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1,3-Diphenyl-6-(4-phenylpiperidin-1-yl)-1,2,4-benzotriazin-7-one | 1416472-98-4

中文名称
——
中文别名
——
英文名称
1,3-Diphenyl-6-(4-phenylpiperidin-1-yl)-1,2,4-benzotriazin-7-one
英文别名
1,3-diphenyl-6-(4-phenylpiperidin-1-yl)-1,2,4-benzotriazin-7-one
1,3-Diphenyl-6-(4-phenylpiperidin-1-yl)-1,2,4-benzotriazin-7-one化学式
CAS
1416472-98-4
化学式
C30H26N4O
mdl
——
分子量
458.563
InChiKey
LGKGPEYEYIUKEC-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    6.1
  • 重原子数:
    35
  • 可旋转键数:
    4
  • 环数:
    6.0
  • sp3杂化的碳原子比例:
    0.17
  • 拓扑面积:
    48.3
  • 氢给体数:
    0
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    4-苯基哌啶1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-one四氢呋喃 为溶剂, 反应 1.0h, 以93%的产率得到1,3-Diphenyl-6-(4-phenylpiperidin-1-yl)-1,2,4-benzotriazin-7-one
    参考文献:
    名称:
    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
    摘要:
    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.
    DOI:
    10.1016/j.ejmech.2012.10.003
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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.
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