methyl (2-((5-amino-6-chloro-2-methylpyrimidin-4-yl)amino)ethyl)carbamate | 1393344-67-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: methyl (2-((5-amino-6-chloro-2-methylpyrimidin-4-yl)amino)ethyl)carbamate
• CAS: 1393344-67-6
• 化学式: C₉H₁₄ClN₅O₂
• 分子量: 259.695
• InChiKey: LOXHJXDPHQOVHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  102.16
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (2-((5-amino-6-chloro-2-methylpyrimidin-4-yl)amino)ethyl)carbamate 在 15percent FeCl₃ on SiO₂ 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 为溶剂， 生成 methyl N-[2-[8-(2-chlorophenyl)-2-methyl-6-(4-methylpiperazin-1-yl)purin-9-yl]ethyl]carbamate
  参考文献：
  名称：

  Discovery and optimization of novel purines as potent and selective CB2 agonists

  摘要：

  A focused screening strategy identified thienopyrimidine 1 as a hCB2 cannabinoid receptor agonist with moderate selectivity over the hCB1 receptor. This initial hit suffered from poor in vitro metabolic stability and high in vivo clearance. Structure-activity relationships describe the optimization and modification to a less lipophilic purine core. Examples from this novel series were found to be highly potent and fully efficacious agonists of the human CB2 receptor with excellent selectivity against CB1. Compound 10 possesses good biopharmaceutical properties, is highly water soluble and demonstrates robust oral activity in rodent models of joint pain. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.035
• 作为产物：
  描述：

  2-甲基-4,6-二氯-5-氨基嘧啶 、 N-carbomethoxyethylenediamine 以 异丙醇 为溶剂， 生成 methyl (2-((5-amino-6-chloro-2-methylpyrimidin-4-yl)amino)ethyl)carbamate
  参考文献：
  名称：

  Discovery and optimization of novel purines as potent and selective CB2 agonists

  摘要：

  A focused screening strategy identified thienopyrimidine 1 as a hCB2 cannabinoid receptor agonist with moderate selectivity over the hCB1 receptor. This initial hit suffered from poor in vitro metabolic stability and high in vivo clearance. Structure-activity relationships describe the optimization and modification to a less lipophilic purine core. Examples from this novel series were found to be highly potent and fully efficacious agonists of the human CB2 receptor with excellent selectivity against CB1. Compound 10 possesses good biopharmaceutical properties, is highly water soluble and demonstrates robust oral activity in rodent models of joint pain. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.035