3-Bromoimidazo[1,2-a]pyrazine-6-carbonyl chloride | 1607830-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡嗪类
• 英文名称: 3-Bromoimidazo[1,2-a]pyrazine-6-carbonyl chloride
• CAS: 1607830-25-0
• 化学式: C₇H₃BrClN₃O
• 分子量: 260.477
• InChiKey: CKOCTDRMXMDDBM-UHFFFAOYSA-N

物化性质

• 密度：
  2.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 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：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Bromoimidazo[1,2-a]pyrazine-6-carbonyl chloride 在 potassium fluoride 、 四(三苯基膦)钯 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 生成 N-methyl-N-(1-methylpiperidin-4-yl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide
  参考文献：
  名称：

  Lead Optimization of Imidazopyrazines: A New Class of Antimalarial with Activity onPlasmodiumLiver Stages

  摘要：

  Imidazopyridine 1 was identified from a phenotypic screen against P. falciparum (Pf) blood stages and subsequently optimized for activity on liver-stage schizonts of the rodent parasite P. yoelii (Py) as well as hypnozoites of the simian parasite P. cynomolgi (Pc). We applied these various assays to the cell-based lead optimization of the imidazopyrazines, exemplified by 3 (KAI407), and show that optimized compounds within the series with improved pharmacokinetic properties achieve causal prophylactic activity in vivo and may have the potential to target the dormant stages of P. vivax malaria.

  DOI：

  10.1021/ml500244m
• 作为产物：
  描述：

  5-氨基吡嗪-2-羧酸乙酯 在 N-溴代丁二酰亚胺(NBS) 、 草酰氯 、 碳酸氢钠 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 21.0h， 生成 3-Bromoimidazo[1,2-a]pyrazine-6-carbonyl chloride
  参考文献：
  名称：

  Lead Optimization of Imidazopyrazines: A New Class of Antimalarial with Activity onPlasmodiumLiver Stages

  摘要：

  Imidazopyridine 1 was identified from a phenotypic screen against P. falciparum (Pf) blood stages and subsequently optimized for activity on liver-stage schizonts of the rodent parasite P. yoelii (Py) as well as hypnozoites of the simian parasite P. cynomolgi (Pc). We applied these various assays to the cell-based lead optimization of the imidazopyrazines, exemplified by 3 (KAI407), and show that optimized compounds within the series with improved pharmacokinetic properties achieve causal prophylactic activity in vivo and may have the potential to target the dormant stages of P. vivax malaria.

  DOI：

  10.1021/ml500244m

文献信息

• [EN] COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF PARASITIC DISEASES<br/>[FR] COMPOSÉS ET COMPOSITIONS POUR LE TRAITEMENT DE MALADIES PARASITAIRES
  申请人：IRM LLC

  公开号：WO2014078802A1

  公开（公告）日：2014-05-22

  The present invention provides compounds of formula I: [INSERT FORMULA HERE] or a pharmaceutically acceptable salt, tautomer, or stereoisomer, thereof, wherein the variables are as defined herein. The present invention further provides pharmaceutical compositions comprising such compounds and methods of using such compounds for treating, preventing, inhibiting, ameliorating, or eradicating the pathology and/or symptomology of a disease caused by a Plasmodium parasite, such as malaria.

  本发明提供了化合物的公式I：[在此插入公式]或其药学上可接受的盐、互变异构体或立体异构体，其中变量如本文所定义。本发明还提供了包含这种化合物的药物组合物以及使用这种化合物用于治疗、预防、抑制、改善或根除由疟原虫引起的疾病的病理学和/或症状学的方法，例如疟疾。