2-chloro-N-[2-(5-methyl-furan-2-yl)-6-thiazol-2-yl-pyrimidin-4-yl]-acetamide | 912940-73-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-chloro-N-[2-(5-methyl-furan-2-yl)-6-thiazol-2-yl-pyrimidin-4-yl]-acetamide
• 英文别名: 2-chloro-N-[2-(5-methylfuran-2-yl)-6-(1,3-thiazol-2-yl)pyrimidin-4-yl]acetamide
• CAS: 912940-73-9
• 化学式: C₁₄H₁₁ClN₄O₂S
• 分子量: 334.786
• InChiKey: VRERKECNUNRLLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2-羟乙基)-吡咯烷 、 2-chloro-N-[2-(5-methyl-furan-2-yl)-6-thiazol-2-yl-pyrimidin-4-yl]-acetamide 在 sodium hydride 、 四丁基碘化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.67h， 生成 N-[2-(5-methyl-furan-2-yl)-6-thiazol-2-yl-pyrimidin-4-yl]-2-(2-pyrrolidin-1-yl-ethoxy)acetamide
  参考文献：
  名称：

  [EN] 2, 6-DI (HETERO) ARYL -4-AMIDO-PYRIMIDINES AS ADENOSINE RECEPTOR ANTAGONISTS
  [FR] PYRIMIDINES SUBSTITUEES UTILISEES COMME ANTAGONISTES DU RECEPTEUR D'ADENOSINE

  摘要：

  公开号：

  WO2006110884A3
• 作为产物：
  描述：

  2-(5-methyl-2-furyl)-6-(1,3-thiazol-2-yl)pyrimidin-4-ylamine 、 氯乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到2-chloro-N-[2-(5-methyl-furan-2-yl)-6-thiazol-2-yl-pyrimidin-4-yl]-acetamide
  参考文献：
  名称：

  WO2007/84914

  摘要：

  公开号：

文献信息

• 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.
• Synthesis of N-pyrimidinyl-2-phenoxyacetamides as adenosine A2A receptor antagonists
  作者：Xiaohu Zhang、Jaimie K. Rueter、Yongsheng Chen、Manisha Moorjani、Marion C. Lanier、Emily Lin、Raymond S. Gross、John E. Tellew、John P. Williams、Sandra M. Lechner、Stacy Markison、Tanya Joswig、Siobhan Malany、Mark Santos、Julio C. Castro-Palomino、Marı´a I. Crespo、Maria Prat、Silvia Gual、José-Luis Díaz、John Saunders、Deborah H. Slee

  DOI：10.1016/j.bmcl.2008.02.032

  日期：2008.3

  A series of N-pyrimidinyl-2-phenoxyacetamide adenosine A(2A) antagonists is described. SAR studies led to compound 14 with excellent potency ( K-i = 0.4 nM), selectivity ( A(1)/A(2A) > 100), and efficacy ( MED 10 mg/ kg po) in the rat haloperidol- induced catalepsy model for Parkinson's disease. (C) 2008 Elsevier Ltd. All rights reserved.
• 2, 6-DI (HETERO) ARYL -4-AMIDO-PYRIMIDINES AS ADENOSINE RECEPTOR ANTAGONISTS
  申请人：Almirall, S.A.

  公开号：EP1888565B1

  公开（公告）日：2011-03-23
• PHENOXY-SUBSTITUTED PYRIMIDINES AS ADENOSINE RECEPTOR ANTAGONISTS
  申请人：NEUROCRINE BIOSCIENCES, INC.

  公开号：EP1976851A2

  公开（公告）日：2008-10-08