ethyl 3-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyrazine-6-carboxylate | 1607830-85-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 3-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyrazine-6-carboxylate
• 英文别名: Ethyl 3-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyrazine-6-carboxylate；ethyl 3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxylate
• CAS: 1607830-85-2
• 化学式: C₁₆H₁₂F₃N₃O₂
• 分子量: 335.285
• InChiKey: JCQFDBYPMYBJJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 3-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyrazine-6-carboxylate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以55%的产率得到3-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyrazine-6-carboxylic acid
  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：

  ethyl pyrrolo[1,2-a]pyrazine-3-carboxylate 在 potassium fluoride 、 N-溴代丁二酰亚胺(NBS) 、 三(邻甲基苯基)磷 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 3.2h， 生成 ethyl 3-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyrazine-6-carboxylate
  参考文献：
  名称：

  [EN] COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF PARASITIC DISEASES
  [FR] COMPOSÉS ET COMPOSITIONS POUR LE TRAITEMENT DE MALADIES PARASITAIRES

  摘要：

  本发明提供了式I的化合物：[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治疗、预防、抑制、改善或根除由疟原虫引起的疟疾等疾病的方法。

  公开号：

  WO2014078813A1

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：WO2014078813A1

  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, such as malaria, caused by a Plasmodium parasite.

  本发明提供了式I的化合物：[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治疗、预防、抑制、改善或根除由疟原虫引起的疟疾等疾病的方法。
• COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF PARASITIC DISEASES
  申请人：CHATTERJEE Arnab Kumar

  公开号：US20150291598A1

  公开（公告）日：2015-10-15

  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, such as malaria, caused by a Plasmodium parasite.

  本发明提供了I式化合物：[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，其中变量的定义如本文所述。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治疗、预防、抑制、改善或根除由疟原虫引起的疾病，如疟疾的病理学和/或症状学的方法。
• QUINOLINE INHIBITORS OF TYROSINE KINASE
  申请人：Zhang Chengzhi

  公开号：US20110195066A1

  公开（公告）日：2011-08-11

  The present invention relates to new quinoline inhibitors of tyrosine kinases, pharmaceutical compositions thereof, and methods of use thereof.
• TRIMETHOXYPHENYL INHIBITORS OF TYROSINE KINASE
  申请人：Zhang Chengzhi

  公开号：US20110206661A1

  公开（公告）日：2011-08-25

  The present invention relates to new trimethoxyphenyl inhibitors of tyrosine kinase, pharmaceutical compositions thereof, and methods of use thereof.
• Lead Optimization of Imidazopyrazines: A New Class of Antimalarial with Activity on<i>Plasmodium</i>Liver Stages
  作者：Bin Zou、Advait Nagle、Arnab K. Chatterjee、Seh Yong Leong、Liying Jocelyn Tan、Wei Lin Sandra Sim、Pranab Mishra、Prasuna Guntapalli、David C. Tully、Suresh B. Lakshminarayana、Chek Shik Lim、Yong Cheng Tan、Siti Nurdiana Abas、Christophe Bodenreider、Kelli L. Kuhen、Kerstin Gagaring、Rachel Borboa、Jonathan Chang、Chun Li、Thomas Hollenbeck、Tove Tuntland、Anne-Marie Zeeman、Clemens H. M. Kocken、Case McNamara、Nobutaka Kato、Elizabeth A. Winzeler、Bryan K. S. Yeung、Thierry T. Diagana、Paul W. Smith、Jason Roland

  DOI：10.1021/ml500244m

  日期：2014.8.14

  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.