2-phenyl-6H-[1,2,4]triazino-[5,6,1-jk]carbazol-6-one | 1312543-84-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-phenyl-6H-[1,2,4]triazino-[5,6,1-jk]carbazol-6-one
• 英文别名: 3-Phenyl-1,2,4-triazatetracyclo[7.6.1.05,16.010,15]hexadeca-2,4,6,9(16),10,12,14-heptaen-8-one
• CAS: 1312543-84-2
• 化学式: C₁₉H₁₁N₃O
• 分子量: 297.316
• InChiKey: MANXJZVZCMYUIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenyl-6H-[1,2,4]triazino-[5,6,1-jk]carbazol-6-one 在 1,3,5,7,2,4,6,8-四硫杂四氮杂环辛四烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以79%的产率得到2-phenyl-7H-[1,2,5]thiadiazolo[3,4-b][1,2,4]triazino[1,6,5-lm]carbazol-7-one
  参考文献：
  名称：

  氧化还原活性喹啉1,2,4-苯并三嗪

  摘要：

  通过将N1-苯基替换为N1-苯基，修饰对-喹啉亚胺1,3-二苯基-1,2,4-苯并三嗪-7（1 H）-一（2a）（E 1/2 –1/0 -1.20 V）通过循环伏安法和计算研究确定，五氟苯基，三氟甲基的C3-苯基或亚甲基丙二腈的C7羰基可改善电子亲和力。结合结构变化进一步提高了电子接受能力：最缺乏电子的类似物（E 1/2 –1/0约-0.65V）涉及将C7处的亚甲基丙二腈基团与C3处的三氟甲基基团结合。在C5–C6处的1,2,5-噻二唑融合不会影响氧化还原行为，但会增强UV-vis吸收特性。在噻二唑类似物的合成过程中，以低产率获得了1，4-噻嗪基融合的类似物6，其热环收缩至三氮杂蒽酮7。对化合物进行了充分表征，并提供了所选类似物的X射线数据。

  DOI：

  10.1021/acs.joc.8b01311
• 作为产物：
  描述：

  8-iodo-1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-one 在 bis-triphenylphosphine-palladium(II) chloride 、 silver fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以99%的产率得到2-phenyl-6H-[1,2,4]triazino-[5,6,1-jk]carbazol-6-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

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.
• Redox Active Quinoidal 1,2,4-Benzotriazines
  作者：Georgia A. Zissimou、Andreas Kourtellaris、Maria Manoli、Panayiotis A. Koutentis

  DOI：10.1021/acs.joc.8b01311

  日期：2018.8.17

  ylidenemalononitrile groups at C7 with the trifluoromethyl groups at C3. 1,2,5-Thiadiazolo fusion at C5–C6 did not affect the redox behavior but did enhance the UV–vis absorption profile. During the synthesis of the thiadiazolo analogues, 1,4-thiazino-fused analogues 6 were obtained in low yield, which thermally ring contract to the triazafluoranthenones 7. Compounds are fully characterized, and X-ray

  通过将N1-苯基替换为N1-苯基，修饰对-喹啉亚胺1,3-二苯基-1,2,4-苯并三嗪-7（1 H）-一（2a）（E 1/2 –1/0 -1.20 V）通过循环伏安法和计算研究确定，五氟苯基，三氟甲基的C3-苯基或亚甲基丙二腈的C7羰基可改善电子亲和力。结合结构变化进一步提高了电子接受能力：最缺乏电子的类似物（E 1/2 –1/0约-0.65V）涉及将C7处的亚甲基丙二腈基团与C3处的三氟甲基基团结合。在C5–C6处的1,2,5-噻二唑融合不会影响氧化还原行为，但会增强UV-vis吸收特性。在噻二唑类似物的合成过程中，以低产率获得了1，4-噻嗪基融合的类似物6，其热环收缩至三氮杂蒽酮7。对化合物进行了充分表征，并提供了所选类似物的X射线数据。
• Synthesis of Triazafluoranthenones via Silver(I)-Mediated Nonoxidative and Oxidative Intramolecular Palladium-Catalyzed Cyclizations
  作者：Panayiotis A. Koutentis、Georgia Loizou、Daniele Lo Re

  DOI：10.1021/jo200966k

  日期：2011.7.15

  (AgF)-mediated intramolecular nonoxidative and oxidative palladium-catalyzed cyclizations of 1,3-diphenyl- and 8-iodo-1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-ones 6a (R = H) and 7a (R = I) afford a new ‘alkaloid like’ ring system 2-phenyl-6H-[1,2,4]triazino[5,6,1-jk]carbazol-6-one 8a (triazafluoranthenone) in 86 and 100% yields, respectively. Furthermore, these cyclization protocols were used to prepare triazafluoranthenone

  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。