(7-imino-3-phenyl-2-thioxo-3,7-dihydro-2H-thiazolo[4,5-d]pyrimidin-6-yl)urea | 1215299-91-4

• 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: (7-imino-3-phenyl-2-thioxo-3,7-dihydro-2H-thiazolo[4,5-d]pyrimidin-6-yl)urea
• 英文别名: (7-imino-3-phenyl-2-thioxo-3,7-dihydro-2H-thiazolo[4,5-d]pyrimidin-6-yl)-urea；(7-Imino-3-phenyl-2-sulfanylidene-[1,3]thiazolo[4,5-d]pyrimidin-6-yl)urea
• CAS: 1215299-91-4
• 化学式: C₁₂H₁₀N₆OS₂
• 分子量: 318.383
• InChiKey: FBSHBBFKBHCSKI-UHFFFAOYSA-N

物化性质

• 熔点：
  225 °C
• 密度：
  1.71±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 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：
  155
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  盐酸氨基脲 、 4-(ethoxymethylene)amino-3-phenlyl-2-thioxo-2,3-dihydro-1,3-thiazole-5-carbonitrile 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以85%的产率得到(7-imino-3-phenyl-2-thioxo-3,7-dihydro-2H-thiazolo[4,5-d]pyrimidin-6-yl)urea
  参考文献：
  名称：

  Synthesis of novel 7-imino-2-thioxo-3,7-dihydro-2H-thiazolo [4,5-d] pyrimidine derivatives as adenosine A2A receptor antagonists

  摘要：

  Novel bicyclic thiazolopyrimidine compounds (15-26) were synthesized to develop adenosine A(2A) receptor (A(2A)R) antagonist for the treatment of Parkinson's disease (PD). The binding affinity of the compounds (15-26) with A(2A)R was evaluated using radioligand binding assay on isolated membranes from stably transfected HEK293 cells. Selectivity of the compounds towards A(2A)R was assessed by comparing their binding affinities with A(1) receptors (A(1)R). cAMP concentrations were measured from HEK293 cells treated with compounds (15-26) as compared to NECA (A(2A)R agonist). The compound (16) possessed strongest A(2A)R binding affinity (K-i value = 0.0038 nM) and selectivity (737-fold) versus A(1)R. Decrease in A(2A)R-coupled release of endogenous cAMP from HEK293 cells treated with compounds (15-26) is evocative of their potential as A(2A)R antagonist. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.133

文献信息

• [EN] A NOVEL 3-SUBSTITUTED 7-IMINO-2-THIOXO-3, 7-DIHYDRO-2H-THIAZOLO [4,5-DI PYRIMIDIN-6-YL - AND PROCESS FOR PREPARATION THEREOF<br/>[FR] (7-IMINO-2-THIOXO-3,7-DIHYDRO-2H-THIAZOLO[4,5-D]PYRIMIDIN-6-YLE SUBSTITUÉ EN POSITION 3 INÉDIT ET SON PROCÉDÉ DE PRÉPARATION
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2011061754A9

  公开（公告）日：2012-07-05
• A NOVEL 3-SUBSTITUTED 7-IMINO-2-THIOXO-3, 7-DIHYDRO-2H-THIAZOLO [4,5-DI PYRIMIDIN-6-YL - AND PROCESS FOR PREPARATION THEREOF
  申请人：Council of Scientific & Industrial Research

  公开号：EP2501706B1

  公开（公告）日：2014-08-06
• NOVEL 3-SUBSTITUTED 7-IMINO-2-THIOXO-3, 7-DIHYDRO-2H-THIAZOLO [4,5-DI PYRIMIDIN-6-YL - AND PROCESS FOR PREPARATION THEREOF
  申请人：Luthra Pratibha Mehta

  公开号：US20120264937A1

  公开（公告）日：2012-10-18

  The present invention relates to novel 3-substituted (7-imino-2-thioxo-3,7-dihydro-2H-thiazolo[4,5-d]pyrimidin-6-yl of formula 1 wherein R is selected from a group consisting of hydrogen, alkyl having carbon no up to 10, allyl, cycloalkyl, aromatic, substituted aromatics (halogen, OH, COOH, OCH 3 , alkyl, etc), pyridyl, piperidine, piprazine, morphine. R 1 is selected from a group consisting of NH 2 , NHR, N(R) 2 (wherein R could be aliphatic or olefinic group up to 10 carbon), hetrocycles such as furan, thiophene, pyrole, prydyl, piprazine, morphine and R 2 is 0 and S separately. Particularly the present invention relates to (7-Imino-3-substituted -2-thioxo-3,7-dihydro-2H-thiazolo[4,5-d]pyrimidin-6-yl)-urea(15-21) and Furan-2-carboxylic acid (7-imino-3 -substituted -2-thioxo-3,7-dihydro-2H-thiazolo[4,5-d]pyrimidin-6-yl)-amide. The compounds of present invention are useful in the treatment of central nervous disorders including, Parkinson disease, Huntington's disease, attention disorder, cognition, Alzheimer disease, depression and hypertension.
• US8835442B2
  申请人：——

  公开号：US8835442B2

  公开（公告）日：2014-09-16
• Synthesis of novel 7-imino-2-thioxo-3,7-dihydro-2H-thiazolo [4,5-d] pyrimidine derivatives as adenosine A2A receptor antagonists
  作者：Pratibha Mehta Luthra、Chandra Bhushan Mishra、Pawan Kumar Jha、Sandeep Kumar Barodia

  DOI：10.1016/j.bmcl.2009.11.133

  日期：2010.2

  Novel bicyclic thiazolopyrimidine compounds (15-26) were synthesized to develop adenosine A(2A) receptor (A(2A)R) antagonist for the treatment of Parkinson's disease (PD). The binding affinity of the compounds (15-26) with A(2A)R was evaluated using radioligand binding assay on isolated membranes from stably transfected HEK293 cells. Selectivity of the compounds towards A(2A)R was assessed by comparing their binding affinities with A(1) receptors (A(1)R). cAMP concentrations were measured from HEK293 cells treated with compounds (15-26) as compared to NECA (A(2A)R agonist). The compound (16) possessed strongest A(2A)R binding affinity (K-i value = 0.0038 nM) and selectivity (737-fold) versus A(1)R. Decrease in A(2A)R-coupled release of endogenous cAMP from HEK293 cells treated with compounds (15-26) is evocative of their potential as A(2A)R antagonist. (C) 2009 Elsevier Ltd. All rights reserved.