2-methoxy-3-phenyl-[1,2,4]triazino[3,2-a]isoquinolinium perchlorate

• 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-methoxy-3-phenyl-[1,2,4]triazino[3,2-a]isoquinolinium perchlorate
• 英文别名: 2-methoxy-3-phenyl[1,2,4]triazino[3,2-a]isoquinolinium perchlorate；2-methoxy-3-phenyl-as-triazino[3,2-a]isoquinolinium perchlorate；2-Methoxy-3-phenyl-[1,2,4]triazino[3,2-a]isoquinolin-5-ium;perchlorate
• 化学式: C₁₈H₁₄N₃O*ClO₄
• 分子量: 387.779
• InChiKey: UOIHHKLRXZWRGH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.71
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-methoxy-3-phenyl-[1,2,4]triazino[3,2-a]isoquinolinium perchlorate 在 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 以70%的产率得到2-imino-3-phenyl-2,5-dihydro-as-triazino[3,2-a]isoquinoline
  参考文献：
  名称：

  玫瑰树碱类似物和相关化合物作为逆转录酶抑制剂和外排泵抑制剂。

  摘要：

  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。

  DOI：

  10.1002/1521-4184(200109)334:8/9<269::aid-ardp269>3.0.co;2-#
• 作为产物：
  描述：

  2-amino-1-iminoisoquinoline 在 高氯酸 作用下， 以 乙腈 为溶剂， 反应 9.0h， 生成 2-methoxy-3-phenyl-[1,2,4]triazino[3,2-a]isoquinolinium perchlorate
  参考文献：
  名称：

  Hajos, Gy.; Riedl, Zsuzsanna; Messmer, A., ACH - Models in Chemistry, 1994, vol. 131, # 3-4, p. 397 - 414

  摘要：

  DOI：

文献信息

• Condensed quinolinium and isoquinolinium derivatives
  申请人：Egis Gyogyszergyar

  公开号：US04994448A1

  公开（公告）日：1991-02-19

  The new compounds of the general Formula I ##STR1## (wherein R.sub.1 stands for C.sub.1-4 alkyl or aralkyl; and R.sub.2 represents hydroxy; or R.sub.1 and R.sub.2 together form a valency bond; R.sub.3 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl, amino, alkylthio or a group of the Formula --NR.sub.7 R.sub.8 in which R.sub.7 and R.sub.8 may be the same or different and stand for hydrogen, C.sub.1-4 alkyl, phenyl-C.sub.1-4 alkyl, hydroxy-C.sub.1-4 alkyl or di-(C.sub.1-4 alkyl)-amino-C.sub.1-4 alkyl or together with the nitrogen atom they are attached to form a 6-membered heterocyclic ring which may optionally contain a further nitrogen, oxygen or sulfur atom; or R.sub.2 and R.sub.3 together form an oxo (.dbd.O) or thixo (.dbd.S) group; R.sub.4 represents hydrogen, C.sub.1-4 alkyl or phenyl which may optionally bear one or two halogen or nitro substituent(s); Z is a group of the Formula (a) or (b) ##STR2## A.sup.- represents an anion) and isomers thereof possess useful local anaesthetic, antidepressant, tranquillo-sedative and smooth muscle relaxant properties accompanied by a weaker analgesic effect and are useful in therapy.

  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。
• 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