4-(4-methylpiperazin-1-yl)-6-(3-chloro-6-methoxyphenyl)-1,3,5-triazin-2-amine | 1620567-89-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-(4-methylpiperazin-1-yl)-6-(3-chloro-6-methoxyphenyl)-1,3,5-triazin-2-amine
• 英文别名: 4-(5-Chloro-2-methoxyphenyl)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-amine；4-(5-chloro-2-methoxyphenyl)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-amine
• CAS: 1620567-89-6
• 化学式: C₁₅H₁₉ClN₆O
• 分子量: 334.808
• InChiKey: CLLDPKOCRQKNSX-UHFFFAOYSA-N

物化性质

• 熔点：
  198-200 °C
• 沸点：
  566.259±60.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.308±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  80.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-methylpiperazin-1-yl biguanide dihydrochloride 、 5-氯-2-甲氧基苯甲酸甲酯 在 甲醇 、 sodium 作用下， 以31%的产率得到4-(4-methylpiperazin-1-yl)-6-(3-chloro-6-methoxyphenyl)-1,3,5-triazin-2-amine
  参考文献：
  名称：

  Aryl-1,3,5-triazine derivatives as histamine H4 receptor ligands

  摘要：

  A series of novel 2-amino-4-(4-methylpiperazin-1-yl)-1,3,5-triazine derivatives with different aryl substituents in the 6-position was designed, synthesized and evaluated for histamine H-4 receptor (H4R) affinity in Sf9 cells expressing human H4R co-expressed with G-protein subunits. Triazine derivative 8 with a 6-(p-chlorophenyl) substituent showed the highest affinity with hH(4)R K-i value of 203 nM and was classified as an antagonist in CAMP accumulation assay. This compound, identified as a new lead structure, demonstrated also anti-inflammatory properties in preliminary studies in mice (carrageenan-induced edema test) and neither possessed significant antiproliferative activity, nor modulated CYP3A4 activity up to concentration of 25 mu M. In order to discuss structure activity relationships molecular modeling and docking studies were undertaken. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.06.032

文献信息

• Aryl-1,3,5-triazine derivatives as histamine H4 receptor ligands
  作者：Dorota Łażewska、Małgorzata Więcek、Joanna Ner、Katarzyna Kamińska、Tim Kottke、J. Stephan Schwed、Małgorzata Zygmunt、Tadeusz Karcz、Agnieszka Olejarz、Kamil Kuder、Gniewomir Latacz、Marek Grosicki、Jacek Sapa、Janina Karolak-Wojciechowska、Holger Stark、Katarzyna Kieć-Kononowicz

  DOI：10.1016/j.ejmech.2014.06.032

  日期：2014.8

  A series of novel 2-amino-4-(4-methylpiperazin-1-yl)-1,3,5-triazine derivatives with different aryl substituents in the 6-position was designed, synthesized and evaluated for histamine H-4 receptor (H4R) affinity in Sf9 cells expressing human H4R co-expressed with G-protein subunits. Triazine derivative 8 with a 6-(p-chlorophenyl) substituent showed the highest affinity with hH(4)R K-i value of 203 nM and was classified as an antagonist in CAMP accumulation assay. This compound, identified as a new lead structure, demonstrated also anti-inflammatory properties in preliminary studies in mice (carrageenan-induced edema test) and neither possessed significant antiproliferative activity, nor modulated CYP3A4 activity up to concentration of 25 mu M. In order to discuss structure activity relationships molecular modeling and docking studies were undertaken. (C) 2014 Elsevier Masson SAS. All rights reserved.