2-(trifluoromethyl)pyrido[2,3-b]pyrazin-3-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶吡嗪类
• 英文名称: 2-(trifluoromethyl)pyrido[2,3-b]pyrazin-3-ol
• 英文别名: 2-(trifluoromethyl)pyrido[2,3-b]pyrazin-3(4H)-one；2-(trifluoromethyl)-4H-pyrido[2,3-b]pyrazin-3-one
• 化学式: C₈H₄F₃N₃O
• 分子量: 215.134
• InChiKey: BCFPZJRDESOERP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(trifluoromethyl)pyrido<2,3-b>pyrazin-2-one 、 2-(trifluoromethyl)pyrido[2,3-b]pyrazin-3-ol 、 2-chloro-3-(trifluoromethyl)pyrido[2,3-b]pyrazine 在 ice 、 乙酸乙酯 、 Sodium sulfate-III 、 crude compound 、 silica gel 作用下， 以 三氯氧磷 为溶剂， 反应 2.0h， 生成 3-chloro-2-(trifluoromethyl)pyrido[2,3-b]pyrazine
  参考文献：
  名称：

  Hepatitis C Virus Inhibitors

  摘要：

  公开了具有一般式(I)的丙型肝炎病毒抑制剂。还公开了包含该化合物的组合物和使用该化合物抑制丙型肝炎病毒的方法。

  公开号：

  US20140127156A1
• 作为产物：
  描述：

  2,3-二氨基吡啶 、 3,3,3-三氟丙酮酸乙酯 以 乙醇 为溶剂， 反应 16.0h， 生成 3-(trifluoromethyl)pyrido<2,3-b>pyrazin-2-one 、 2-(trifluoromethyl)pyrido[2,3-b]pyrazin-3-ol
  参考文献：
  名称：

  Hepatitis C virus inhibitors

  摘要：

  揭示了具有一般式（I）的丙型肝炎病毒抑制剂。还公开了包含这些化合物的组合物和使用这些化合物抑制HCV的方法。

  公开号：

  US09643999B2

文献信息

• Fluorine-19 NMR studies on the mechanism of riboflavin synthase. Synthesis of 6-(trifluoromethyl)-7-oxo-8-(D-ribityl)lumazine and 6-(trifluoromethyl)-7-methyl-8-(D-ribityl)lumazine
  作者：Mark Cushman、Hemantkumar H. Patel、Johannes Scheuring、Adelbert Bacher

  DOI：10.1021/jo00047a015

  日期：1992.10

  The reactions of hexafluoropropene oxide (19), methyl trifluoropyruvate (21), and 1,1,1-trifluorobutane-2,3-dione (45) with a series of ortho diamines were investigated as an approach to the synthesis of trifluoromethyl-substituted quinoxalinones and lumazines. 6-(Trifluoromethyl)-7-oxo-8-(D-ribityl)lumazine (11) was synthesized by reaction of methyl trifluoropyruvate (21) with 5-amino-6-(D-ribitylamino)-2,4(1H,3H)-pyrimidinedione (3) hydrochloride and utilized as a F-19 NMR probe of the light riboflavin synthase of Bacillus subtilis. The fluorolumazine 11 was found to be an inhibitor of the enzyme with an inhibition constant K(I) = 55 muM. Equilibrium dialysis experiments indicated the binding of six molecules of 11 per enzyme molecule, corresponding to one molecule bound at each of the three donor and three acceptor sites of the enzyme. The apparent dissociation constants K(D) were approximately 4 and 112 muM. The enzyme-bound ligand gave rise to several broad F-19 NMR signals which were shifted to low field. The bound ligand 11 could be displaced from the enzyme by the enzyme product, riboflavin (2), and the product analog, 5-nitroso-6-(ribitylamino)-2,4(1H,3H)-pyrimidinedione (56). 6-(Trifluoromethyl)-7-methyl-8-(D-ribityl)lumazine (13) was synthesized by reaction of the hydrochloride salt of 3 with 1,1,1-trifluorobutane-2,3-dione (45). Three molecules of 13 can be bound relatively tightly per mole of riboflavin synthase, i.e., one ligand molecule per protein subunit. The inhibition constant K(I) was determined to be 75 muM, while dissociation constants of 17 and 70 muM were determined by equilibrium dialysis and F-19 NMR, respectively. The bound ligand 13 could also be displaced by riboflavin and product analog 56. A scheme for the catalytic cycle of riboflavin synthase is proposed.
• HEPATITIS C VIRUS INHIBITORS
  申请人：Bristol-Myers Squibb Company

  公开号：EP2914615A1

  公开（公告）日：2015-09-09
• US9643999B2
  申请人：——

  公开号：US9643999B2

  公开（公告）日：2017-05-09
• [EN] HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2014071032A1

  公开（公告）日：2014-05-08

  Hepatitis C virus inhibitors having the general formula (I), are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
• Hepatitis C virus inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US09643999B2

  公开（公告）日：2017-05-09

  Hepatitis C virus inhibitors having the general formula (I) are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

  揭示了具有一般式（I）的丙型肝炎病毒抑制剂。还公开了包含这些化合物的组合物和使用这些化合物抑制HCV的方法。