2-amino-6-(3-methylphenyl)pyrimidine-4-carboxylic acid | 863548-73-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-amino-6-(3-methylphenyl)pyrimidine-4-carboxylic acid
• 英文别名: 4-Pyrimidinecarboxylic acid,2-amino-6-(3-methylphenyl)-
• CAS: 863548-73-6
• 化学式: C₁₂H₁₁N₃O₂
• 分子量: 229.238
• InChiKey: WTEBBYHRAXZIGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  89.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-6-(3-methylphenyl)pyrimidine-4-carboxylic acid 、 2-氨基甲基-3-甲基吡啶 在 polymer supported carbodiimide 、 1-羟基苯并三唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以42%的产率得到N-((3-methyl-pyridin-2-yl)methyl)-2-amino-6-(meta-tolyl)pyrimidine-4-carboxamide
  参考文献：
  名称：

  Antagonists of the human A2A receptor. Part 6: Further optimization of pyrimidine-4-carboxamides

  摘要：

  Antagonists of the human A(2A) receptor have been reported to have potential therapeutic benefit in the alleviation of the symptoms associated with neurodegenerative movement disorders such as Parkinson's disease. As part of our efforts to discover potent and selective antagonists of this receptor, we herein describe the detailed optimization and structure-activity relationships of a series of pyrimidine-4-carboxamides. These optimized derivatives display desirable physiochemical and pharmacokinetic profiles, which have led to promising oral activity in clinically relevant models of Parkinson's disease. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.078
• 作为产物：
  描述：

  在 水 、 lithium hydroxide 、 盐酸 作用下， 反应 2.0h， 生成 2-amino-6-(3-methylphenyl)pyrimidine-4-carboxylic acid
  参考文献：
  名称：

  Antagonists of the human A2A receptor. Part 6: Further optimization of pyrimidine-4-carboxamides

  摘要：

  Antagonists of the human A(2A) receptor have been reported to have potential therapeutic benefit in the alleviation of the symptoms associated with neurodegenerative movement disorders such as Parkinson's disease. As part of our efforts to discover potent and selective antagonists of this receptor, we herein describe the detailed optimization and structure-activity relationships of a series of pyrimidine-4-carboxamides. These optimized derivatives display desirable physiochemical and pharmacokinetic profiles, which have led to promising oral activity in clinically relevant models of Parkinson's disease. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.078

文献信息

• Pyrimidine Compounds as Purine Receptor Antagonist
  申请人：Gillespie John Roger

  公开号：US20070281936A1

  公开（公告）日：2007-12-06

  Compounds of formula (I); wherein R 1 is H or NHZ; R 2 is optionally substituted aryl or heteroaryl attached via a carbon atom; R 3 is H; optionally substituted C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, or C 3 C 7 cycloalkyl, halogen; OH or OR, or R 4 is H, optionally substituted C 1 -C 6 alkyl, C 3 C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 7 cycloalkyl, aryl or heteroaryl, R 5 is H or optionally substituted C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, or C 3 -C 7 cycloalkyl; or R 4 and R 5 together form a 5 or 6-membered heterocyclic ring; and R 10 is optionally substituted C 1 -C 6 alkyl; are purine receptor, particularly adenosine receptor antagonists, useful for treatment of, inter alia, movement disorders such as Parkinsons disease.

  化合物的公式（I）;其中R1是H或NHZ; R2是通过碳原子连接的可选取代芳基或杂环芳基; R3是H; 可选取代的C1-C6烷基，C2-C6烯基，C2-C6炔基或C3C7环烷基，卤素; OH或OR，或R4是H，可选取代的C1-C6烷基，C3C6烯基，C3-C6炔基，C3-C7环烷基，芳基或杂环芳基，R5是H或可选取代的C1-C6烷基，C3-C6烯基，C3-C6炔基或C3-C7环烷基; 或R4和R5一起形成5或6元杂环环; R10是可选取代的C1-C6烷基; 是嘌呤受体，特别是腺苷受体拮抗剂，用于治疗运动障碍，如帕金森病等。
• PYRIMIDINE COMPOUNDS AS PURINE RECEPTOR ANTAGONIST
  申请人：VERNALIS (R&D) LTD

  公开号：EP1720553A1

  公开（公告）日：2006-11-15
• US7875600B2
  申请人：——

  公开号：US7875600B2

  公开（公告）日：2011-01-25
• [EN] PYRIMIDINE COMPOUNDS AS PURINE RECEPTOR ANTAGONIST<br/>[FR] COMPOSES DE PYRIMIDINE UTILISES COMME ANTAGONISTE DES RECEPTEURS DE LA PURINE
  申请人：VERNALIS R & D LTD

  公开号：WO2005079801A1

  公开（公告）日：2005-09-01

  Compounds of formula (I); wherein R1 is H or NHZ; R2 is optionally substituted aryl or heteroaryl attached via a carbon atom; R3 is H; optionally substituted C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, or C3­ C7 cycloalkyl, halogen; OH or OR,or R4 is H, optionally substituted C1-C6alkyl, C3­ C6alkenyl, C3-C6alkynyl, C3-C7 cycloalkyl, aryl or heteroaryl, R5 is H or optionally substituted C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, or C3-C7 cycloalkyl; or R4 and R5 together form a 5 or 6-membered heterocyclic ring; and R10 is optionally substituted C1-C6alkyl; are purine receptor, particularly adenosine receptor antagonists, useful for treatment of, inter alia, movement disorders such as Parkinsons disease.
• Antagonists of the human A2A receptor. Part 6: Further optimization of pyrimidine-4-carboxamides
  作者：Roger J. Gillespie、Samantha J. Bamford、Alex Clay、Suneel Gaur、Tim Haymes、Philip S. Jackson、Allan M. Jordan、Burkhard Klenke、Stefania Leonardi、Jeanette Liu、Howard L. Mansell、Sean Ng、Mona Saadi、Heather Simmonite、Gemma C. Stratton、Richard S. Todd、Douglas S. Williamson、Ian A. Yule

  DOI：10.1016/j.bmc.2009.07.078

  日期：2009.9

  Antagonists of the human A(2A) receptor have been reported to have potential therapeutic benefit in the alleviation of the symptoms associated with neurodegenerative movement disorders such as Parkinson's disease. As part of our efforts to discover potent and selective antagonists of this receptor, we herein describe the detailed optimization and structure-activity relationships of a series of pyrimidine-4-carboxamides. These optimized derivatives display desirable physiochemical and pharmacokinetic profiles, which have led to promising oral activity in clinically relevant models of Parkinson's disease. (C) 2009 Elsevier Ltd. All rights reserved.