(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)quinolin-6-ylamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)quinolin-6-ylamine
• 英文别名: 5-methyl-N-(quinolin-6-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine；N-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)quinolin-6-amine
• 化学式: C₁₅H₁₂N₆
• 分子量: 276.3
• InChiKey: LLCARJRNBARSBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-氨基喹啉 、 7-氯-5-甲基-1,2,4-三唑并[1,5-Alpha]嘧啶 以 乙醇 为溶剂， 生成 (5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)quinolin-6-ylamine
  参考文献：
  名称：

  Triazolopyrimidine-Based Dihydroorotate Dehydrogenase Inhibitors with Potent and Selective Activity against the Malaria Parasite Plasmodium falciparum

  摘要：

  A Plasmodium falciparum dihydroorotate dehydrogenase (PfDHODH) inhibitor that is potent (K(I) = 15 nM) and species-selective (>5000-fold over the human enzyme) was identified by high-throughput screening. The substituted triazolopyrimidine and its structural analogues were produced by an inexpensive three-step synthesis, and the series showed good association between PfDHODH inhibition and parasite toxicity. This study has identified the first nanomolar PfDHODH inhibitor with potent antimalarial activity in whole cells (EC(50) = 79 nM).

  DOI：

  10.1021/jm8001026

文献信息

• [EN] DIHYDROOROTATE DEHYDROGENASE INHIBITORS WITH SELECTIVE ANTI-MALARIAL ACTIVITY<br/>[FR] INHIBITEURS DE DIHYDROOROTATE DÉSHYDROGÉNASE PRÉSENTANT UNE ACTIVITÉ ANTIPALUDÉENNE SÉLECTIVE
  申请人：UNIV TEXAS

  公开号：WO2009082691A1

  公开（公告）日：2009-07-02

  Compounds according to Formula (I), Formula (II), Formula (III), Formula (V), Formula (VI), or to Formula (VII), and pharmaceutical compositions of compounds that conform to Formula (IV) or (Formula VIII): where R1 through R33 are prescribed, selectively inhibit P. falciparum dihydroorotate dehydrogenase. Accordingly, a method for preventing and treating malaria attaches to such compounds, as well as to pharmaceutically acceptable salts, solvates, stereoisomers, tautomers, and prodrugs thereof.

  根据公式（I），公式（II），公式（III），公式（V），公式（VI）或公式（VII）合成的化合物，以及符合公式（IV）或（公式VIII）的化合物的药物组合物，其中R1至R33被规定，选择性地抑制疟原虫脱氢鸟嘌呤酸脱氢酶。因此，一种预防和治疗疟疾的方法涉及与这些化合物以及其药用可接受的盐，溶剂化物，立体异构体，互变异构体和前药结合。
• DIHYDROOROTATE DEHYDROGENASE INHIBITORS WITH SELECTIVE ANTI-MALARIAL ACTIVITY
  申请人：PHILLIPS Margaret

  公开号：US20090209557A1

  公开（公告）日：2009-08-20

  Compounds according to Formula I, Formula II, Formula III, Formula V, Formula VI, or to Formula VII, and pharmaceutical compositions of compounds that conform to Formula IV or Formula VIII: where R 1 through R 33 are prescribed, selectively inhibit P. falciparum dihydroorotate dehydrogenase. Accordingly, a method for preventing and treating malaria attaches to such compounds, as well as to pharmaceutically acceptable salts, solvates, stereoisomers, tautomers, and prodrugs thereof.

  按照公式I，公式II，公式III，公式V，公式VI或公式VII制备的化合物和符合公式IV或公式VIII的化合物的制药组合物：其中R1到R33被规定，可以选择性地抑制P. falciparum脱氢鞘氨酸脱氢酶。因此，一种预防和治疗疟疾的方法涉及到这些化合物，以及其药学上可接受的盐，溶剂化合物，立体异构体，互变异构体和前药。
• US9216983B2
  申请人：——

  公开号：US9216983B2

  公开（公告）日：2015-12-22
• [EN] DIHYDROOROTATE DEHYDROGENASE INHIBITORS WITH SELECTIVE ANTI-MALARIAL ACTIVITY<br/>[FR] INHIBITEURS DE LA DIHYDROOROTATE DÉSHYDROGÉNASE AVEC ACTIVITÉ ANTI-MALARIQUE SÉLECTIVE
  申请人：UNIV TEXAS

  公开号：WO2007149211A1

  公开（公告）日：2007-12-27

  [EN] Pharmaceutical compositions comprising compounds of the formula (I) where R¹, R², and R³ are described here, have therapeutic utility in selectively inhibiting P. falciparum dihydroorotate dehydrogenase. Accordingly, such compositions have use in the treatment and prevention of malaria.
  [FR] L'invention concerne des compositions pharmaceutiques comprenant des composés de la formule (I), dans laquelle R¹, R², et R³ sont décrits ici, ayant une utilité thérapeutique pour inhiber sélectivement la dihydroorotate déshydrogénase de P. falciparum. En conséquence, de telles compositions ont une utilisation dans le traitement et la prévention de la malaria.
• Triazolopyrimidine-Based Dihydroorotate Dehydrogenase Inhibitors with Potent and Selective Activity against the Malaria Parasite <i>Plasmodium falciparum</i>
  作者：Margaret A. Phillips、Ramesh Gujjar、Nicholas A. Malmquist、John White、Farah El Mazouni、Jeffrey Baldwin、Pradipsinh K. Rathod

  DOI：10.1021/jm8001026

  日期：2008.6.1

  A Plasmodium falciparum dihydroorotate dehydrogenase (PfDHODH) inhibitor that is potent (K(I) = 15 nM) and species-selective (>5000-fold over the human enzyme) was identified by high-throughput screening. The substituted triazolopyrimidine and its structural analogues were produced by an inexpensive three-step synthesis, and the series showed good association between PfDHODH inhibition and parasite toxicity. This study has identified the first nanomolar PfDHODH inhibitor with potent antimalarial activity in whole cells (EC(50) = 79 nM).