抑制血小板活化的药物中使用它们的用途。
• Discovery and structure–activity analysis of 4-((5-nitropyrimidin-4-yl)amino)benzimidamide derivatives as novel protein arginine methyltransferase 1 (PRMT1) inhibitors
  作者：Xu-Ri Yu、Yun Tang、Wen-Jing Wang、Sen Ji、Shuang Ma、Lei Zhong、Chun-Hui Zhang、Jiao Yang、Xiao-Ai Wu、Zheng-Yan Fu、Lin-Li Li、Sheng-Yong Yang

  DOI：10.1016/j.bmcl.2015.06.095

  日期：2015.11

  Despite a potential application of PRMT1 inhibitors in cancer treatment, very few of PRMT1 inhibitors have been reported. To obtain novel potent PRMT1 inhibitors, structure optimizations towards a hit compound, 4-((6-chloro-5-nitropyrimidin-4-yl)amino)benzimidamide, were carried out. A series of 4-((5-nitropyrimidin-4-yl)amino)benzimidamide derivatives were synthesized. Structure-activity relationship analysis led to the discovery of a number of PRMT1 inhibitors. The most potent compound corresponds to compound 6d, which showed an IC50 value of 2.0 mu M against PRMT1. This compound also displayed a considerable anti-proliferative activity against three tumor cell lines, DLD-1, T24 and SH-SY-5Y, with IC50 values of 4.4 mu M, 13.1 mu M and 11.4 mu M, respectively. (C) 2015 Elsevier Ltd. All rights reserved.
• Highly polarized enamines. 2. Synthesis and investigation of the further amination of derivatives of ?,?-DIAMINO-?-cyano-?-nitroethylene
  作者：V. A. Makarov、A. L. Sedov、O. S. Anisimova、V. G. Granik

  DOI：10.1007/bf01164870

  日期：1996.6