1,3-diphenyl-6-(phenylthio)benzo[e][1,2,4]triazin-7(1H)-one | 1312543-75-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,3-diphenyl-6-(phenylthio)benzo[e][1,2,4]triazin-7(1H)-one
• 英文别名: 1,3-diphenyl-6-(phenylsulfanyl)benzo[e][1,2,4]triazin-7(1H)-one；1,3-Diphenyl-6-phenylsulfanyl-1,2,4-benzotriazin-7-one
• CAS: 1312543-75-1
• 化学式: C₂₅H₁₇N₃OS
• 分子量: 407.495
• InChiKey: XSBNYOLTPQTPRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-diphenyl-6-(phenylthio)benzo[e][1,2,4]triazin-7(1H)-one 在 N-碘代丁二酰亚胺 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以84%的产率得到8-Iodo-1,3-diphenyl-6-phenylsulfanyl-1,2,4-benzotriazin-7-one
  参考文献：
  名称：

  银（I）介导的非氧化和氧化的分子内钯催化环化反应合成三氮杂蒽酮

  摘要：

  氟化银（I）介导的1,3-二苯基和8-碘-1,3-二苯基苯并[ e ] [1,2,4]三嗪7（1 ）的分子内非氧化和氧化钯催化的环化反应H）-一6a（R = H）和7a（R = I）提供了一个新的“生物碱样”环系2-苯基-6 H- [1,2,4] triazino [5,6,1- jk ]咔唑-6一8a（三氮杂蒽酮），产率分别为86％和100％。此外，这些环化方案还用于制备三氮杂氟蒽酮类似物8b – e，在C-5处带有二烷基氨基，甲氧基和苯基硫烷基取代基，它们也是由三氮杂氟蒽酮独立合成的8a通过区域选择性亲核加成。类似的AgF介导的8,10-二氢-1-碘-10-苯基吩嗪-2（7 H）-ones的分子内非氧化和氧化钯催化的环化反应13产生了新的“生物碱样”环系统8 H-吲哚[1] ，2,3- MN ]吩嗪-8-酮14分别在80分18％的收率。

  DOI：

  10.1021/jo200966k
• 作为产物：
  描述：

  1,4-dihydro-1,3-diphenylbenzo[e][1,2,4]triazin-4-yl 在 manganese(IV) oxide 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 168.5h， 生成 1,3-diphenyl-6-(phenylthio)benzo[e][1,2,4]triazin-7(1H)-one
  参考文献：
  名称：

  1,3-二苯基苯并[ e ] [1,2,4]三嗪-7（1 H）-one：C-6，C-7和C-8位置处的选定化学物质†

  摘要：

  1,3-二苯基苯并[ e ] [1,2,4]三嗪-7（1 H）-one（6）与四氰基乙烯 （TCNE）或 四氰基环氧乙烷 （TCNEO）给深绿色 2- [1,3-二苯基苯并[ e ] [1,2,4]三嗪-7（1 H）-亚烷基]丙烷腈（11）的产率分别为17％和15％。亲核试剂（例如胺，醇盐，硫醇和格氏试剂）均在C-6处与1,3-二苯基苯并三嗪酮6发生区域选择性反应，而卤化剂仅在C-8处反应。此外，8-碘-1,3-二苯基苯并[ e ] [1,2,4]三嗪-7（1 H）-one（32）经历钯催化的Suzuki-Miyaura和Stille偶联反应，得到8-芳基或杂芳基取代的苯并三嗪酮。通过结合使用C-6和C-8化学1,3,6,8-四苯基苯并[ e ] [1,2,4]三嗪-7（1 H）-one（42）和1,3-二苯基-6,8-二（噻吩-2-基）-苯并[ e ] [1,2,4]三嗪-7（1 H）-

  DOI：

  10.1039/c1ob05410d

文献信息

• Design, synthesis and biological evaluation of benzo[e][1,2,4]triazin-7(1H)-one and [1,2,4]-triazino[5,6,1-jk]carbazol-6-one derivatives as dual inhibitors of beta-amyloid aggregation and acetyl/butyryl cholinesterase
  作者：Marco Catto、Andrey A. Berezin、Daniele Lo Re、Georgia Loizou、Marina Demetriades、Angelo De Stradis、Francesco Campagna、Panayiotis A. Koutentis、Angelo Carotti

  DOI：10.1016/j.ejmech.2012.10.003

  日期：2012.12

  Alzheimer's disease (AD) onset and progression are associated with the dysregulation of multiple and complex physiological processes and a successful therapeutic approach should therefore address more than one target. Two new chemical entities, the easily accessible heterocyclic scaffolds 1,3-diphenylbenzo [e][1,2,4ltriazin-7(1H)-one (benzotriazinone I) and 2-phenyl-6H-[1,2,4]triazino[5,6,1-Acarbazol-6-one (triazafluoranthenone II), were explored for their multitarget-directed inhibition of beta-amyloid (A beta) fibrillization and acetyl- (AChE) and/or butyryl- (BChE) cholinesterase, three valuable targets for AD therapy. Introduction of appropriate amine substituents at positions 6 and 5 on scaffold I and II, respectively, allowed the preparation of a series of compounds that were tested as A beta(1-40) aggregation and cholinesterase inhibitors. Potent inhibitors of A beta self-aggregation were discovered and among them benzotriazinone 7 exhibited an outstanding IC50 equal to 0.37 mu M. Compounds bearing a basic amine linked to the heterocyclic scaffold through a linear alkyl chain of varying length also afforded good ChE inhibitors. In particular, benzotriazinone 24 and triazafluoranthenone 38 were endowed with an interesting multiple activity, the former displaying IC50 values of 1.4, 1.5 and 1.9 mu M on A beta aggregation and AChE and BChE inhibition, respectively, and the latter showing IC50 values of 1.4 and an outstanding 0.025 mu M in the A beta aggregation and BChE inhibition, respectively. Benzotriazinone 24 and triazafluoranthenone 29, selected owing to their suitable aqueous solubility and A beta aggregation inhibition, were submitted to a time course kinetic assay followed with thioflavin T (ThT) spectrofluorimetry, circular dichroism (CD) and transmission electron microscopy (TEM). Experimental data indicated that 24 acted at a low concentration ratio (10 mu M 24 vs. 50 mu M A beta), stabilizing the unstructured A beta peptide and inhibiting fibrillogenesis, and that 29 also acted as fibrillization inhibitor, but likely enhancing and stabilizing the beta-sheet arrangement of A beta to yield protofibrillar species as detected by TEM. (C) 2012 Elsevier Masson SAS. All rights reserved.