2-{[3-(dimethylamino)propyl]amino}-3-phenyl-[1,2,4]triazino[3,2-a]isoquinolin-5-ium ethanesulfonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-{[3-(dimethylamino)propyl]amino}-3-phenyl-[1,2,4]triazino[3,2-a]isoquinolin-5-ium ethanesulfonate
• 英文别名: 2-(3-Dimethylaminopropylamino)-3-phenyl-as-triazino[3,2-a]isoquinolinium ethanesulfonate；N',N'-dimethyl-N-(3-phenyl-[1,2,4]triazino[3,2-a]isoquinolin-5-ium-2-yl)propane-1,3-diamine;ethanesulfonate
• 化学式: C₂H₅O₃S*C₂₂H₂₄N₅
• 分子量: 467.592
• InChiKey: RWICCGUGBCMNGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  乙基磺酸 、 N,N-二甲基-1,3-二氨基丙烷 、 2-methoxy-3-phenyl-[1,2,4]triazino[3,2-a]isoquinolinium perchlorate 以 乙腈 为溶剂， 反应 2.0h， 以55%的产率得到2-{[3-(dimethylamino)propyl]amino}-3-phenyl-[1,2,4]triazino[3,2-a]isoquinolin-5-ium ethanesulfonate
  参考文献：
  名称：

  Interaction of novel condensed triazine derivatives with central and peripheral type benzodiazepine receptors: synthesis, in vitro pharmacology and modelling

  摘要：

  Structurally related sets of triazino-quinoline, triazino-isoquinoline and pyrido-triazine derivatives were synthesised and their binding interactions with central (CBR)- and peripheral-type (PBR) benzodiazepine binding sites have been characterised. Of 33 compounds tested, a new compound, 2-(4-methylphenyl)-3H-[1,2,4] triazino [2, 3-a] quinolin-3-one (1 g) showed the lowest CBR binding inhibition constant (K-i = 42 +/- 9 nM) and the highest CBR over PBR selectivity (> 1300). All but the 4-methylphenyl (1 g) structural modifications decreased the affinity and selectivity of the parent compound, 2-phenyl-3H- [ 1,2,4]triazino[2,3-a]quinolin-3-one (1d) (K-i = 69 +/- 9 nM, selectivity > 890). Molecular interactions between selected ligands (standards and triazine derivatives) and alpha(1)gamma(2) subunit-interface residues in a GABA(A) receptor extracellular domain homology model have been calculated. Comparing data with calculations confirmed hydrogen bonding to gamma(2)Thr142 and hydrophobic interaction with alpha 1His101 as being essential for high-affinity CBR binding. (c) 2006 Elsevier SAS. All fights reserved.

  DOI：

  10.1016/j.ejmech.2005.10.015

文献信息

• US4994448A
  申请人：——

  公开号：US4994448A

  公开（公告）日：1991-02-19