6-乙炔基咪唑并[1,2-A]吡嗪 | 1372096-41-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡嗪类
• 中文名称: 6-乙炔基咪唑并[1,2-A]吡嗪
• 英文名称: 6-ethynylimidazolo[1,2-A]pyrazine
• 英文别名: 6-Ethynylimidazo[1,2-a]pyrazine；6-ethynylimidazo[1,2-a]pyrazine
• CAS: 1372096-41-7
• 化学式: C₈H₅N₃
• 分子量: 143.148
• InChiKey: ALNLKKWQOAJCJY-UHFFFAOYSA-N

物化性质

• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

反应信息

• 作为反应物：
  描述：

  6-溴-N-(3-氯-4-((3-氟苄基)氧基)苯基)噻吩并[3,2-d]嘧啶-4-胺 、 6-乙炔基咪唑并[1,2-A]吡嗪 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以13%的产率得到N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(imidazo[1,2-a]pyrazin-6-ylethylnyl)thieno[3,2-d]pyrimidin-4-amine
  参考文献：
  名称：

  Series of Alkynyl-Substituted Thienopyrimidines as Inhibitors of Protozoan Parasite Proliferation

  摘要：

  Discovery of new chemotherapeutic lead agents can be accelerated by optimizing chemotypes proven to be effective in other diseases to act against parasites. One such medicinal chemistry campaign has focused on optimizing the anilinoquinazoline drug lapatinib (1) and the alkynyl thieno[3,2-d]pyrimidine hit GW837016X (NEU-391, 3) into leads for antitrypanosome drugs. We now report the structure activity relationship studies of 3 and its analogs against Trypanosoma brucei, which causes human African trypanosomiasis (HAT). The series was also tested against Trypanosoma cruzi, Leishmania major, and Plasmodium falciparum. In each case, potent antiparasitic hits with acceptable toxicity margins over mammalian HepG2 and NIH3T3 cell lines were identified. In a mouse model of HAT, 3 extended life of treated mice by 50%, compared to untreated controls. At the cellular level, 3 inhibited mitosis and cytokinesis in T. brucei. Thus, the alkynylthieno[3,2-d]pyrimidine chemotype is an advanced hit worthy of further optimization as a potential chemotherapeutic agent for HAT.

  DOI：

  10.1021/acsmedchemlett.8b00245