4-(Furan-2-yl)-10-(4-iodophenyl)-12-thia-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7-tetraene-11-thione | 1225514-05-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 4-(Furan-2-yl)-10-(4-iodophenyl)-12-thia-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7-tetraene-11-thione
• CAS: 1225514-05-5
• 化学式: C₁₆H₈IN₅OS₂
• 分子量: 477.309
• InChiKey: QJCMFRSKBIEYMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-呋喃甲酰肼 、 4-(ethoxymethylene)amino-3-(p-iodophenlyl)-2-thioxo-2,3-dihydro-1,3-thiazole-5-carbonitrile 在 异丁酸 作用下， 以 甲苯 为溶剂， 以63%的产率得到4-(Furan-2-yl)-10-(4-iodophenyl)-12-thia-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7-tetraene-11-thione
  参考文献：
  名称：

  Novel 8-(furan-2-yl)-3-substituted thiazolo [5,4-e][1,2,4] triazolo[1,5-c] pyrimidine-2(3H)-thione derivatives as potential adenosine A2A receptor antagonists

  摘要：

  Novel thiazolotriazolopyrimidine derivatives (23-33) designed as potential adenosine A(2A) receptor (A(2A)R) antagonists were synthesized. Molecular docking studies revealed that all compounds (23-33) exhibited strong interaction with A(2A)R. The strong interaction of the compounds (23-33) with A(2A)R in silico was confirmed by their high binding affinity with human A(2A)R stably expressed in HEK293 cells using radioligand-binding assay. The compounds 24-26 demonstrated substantial binding affinity and selectivity for A(2A)R as compared to SCH58261, a standard A(2A)R antagonist. Decrease in A(2A)R-coupled release of endogenous cAMP in treated HEK293 cells demonstrated in vitro A(2A)R antagonist potential of the compounds 24-26. Attenuation in haloperidol-induced motor impairments (catalepsy and akinesia) in Swiss albino male mice pre-treated with compounds 24-26 further supports their role in the alleviation of PD symptoms. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.048

文献信息

• Novel 8-(furan-2-yl)-3-substituted thiazolo [5,4-e][1,2,4] triazolo[1,5-c] pyrimidine-2(3H)-thione derivatives as potential adenosine A2A receptor antagonists
  作者：Chandra Bhushan Mishra、Sandeep Kumar Barodia、Amresh Prakash、J.B. Senthil Kumar、Pratibha Mehta Luthra

  DOI：10.1016/j.bmc.2010.02.048

  日期：2010.4

  Novel thiazolotriazolopyrimidine derivatives (23-33) designed as potential adenosine A(2A) receptor (A(2A)R) antagonists were synthesized. Molecular docking studies revealed that all compounds (23-33) exhibited strong interaction with A(2A)R. The strong interaction of the compounds (23-33) with A(2A)R in silico was confirmed by their high binding affinity with human A(2A)R stably expressed in HEK293 cells using radioligand-binding assay. The compounds 24-26 demonstrated substantial binding affinity and selectivity for A(2A)R as compared to SCH58261, a standard A(2A)R antagonist. Decrease in A(2A)R-coupled release of endogenous cAMP in treated HEK293 cells demonstrated in vitro A(2A)R antagonist potential of the compounds 24-26. Attenuation in haloperidol-induced motor impairments (catalepsy and akinesia) in Swiss albino male mice pre-treated with compounds 24-26 further supports their role in the alleviation of PD symptoms. (C) 2010 Elsevier Ltd. All rights reserved.