7-chloro-3-(2-furyl)-10-phenyl[1,2,4]triazino[4,3-a]benzimidazol-4(10H)-one | 1359721-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 7-chloro-3-(2-furyl)-10-phenyl[1,2,4]triazino[4,3-a]benzimidazol-4(10H)-one
• 英文别名: 7-Chloro-3-(furan-2-yl)-10-phenyl-[1,2,4]triazino[4,3-a]benzimidazol-4-one
• CAS: 1359721-92-8
• 化学式: C₁₉H₁₁ClN₄O₂
• 分子量: 362.775
• InChiKey: OEWNQGXQPWIWBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 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：
  61.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-4-氯二苯胺 在 苯膦酰二氯 、 一水合肼 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 52.0h， 生成 7-chloro-3-(2-furyl)-10-phenyl[1,2,4]triazino[4,3-a]benzimidazol-4(10H)-one
  参考文献：
  名称：

  3-Aryl-[1,2,4]triazino[4,3-a]benzimidazol-4(10H)-one: A Novel Template for the Design of Highly Selective A_2B Adenosine Receptor Antagonists

  摘要：

  In an effort to identify novel ligands possessing high affinity and selectivity for the A(2B) AR subtype, we further investigated the class of 3-aryl[1,2,4]triazino[4,3-a]benzimidazol-4(10H)-ones V, previously disclosed by us as selective A(1) AR antagonists. Preliminary assays on a number of triazinobenzimidazoles derived from our "in-house" collection revealed that all the derivatives selected showed significant affinity at A(2B) AR, no affinity at A(3) AR, and various degrees of selectivity toward A(1) and A(2A) ARs. Investigation of a new series featuring modified substituents at the 10-position (4'-chlorophenyl or phenylethyl groups), and a chlorine atom at the 7-position (X) of the triazinobenzimidazole nucleus, yielded highly potent and selective A(2B) AR antagonists. The presence of a pendant 3-phenyl ring appears to hamper the interaction with A(2A) AR, conferring high A(2B)/A(2A) AR selectivity. Derivative 13 (X = Cl, R = C6H5) is the most potent and selective compound, with an IC50 of 3.10 nM at A(2B) AR and no affinity at A(1), A(2A), and A(3) ARs.

  DOI：

  10.1021/jm201177b

文献信息

• 3-Aryl-[1,2,4]triazino[4,3-<i>a</i>]benzimidazol-4(10<i>H</i>)-one: A Novel Template for the Design of Highly Selective A_2B Adenosine Receptor Antagonists
  作者：Sabrina Taliani、Isabella Pugliesi、Elisabetta Barresi、Francesca Simorini、Silvia Salerno、Concettina La Motta、Anna Maria Marini、Barbara Cosimelli、Sandro Cosconati、Salvatore Di Maro、Luciana Marinelli、Simona Daniele、Maria Letizia Trincavelli、Giovanni Greco、Ettore Novellino、Claudia Martini、Federico Da Settimo

  DOI：10.1021/jm201177b

  日期：2012.2.23

  In an effort to identify novel ligands possessing high affinity and selectivity for the A(2B) AR subtype, we further investigated the class of 3-aryl[1,2,4]triazino[4,3-a]benzimidazol-4(10H)-ones V, previously disclosed by us as selective A(1) AR antagonists. Preliminary assays on a number of triazinobenzimidazoles derived from our "in-house" collection revealed that all the derivatives selected showed significant affinity at A(2B) AR, no affinity at A(3) AR, and various degrees of selectivity toward A(1) and A(2A) ARs. Investigation of a new series featuring modified substituents at the 10-position (4'-chlorophenyl or phenylethyl groups), and a chlorine atom at the 7-position (X) of the triazinobenzimidazole nucleus, yielded highly potent and selective A(2B) AR antagonists. The presence of a pendant 3-phenyl ring appears to hamper the interaction with A(2A) AR, conferring high A(2B)/A(2A) AR selectivity. Derivative 13 (X = Cl, R = C6H5) is the most potent and selective compound, with an IC50 of 3.10 nM at A(2B) AR and no affinity at A(1), A(2A), and A(3) ARs.