2-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-amino-3-phenyl-[1,2,4]triazino[3,2-a]isoquinolin-5-ium ethanesulfonate
• 英文别名: 2-amino-3-phenyl[1,2,4]triazino[3,2-a]isoquinolinium ethanesulfonate；2-amino-3-phenyl-as-triazino[3,2-a]isoquinolinium ethanesulfonate；Ethanesulfonate;3-phenyl-[1,2,4]triazino[3,2-a]isoquinolin-5-ium-2-amine
• 化学式: C₂H₅O₃S*C₁₇H₁₃N₄
• 分子量: 382.443
• InChiKey: BCCHSLSROXQFLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-imino-3-phenyl-2,5-dihydro-as-triazino[3,2-a]isoquinoline 以87%的产率得到2-amino-3-phenyl-[1,2,4]triazino[3,2-a]isoquinolin-5-ium ethanesulfonate
  参考文献：
  名称：

  Condensed quinolinium and isoquinolinium derivatives

  摘要：

  一般式I的新化合物(其中R.sub.1代表C.sub.1-4烷基或芳基烷基；R.sub.2代表羟基；或者R.sub.1和R.sub.2共同形成一个价键；R.sub.3是氢、C.sub.1-4烷基、C.sub.1-4烷氧基、苯基、氨基、烷硫基或者式--NR.sub.7 R.sub.8的基团，在其中R.sub.7和R.sub.8可以相同也可以不同，代表氢、C.sub.1-4烷基、苯基-C.sub.1-4烷基、羟基-C.sub.1-4烷基或者二-(C.sub.1-4烷基)-氨基-C.sub.1-4烷基，或者与氮原子结合形成一个可能含有进一步氮、氧或硫原子的6元杂环环的环；或者R.sub.2和R.sub.3共同形成一个氧代(.dbd.O)或硫代(.dbd.S)基团；R.sub.4代表氢、C.sub.1-4烷基或苯基，可能带有一个或两个卤素或硝基取代基；Z是式(a)或(b)的基团##STR2## A.sup.-代表一个阴离子)及其异构体具有有用的局部麻醉、抗抑郁、镇静安定和平滑肌松弛性质，并伴随着较弱的镇痛作用，在治疗中具有用途。

  公开号：

  US04994448A1

文献信息

• Ellipticine analogues and related compounds as inhibitors of reverse transcriptase and as inhibitors of the efflux pump
  作者：Derek Sharples、György Hajós、Zsuzsanna Riedl、Dorottya Csányi、József Molnár、Diana Szabó

  DOI：10.1002/1521-4184(200109)334:8/9<269::aid-ardp269>3.0.co;2-#

  日期：2001.9

  intercalating, reverse transcriptase (RT) inhibitory and multidrug resistance efflux pump inhibitory properties. The intercalating activity and the RT inhibitory activity of the derivatives suggest that ellipticine analogues bind at an allosteric binding site on RT or that this inhibition could be controlled at the DNA level. The MDR efflux pump inhibitory activities of these derivatives, however, appears to be

  已经合成了十个与玫瑰树碱相关的多环衍生物，并对其嵌入，逆转录酶（RT）抑制和多药耐药性外排泵抑制特性进行了测试。衍生物的嵌入活性和RT抑制活性表明玫瑰树碱类似物在RT的变构结合位点结合，或者这种抑制作用可在DNA水平控制。然而，这些衍生物的MDR外排泵抑制活性似乎与DNA结合能力无关。
• Interaction of novel condensed triazine derivatives with central and peripheral type benzodiazepine receptors: synthesis, in vitro pharmacology and modelling
  作者：Éva Szárics、Zsuzsanna Riedl、Lajos Nyikos、György Hajós、Julianna Kardos

  DOI：10.1016/j.ejmech.2005.10.015

  日期：2006.4

  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.
• US4994448A
  申请人：——

  公开号：US4994448A

  公开（公告）日：1991-02-19