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N-(4-(2,2,2-trifuoroethyl)phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine | 1281860-82-9

中文名称
——
中文别名
——
英文名称
N-(4-(2,2,2-trifuoroethyl)phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
英文别名
DSM214;5-methyl-N-(4-(2,2,2-trifluoroethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine;5-methyl-N-[4-(2,2,2-trifluoroethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
N-(4-(2,2,2-trifuoroethyl)phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine化学式
CAS
1281860-82-9
化学式
C14H12F3N5
mdl
——
分子量
307.278
InChiKey
XBIVLGNMWGHHLL-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 密度:
    1.42±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    3.7
  • 重原子数:
    22
  • 可旋转键数:
    3
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.21
  • 拓扑面积:
    55.1
  • 氢给体数:
    1
  • 氢受体数:
    7

反应信息

  • 作为产物:
    参考文献:
    名称:
    Lead Optimization of Aryl and Aralkyl Amine-Based Triazolopyrimidine Inhibitors of Plasmodium falciparum Dihydroorotate Dehydrogenase with Antimalarial Activity in Mice
    摘要:
    Malaria is one of the leading causes of severe infectious disease worldwide; yet, our ability to maintain effective therapy to combat the illness is continually challenged by the emergence of drug resistance. We previously reported identification of a new class of triazolopyrimidine-based Plasmodium falciparum dihydroorotate dehydrogenase (PfDHODH) inhibitors with antimalarial activity, leading to the discovery of a new lead series and novel target for drug development. Active compounds from the series contained a triazolopyrimidine ring attached to an aromatic group through a bridging nitrogen atom. Herein, we describe systematic efforts to optimize the aromatic functionality with the goal of improving potency and in vivo properties of compounds from the series. These studies led to the identification of two new substituted aniline moieties (4-SF(5)-Ph and 3,5-Di-F-4-CF(3)-Ph), which, when coupled to the triazolopyrimidine ring, showed good plasma exposure and better efficacy in the Plasmodium berghei mouse model of the disease than previously reported compounds from the series.
    DOI:
    10.1021/jm200265b
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文献信息

  • ANTIMALARIAL AGENTS THAT ARE INHIBITORS OF DIHYDROOROTATE DEHYDROGENASE
    申请人:Rathod Pradipsinh K.
    公开号:US20120302586A1
    公开(公告)日:2012-11-29
    Inhibitors of parasitic dihydroorotate dehydrogenase enzyme (DHOD) are candidate therapeutics for treating malaria. Illustrative of such therapeutic agents include the compound: and a triazolopyrimidine class of compounds that conform to Formula IX: and their solvates, stereoisomers, tautomers and pharmaceutically acceptable salts.
    抑制寄生虫脱氢酶酶(DHOD)的药物是治疗疟疾的候选治疗药物。这类治疗药物的例子包括化合物:以及符合公式IX的三唑嘧啶类化合物及其溶剂化物、立体异构体、互变异构体和药学上可接受的盐。
  • US9238653B2
    申请人:——
    公开号:US9238653B2
    公开(公告)日:2016-01-19
  • [EN] ANTIMALARIAL AGENTS THAT ARE INHIBITORS OF DIHYDROOROTATE DEHYDROGENASE<br/>[FR] AGENTS ANTIPALUDIQUES INHIBITEURS DE LA DIHYDRO-OROTATE DÉSHYDROGÉNASE
    申请人:UNIV TEXAS
    公开号:WO2011041304A2
    公开(公告)日:2011-04-07
    Inhibitors of parasitic dihydroorotate dehydrogenase enzyme (DHOD) are candidate therapeutics for treating malaria. Illustrative of such therapeutic agents include the compound: and a triazolopyrimidine class of compounds that conform to Formula (IX): and their solvates, stereoisomers, tautomers and pharmaceutically acceptable salts.
  • Lead Optimization of Aryl and Aralkyl Amine-Based Triazolopyrimidine Inhibitors of <i>Plasmodium falciparum</i> Dihydroorotate Dehydrogenase with Antimalarial Activity in Mice
    作者:Ramesh Gujjar、Farah El Mazouni、Karen L. White、John White、Sharon Creason、David M. Shackleford、Xiaoyi Deng、William N. Charman、Ian Bathurst、Jeremy Burrows、David M. Floyd、David Matthews、Frederick S. Buckner、Susan A. Charman、Margaret A. Phillips、Pradipsinh K. Rathod
    DOI:10.1021/jm200265b
    日期:2011.6.9
    Malaria is one of the leading causes of severe infectious disease worldwide; yet, our ability to maintain effective therapy to combat the illness is continually challenged by the emergence of drug resistance. We previously reported identification of a new class of triazolopyrimidine-based Plasmodium falciparum dihydroorotate dehydrogenase (PfDHODH) inhibitors with antimalarial activity, leading to the discovery of a new lead series and novel target for drug development. Active compounds from the series contained a triazolopyrimidine ring attached to an aromatic group through a bridging nitrogen atom. Herein, we describe systematic efforts to optimize the aromatic functionality with the goal of improving potency and in vivo properties of compounds from the series. These studies led to the identification of two new substituted aniline moieties (4-SF(5)-Ph and 3,5-Di-F-4-CF(3)-Ph), which, when coupled to the triazolopyrimidine ring, showed good plasma exposure and better efficacy in the Plasmodium berghei mouse model of the disease than previously reported compounds from the series.
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