2-(2-furyl)-6-(1,3-thiazol-2-yl)pyrimidin-4-amine | 856172-97-9

• 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-(2-furyl)-6-(1,3-thiazol-2-yl)pyrimidin-4-amine
• 英文别名: 2-(2-furyl)-6-(1,3-thiazol-2-yl)pyramidin-4-amine；2-(Furan-2-yl)-6-(1,3-thiazol-2-yl)pyrimidin-4-amine
• CAS: 856172-97-9
• 化学式: C₁₁H₈N₄OS
• 分子量: 244.277
• InChiKey: AUIZMHDUSGWFRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2-furyl)-6-(1,3-thiazol-2-yl)pyrimidin-4-amine 、 氯乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-chloro-N-(2-furan-2-yl-6-thiazol-2-yl-pyramidin-4-yl)-acetamide
  参考文献：
  名称：

  Identification of Novel, Water-Soluble, 2-Amino-N-pyrimidin-4-yl Acetamides as A_2A Receptor Antagonists with In Vivo Efficacy

  摘要：

  Potent adenosine hA(2A) receptor antagonists are often accompanied by poor aqueous solubility, which presents issues for drug development. Herein we describe the early exploration of the structure-activity relationships of a lead pyrimidin-4-yl acetamide series to provide potent and selective 2-amino-N-pyrimidin4-yl acetamides as hA(2A) receptor antagonists with excellent aqueous solubility. In addition, this series of compounds has demonstrated good bioavailability and in vivo efficacy in a rodent model of Parkinson's disease, despite having reduced potency for the rat A(2A) receptor versus the human A2A receptor.

  DOI：

  10.1021/jm070623o
• 作为产物：
  描述：

  4-chloro-2-(2-furyl)-6-(1,3-thiazol-2-yl)pyrimidine 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以53%的产率得到2-(2-furyl)-6-(1,3-thiazol-2-yl)pyrimidin-4-amine
  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。
• Identification of Novel, Water-Soluble, 2-Amino-<i>N</i>-pyrimidin-4-yl Acetamides as A_2A Receptor Antagonists with In Vivo Efficacy
  作者：Deborah H. Slee、Xiaohu Zhang、Manisha Moorjani、Emily Lin、Marion C. Lanier、Yongsheng Chen、Jaimie K. Rueter、Sandra M. Lechner、Stacy Markison、Siobhan Malany、Tanya Joswig、Mark Santos、Raymond S. Gross、John P. Williams、Julio C. Castro-Palomino、María I. Crespo、Maria Prat、Silvia Gual、José-Luis Díaz、Jenny Wen、Zhihong O’Brien、John Saunders

  DOI：10.1021/jm070623o

  日期：2008.2.1

  Potent adenosine hA(2A) receptor antagonists are often accompanied by poor aqueous solubility, which presents issues for drug development. Herein we describe the early exploration of the structure-activity relationships of a lead pyrimidin-4-yl acetamide series to provide potent and selective 2-amino-N-pyrimidin4-yl acetamides as hA(2A) receptor antagonists with excellent aqueous solubility. In addition, this series of compounds has demonstrated good bioavailability and in vivo efficacy in a rodent model of Parkinson's disease, despite having reduced potency for the rat A(2A) receptor versus the human A2A receptor.
• 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