2-(5-methyl-2-furyl)-6-(1H-pyrazol-1-yl)pyrimidin-4-ylamine | 856171-70-5

• 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-(5-methyl-2-furyl)-6-(1H-pyrazol-1-yl)pyrimidin-4-ylamine
• 英文别名: 2-(5-methyl-2-furyl)-6-(1H-pyrazol-1-yl)pyrimidin-4-amine；2-(5-Methylfuran-2-yl)-6-pyrazol-1-ylpyrimidin-4-amine
• CAS: 856171-70-5
• 化学式: C₁₂H₁₁N₅O
• 分子量: 241.252
• InChiKey: DJECROXLUBKSKW-UHFFFAOYSA-N

物化性质

• 沸点：
  355.4±42.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  82.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对甲氧基苯乙酸 、 2-(5-methyl-2-furyl)-6-(1H-pyrazol-1-yl)pyrimidin-4-ylamine 在 吡啶 、 草酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(4-methoxyphenyl)-N-[2-(5-methylfuran-2-yl)-6-pyrazol-1-ylpyrimidin-4-yl]acetamide
  参考文献：
  名称：

  2,6-Diaryl-4-phenacylaminopyrimidines as potent and selective adenosine A2A antagonists with reduced hERG liability

  摘要：

  In this report, the design and synthesis of a series of pyrimidine based adenosine A(2A) antagonists are described. The strategy and outcome of expanding SAR exploration to attenuate hERG and improve selectivity over A(1) are discussed. Compound 33 exhibited excellent potency, selectivity over A1, and reduced hERG liability. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.036
• 作为产物：
  描述：

  吡唑 、 6-chloro-2-(5-methylfuran-2-yl)pyrimidin-4-ylamine 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(5-methyl-2-furyl)-6-(1H-pyrazol-1-yl)pyrimidin-4-ylamine
  参考文献：
  名称：

  2-Amino-N-pyrimidin-4-ylacetamides as A_2A Receptor Antagonists: 1. Structure−Activity Relationships and Optimization of Heterocyclic Substituents

  摘要：

  Previously we have described a novel series of potent and selective A(2A) receptor antagonists (e.g., 1) with excellent aqueous solubility.(1) While these compounds are efficacious A(2A) antagonists in vivo, the presence of an unsubstituted furyl moiety was a cause of some concern. In order to avoid the potential metabolic liabilities that could arise from an unsubstituted fury] moiety, an optimization effort was undertaken with the aim of replacing the unsubstituted furan with a more metabolically stable group while maintaining potency and selectivity. Herein, we describe the synthesis and SAR of a range of novel heterocyclic systems and the successful identification of a replacement for the unsubstituted furan moiety with a methylfuran or thiazole moiety while maintaining potency and selectivity.

  DOI：

  10.1021/jm701185v

文献信息

• [EN] 2, 6 BISHETEROARYL-4-AMINOPYRIMIDINES AS ADENOSINE RECEPTOR ANTAGONISTS<br/>[FR] 2, 6-BISHETEROARYL-4-AMINOPYRIMIDINES UTILISEES EN TANT QU'ANTAGONISTES DES RECEPTEURS DE L'ADENOSINE
  申请人：ALMIRALL PRODESFARMA SA

  公开号：WO2005058883A1

  公开（公告）日：2005-06-30

  4-Aminopyrimidine derivatives of formula (I) FORMULA heteroaryl groups, including pharmaceutically acceptable salts thereof, wherein R1 and R2 are adenosine A2A receptor antagonists useful in the treatment of movement disorders such as Parkinson's disease.

  公式（I）的4-氨基嘧啶衍生物，包括其药学上可接受的盐，其中R1和R2是阿多诺苷A2A受体拮抗剂，可用于治疗帕金森病等运动障碍。
• 2,6 Bisheteroaryl-4-Aminopyrimidines as Adenosine Receptor Antagonists
  申请人：Crespo Crespo Maria Isabel

  公开号：US20080058356A1

  公开（公告）日：2008-03-06

  4-Aminopyrimidine derivatives of formula (I) FORMULA heteroaryl groups, including pharmaceutically acceptable salts thereof, wherein R 1 and R 2 are adenosine A 2A receptor antagonists useful in the treatment of movement disorders such as Parkinson's disease.

  公式（I）的4-氨基嘧啶衍生物，其中包括杂环基团，以及其药学上可接受的盐，其中R1和R2是阿多诺西嗪A2受体拮抗剂，适用于治疗运动障碍，如帕金森病。
• 2-Amino-<i>N</i>-pyrimidin-4-ylacetamides as A_2A Receptor Antagonists: 1. Structure−Activity Relationships and Optimization of Heterocyclic Substituents
  作者：Deborah H. Slee、Yongsheng Chen、Xiaohu Zhang、Manisha Moorjani、Marion C. Lanier、Emily Lin、Jaimie K. Rueter、John P. Williams、Sandra M. Lechner、Stacy Markison、Siobhan Malany、Mark Santos、Raymond S. Gross、Kayvon Jalali、Yang Sai、Zhiyang Zuo、Chun Yang、Julio C. Castro-Palomino、María I. Crespo、Maria Prat、Silvia Gual、José-Luis Díaz、John Saunders

  DOI：10.1021/jm701185v

  日期：2008.3.1

  Previously we have described a novel series of potent and selective A(2A) receptor antagonists (e.g., 1) with excellent aqueous solubility.(1) While these compounds are efficacious A(2A) antagonists in vivo, the presence of an unsubstituted furyl moiety was a cause of some concern. In order to avoid the potential metabolic liabilities that could arise from an unsubstituted fury] moiety, an optimization effort was undertaken with the aim of replacing the unsubstituted furan with a more metabolically stable group while maintaining potency and selectivity. Herein, we describe the synthesis and SAR of a range of novel heterocyclic systems and the successful identification of a replacement for the unsubstituted furan moiety with a methylfuran or thiazole moiety while maintaining potency and selectivity.
• 2,6-BISHETEROARYL-4-AMINOPYRIMIDINES AS ADENOSINE RECEPTOR ANTAGONISTS
  申请人：Almirall Prodesfarma AG

  公开号：EP1697351A1

  公开（公告）日：2006-09-06
• JP2007514003A
  申请人：——

  公开号：JP2007514003A

  公开（公告）日：2007-05-31