7-methyl-6,7-dihydro[1,3]thiazolo[3,2-a][1,2,3]triazolo[4,5-d]pyrimidin-9(1H)-one

• 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: 7-methyl-6,7-dihydro[1,3]thiazolo[3,2-a][1,2,3]triazolo[4,5-d]pyrimidin-9(1H)-one
• 英文别名: 12-Methyl-10-thia-1,4,5,6,8-pentaazatricyclo[7.3.0.0^{3,7}]dodeca-3(7),4,8-trien-2-one；12-methyl-10-thia-1,4,5,6,8-pentazatricyclo[7.3.0.03,7]dodeca-3,6,8-trien-2-one
• 化学式: C₇H₇N₅OS
• 分子量: 209.231
• InChiKey: WBHQTBNEJTXXLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  99.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,2-二溴丙烷 、 5-硫代-2,3-二氢三唑并[4,5-e]嘧啶-7-酮 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以96%的产率得到7-methyl-6,7-dihydro[1,3]thiazolo[3,2-a][1,2,3]triazolo[4,5-d]pyrimidin-9(1H)-one
  参考文献：
  名称：

  2-(Benzimidazol-2-yl)quinoxalines:  A Novel Class of Selective Antagonists at Human A₁ and A₃ Adenosine Receptors Designed by 3D Database Searching

  摘要：

  The Cambridge Structural Database (CSD) was searched through two 3D queries based on substructures shared by well-known antagonists at the A(1) and A(3) adenosine receptors (ARs). Among the resulting 557 hits found in the CSD, we selected five compounds to purchase, synthesize, or translate synthetically into analogues better tailored to interact with the biological targets. Binding experiments using human ARs showed that four out of five tested compounds turned out to be antagonists at the A(1)AR or A(3)AR with K-i values between 50 and 440 nM. Lead optimizations of 2-(benzimidazol-2-yl)quinoxalines (BIQs, 3) gave the best results in terms of potency and selectivity at the A(1) and A(3) ARs. Particularly, 2-(4-etliylthiobenzimidazol-2-yl)quinoxaline (3e) exhibited K-i values at the A(1)AR, A(2A)AR, and A(3)AR, of 0.5, 3440, and 955 nM, respectively, whereas 2-(4-methylbenzimidazol-2-yl)quinoxaline (3b) displayed at the same ARs K-i values of 8000, 833, and 26 nM, respectively.

  DOI：

  10.1021/jm050792d

文献信息

• 2-(Benzimidazol-2-yl)quinoxalines:  A Novel Class of Selective Antagonists at Human A₁ and A₃ Adenosine Receptors Designed by 3D Database Searching
  作者：Ettore Novellino、Barbara Cosimelli、Marina Ehlardo、Giovanni Greco、Manuela Iadanza、Antonio Lavecchia、Maria Grazia Rimoli、Annalisa Sala、Antonio Da Settimo、Giampaolo Primofiore、Federico Da Settimo、Sabrina Taliani、Concettina La Motta、Karl-Norbert Klotz、Daniela Tuscano、Maria Letizia Trincavelli、Claudia Martini

  DOI：10.1021/jm050792d

  日期：2005.12.1

  The Cambridge Structural Database (CSD) was searched through two 3D queries based on substructures shared by well-known antagonists at the A(1) and A(3) adenosine receptors (ARs). Among the resulting 557 hits found in the CSD, we selected five compounds to purchase, synthesize, or translate synthetically into analogues better tailored to interact with the biological targets. Binding experiments using human ARs showed that four out of five tested compounds turned out to be antagonists at the A(1)AR or A(3)AR with K-i values between 50 and 440 nM. Lead optimizations of 2-(benzimidazol-2-yl)quinoxalines (BIQs, 3) gave the best results in terms of potency and selectivity at the A(1) and A(3) ARs. Particularly, 2-(4-etliylthiobenzimidazol-2-yl)quinoxaline (3e) exhibited K-i values at the A(1)AR, A(2A)AR, and A(3)AR, of 0.5, 3440, and 955 nM, respectively, whereas 2-(4-methylbenzimidazol-2-yl)quinoxaline (3b) displayed at the same ARs K-i values of 8000, 833, and 26 nM, respectively.