2-isopropyl-6-(5-methyl-2-furyl)pyrimidine-4-carbonitrile | 863495-55-0

• 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-isopropyl-6-(5-methyl-2-furyl)pyrimidine-4-carbonitrile
• 英文别名: 6-(5-Methylfuran-2-yl)-2-propan-2-ylpyrimidine-4-carbonitrile
• CAS: 863495-55-0
• 化学式: C₁₃H₁₃N₃O
• 分子量: 227.266
• InChiKey: YVVQAOLWQGEKPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-isopropyl-6-(5-methyl-2-furyl)pyrimidine-4-carbonitrile 在 硫酸 、 水 作用下， 反应 2.0h， 生成 2-isopropyl-6-(5-methyl-2-furyl)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
• 作为产物：
  描述：

  sodium cyanide 、 4-chloro-6-(5-methyl-2-furyl)-2-isopropylpyrimidine 在 三乙烯二胺 作用下， 以 二甲基亚砜 为溶剂， 反应 144.0h， 生成 2-isopropyl-6-(5-methyl-2-furyl)pyrimidine-4-carbonitrile
  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

• [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：WO2005079800A1

  公开（公告）日：2005-09-01

  Compounds of formula (1); wherein R1 is optionally substituted C1-C3alkyl C2-C3alkenyl, or C2-C3alkynyl, or -NR6R1, -ORB, -SR9 or halogen; R3 is H; optionally substituted C,-Csalkyl, C2-C6alkenyl, C2­C6alkynyl, or C3-C7 cycloalkyl, halogen; OH or OR10; R4 is H, optionally substituted C1­C6alkyl, 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 R7, R8, R9 and R10 are optionally substituted C1-C3alkyl, C2-C3alkenyl, C2-C3alkynyl, or C3-C7 cycloalkyl; are purine receptor, particularly adenosine receptor antagonists, useful for treatment of, inter alia, movement disorders such as Parkinsons disease.

  式（1）的化合物；其中R1是可选择取代的C1-C3烷基，C2-C3烯基，或C2-C3炔基，或-NR6R1，-ORB，-SR9或卤素；R3是H；可选择取代的C1-C6烷基，C2-C6烯基，C2-C6炔基，或C3-C7环烷基，卤素；OH或OR10；R4是H，可选择取代的C1-C6烷基，C3-C6烯基，C3-C6炔基，C3-C7环烷基，芳基或杂环芳基，R5是H或可选择取代的C1-C6烷基，C3-C6烯基，C3-C6炔基，或C3-C7环烷基；或R4和R5共同形成5或6元杂环；而R7，R8，R9和R10是可选择取代的C1-C3烷基，C2-C3烯基，C2-C3炔基，或C3-C7环烷基；是嘌呤受体，特别是腺苷受体拮抗剂，用于治疗包括帕金森病在内的运动障碍。
• Pyrimidine Compounds as Purine Receptor Antagonist
  申请人：Gillespie Roger John

  公开号：US20080182860A1

  公开（公告）日：2008-07-31

  Compounds of formula (1); wherein R 1 is optionally substituted C 1 -C 3 alkyl C 2 -C 3 alkenyl, or C 2 -C 3 alkynyl, or —NR 6 R 1 , —ORB, —SR 9 or halogen; R 3 is II; optionally substituted C,-Csalkyl, C 2 -C 6 alkenyl, C 2 C 6 alkynyl, or C 3 -C 7 cycloalkyl, halogen; OH or OR 10 ; 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 7 , R 8 , R 9 and R 10 are optionally substituted C 1 -C 3 alkyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, or C 3 -C 7 cycloalkyl; are purine receptor, particularly adenosine receptor antagonists, useful for treatment of, inter alia, movement disorders such as Parkinsons disease.

  化合物的式子为（1）; 其中R1为可选择取代的C1-C3烷基，C2-C3烯基或C2-C3炔基，或—NR6R1，—ORB，—SR9或卤素; R3为II; 可选择取代的C,-Cs烷基，C2-C6烯基，C2C6炔基或C3-C7环烷基，卤素; OH或OR10; R4为H，可选择取代的C1C6烷基，C3-C6烯基，C3-C6炔基，C3-C7环烷基，芳基或杂环芳基，R5为H或可选择取代的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; 而R7，R8，R9和R10可选择取代的C1-C3烷基，C2-C3烯基，C2-C3炔基或C3-C7环烷基; 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 ANTAGONISTS
  申请人：VERNALIS (R&D) LTD

  公开号：EP1722798B1

  公开（公告）日：2010-10-20
• PYRIMIDINE COMPOUNDS AS PURINE RECEPTOR ANTAGONIST
  申请人：VERNALIS (R&D) LTD

  公开号：EP1722798A1

  公开（公告）日：2006-11-22
• 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.