2-(5-methyl-2-furyl)-6-(1,3-thiazol-2-yl)pyrimidin-4-ol | 856173-67-6

• 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-(5-methyl-2-furyl)-6-(1,3-thiazol-2-yl)pyrimidin-4-ol
• 英文别名: 2-(5-Methyl-2-furyl)-6-(1,3-thiazol-2-yl)pyrimidin-4-ol；2-(5-methylfuran-2-yl)-4-(1,3-thiazol-2-yl)-1H-pyrimidin-6-one
• CAS: 856173-67-6
• 化学式: C₁₂H₉N₃O₂S
• 分子量: 259.288
• InChiKey: QCRZYBAHTBCZIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：
  95.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(5-methyl-2-furyl)-6-(1,3-thiazol-2-yl)pyrimidin-4-ol 在 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 生成 4-chloro-2-(5-methyl-2-furyl)-6-(1,3-thiazol-2-yl)pyrimidine
  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：

  5-甲基呋喃-2-甲酰亚胺酰胺盐酸盐 、 3-氧代-3-噻唑-2-丙酸乙酯 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 12.0h， 以50%的产率得到2-(5-methyl-2-furyl)-6-(1,3-thiazol-2-yl)pyrimidin-4-ol
  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

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。
• Substituted Pyrimidines as Adenosine Receptor Antagonists
  申请人：Slee Deborah

  公开号：US20080275064A1

  公开（公告）日：2008-11-06

  Compounds of formula (I), including pharmaceutically acceptable salts, esters, solvates and stereoisomers thereof, R 1 , R 2 and R 3 are as defined herein. Pharmaceutical compositions containing a compound of structure (I), as well as methods relating to the use thereof as antagonists of adenosine receptors, in particular antagonists of the A2A adenosine receptor subtype.

  式(I)的化合物，包括药学上可接受的盐、酯、溶剂合物和立体异构体，其中R1、R2和R3的定义如本文所述。含有式(I)化合物的制药组合物，以及与其使用作为腺苷受体拮抗剂相关的方法，特别是A2A腺苷受体亚型的拮抗剂。
• 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.
• WO2007/84914
  申请人：——

  公开号：——

  公开（公告）日：——