2-chloro-N-(4-methoxybenzyl)-6-methylpyrimidin-4-amine | 512803-43-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-chloro-N-(4-methoxybenzyl)-6-methylpyrimidin-4-amine
• 英文别名: 2-chloro-N-[(4-methoxyphenyl)methyl]-6-methylpyrimidin-4-amine
• CAS: 512803-43-9
• 化学式: C₁₃H₁₄ClN₃O
• 分子量: 263.727
• InChiKey: CATPKJQFDDOVPQ-UHFFFAOYSA-N

物化性质

• 沸点：
  438.7±35.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  47
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(4-methoxybenzyl)-6-methylpyrimidin-4-amine 、 4,4'-(1,5-戊二氧基)二苯胺 在 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 0.5h， 以71%的产率得到4-N-[(4-methoxyphenyl)methyl]-2-N-[4-[5-[4-[[4-[(4-methoxyphenyl)methylamino]-6-methylpyrimidin-2-yl]amino]phenoxy]pentoxy]phenyl]-6-methylpyrimidine-2,4-diamine
  参考文献：
  名称：

  A natural product inspired hybrid approach towards the synthesis of novel pentamidine based scaffolds as potential anti-parasitic agents

  摘要：

  A natural product inspired molecular hybridization approach led us to a series of novel pentamidine based pyrimidine and chalcone scaffolds. All the hybrids were evaluated for their anti-leishmanial potential. Most of the screened compounds have showed significant in vitro anti-leishmanial activity with less cytotoxicity in comparison to the standard drugs (pentamidine, sodium stibogluconate, and miltefosine). Additionally, anti-malarial screening of these compounds was also done and four compounds have shown superior activity against chloroquine resistance strain (K1) of Plasmodium falciparum. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.101
• 作为产物：
  描述：

  2,4-二氯-6-甲基嘧啶 、 4-甲氧基苄胺 在 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-chloro-N-(4-methoxybenzyl)-6-methylpyrimidin-4-amine
  参考文献：
  名称：

  A natural product inspired hybrid approach towards the synthesis of novel pentamidine based scaffolds as potential anti-parasitic agents

  摘要：

  A natural product inspired molecular hybridization approach led us to a series of novel pentamidine based pyrimidine and chalcone scaffolds. All the hybrids were evaluated for their anti-leishmanial potential. Most of the screened compounds have showed significant in vitro anti-leishmanial activity with less cytotoxicity in comparison to the standard drugs (pentamidine, sodium stibogluconate, and miltefosine). Additionally, anti-malarial screening of these compounds was also done and four compounds have shown superior activity against chloroquine resistance strain (K1) of Plasmodium falciparum. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.101

文献信息

• Pyrimidine-Based Inhibitors of Dynamin I GTPase Activity: Competitive Inhibition at the Pleckstrin Homology Domain
  作者：Luke R. Odell、Mohammed K. Abdel-Hamid、Timothy A. Hill、Ngoc Chau、Kelly A. Young、Fiona M. Deane、Jennette A. Sakoff、Sofia Andersson、James A. Daniel、Phillip J. Robinson、Adam McCluskey

  DOI：10.1021/acs.jmedchem.6b01422

  日期：2017.1.12

  dynamin localization to the plasma membrane via the PH domain and implicate this mechanism in the inhibition of CME. We have used a computational approach of binding site identification, docking, and interaction energy calculations to design and synthesize a new library of aminopyrimidine analogues targeting site-2 of the pleckstrin homology (PH) domain. The optimized analogues showed low micromolar inhibition

  大型GTP酶动力蛋白在网格蛋白介导的内吞作用（CME）期间介导膜裂变。据报道，氨基嘧啶化合物可通过PH结构域破坏动力蛋白定位于质膜，并在抑制CME中发挥作用。我们已经使用了结合位点识别，对接和相互作用能计算的一种计算方法来设计和合成靶向pleckstrin同源性（PH）域的site-2的氨基嘧啶类似物的新文库。优化的类似物对动力蛋白I（IC 50 = 10.6±1.3至1.6±0.3μM）和CME（IC 50（CME））的微摩尔抑制作用均较低= 65.9±7.7至3.7±1.1 mM），这使该系列成为尚未报道的更有效的动力和CME抑制剂之一。在基于CME和细胞生长抑制的测定中，获得的数据与动力抑制作用一致。CEREP ExpresS分析鉴定了胆囊收缩素，多巴胺D 2，组胺H 1和H 2，黑皮质素，褪黑激素，毒蕈碱M 1和M 3，神经激肽，阿片样物质KOP和5-羟色胺受体的脱靶作用。
• A natural product inspired hybrid approach towards the synthesis of novel pentamidine based scaffolds as potential anti-parasitic agents
  作者：Vikas Tyagi、Shahnawaz Khan、Rahul Shivahare、Khushboo Srivastava、Suman Gupta、Saqib Kidwai、Kumkum Srivastava、S.K. Puri、Prem M.S. Chauhan

  DOI：10.1016/j.bmcl.2012.10.101

  日期：2013.1

  A natural product inspired molecular hybridization approach led us to a series of novel pentamidine based pyrimidine and chalcone scaffolds. All the hybrids were evaluated for their anti-leishmanial potential. Most of the screened compounds have showed significant in vitro anti-leishmanial activity with less cytotoxicity in comparison to the standard drugs (pentamidine, sodium stibogluconate, and miltefosine). Additionally, anti-malarial screening of these compounds was also done and four compounds have shown superior activity against chloroquine resistance strain (K1) of Plasmodium falciparum. (c) 2012 Elsevier Ltd. All rights reserved.