91532-29-5Relevant academic research and scientific papers
One-pot synthesis ofN-substituted benzannulated triazolesviastable arene diazonium salts
Faggyas, Réka J.,McGrory, Rochelle,Sutherland, Andrew
, p. 6127 - 6140 (2021/07/21)
A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamidesviastable diazonium salts, prepared using a polymer-supported nitrite reagent andp-tosic acid. The transformation was compatible with a wide range of aryl functional groups and amide/sulfonamide-substituents and was used for the synthesis of pharmaceutically important targets. The synthetic utility of the one-pot diazotisaton-cyclisation process was further demonstrated with the preparation of an α-amino acid containing 1,2,3-benzotriazin-4(3H)-one.
Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one containing 4,5-dihydrothiazole-2-thiol derivatives against Meloidogyne incognita
Chen, Xiulei,Zhou, Zhen,Li, Zhong,Xu, Xiaoyong
, p. 194 - 200 (2019/09/13)
A series of novel 1,2,3-benzotriazin-4-one derivatives containing 4,5-dihydrothiazole-2-thiol were synthesized and characterized by 1H NMR, 13C NMR, 19F NMR and HRMS. The bioassay results showed that compounds 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-7-methoxybenzo[d][1–3]triazin-4(3H)-one, 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-6-nitrobenzo[d][1–3]triazin-4(3H)-one, 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita at the concentration of 10.0 mg L?1 in vivo. Compound 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one showed excellent nematicidal activity with inhibition 68.3% at a concentration of 1.0 mg L?1. It suggested that the structure of 1,2,3-benzotriazin-4-one containing 4,5-dihydro-thiazole-2-thiol could be optimized further.
Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one derivatives containing benzo[d][1,2,3]thiadiazole against Meloidogyne incognita
Chen, Xiulei,Guo, Wei,Li, Zhong,Wang, Gaolei,Xu, Xiaoyong,Zhang, Ruifeng
supporting information, (2020/07/10)
Based on the characteristic of benzo[d][1,2,3]thiadiazole to induce the systemic acquired resistance and improve the immunity of plants, benzo[d][1,2,3]thiadiazole was introduced into 1,2,3-benzotriazin-4-one, thirty-one novel 1,2,3-benzotriazin-4-one derivatives containing benzo[d][1,2,3]thiadiazole were designed and synthesized. Nematicidal activity showed that most of the synthesized compounds exhibited great inhibitory activity in vivo against Meloidogyne incognita at 20 mg/L. Among 31 tested compounds, A2 and A3 showed an excellent nematicidal activity with the inhibition rate of 50.4percent and 53.1percent at the concentration of 1.0 mg/L, respectively. The influence of substituent type and position was investigated. The relationship between structure and activity was also preliminary analyzed.
Synthesis and nematicidal evaluation of 1,2,3-benzotriazin-4-one derivatives containing piperazine as linker against Meloidogyne incognita
Chen, Xiulei,Jia, Haowu,Li, Zhong,Xu, Xiaoyong
supporting information, p. 1207 - 1213 (2019/03/29)
To explore new skeleton with nematicidal activity, a series of novel 1,2,3-benzotriazin-4-one derivatives containing piperazine as linker were synthesized and varied fragments were also introduced to increase structure diversity of the new skeleton. Their inhibitory activities in vivo were evaluated against Meloidogyne incognita. The newly prepared compounds A6, A8, A21, A28 and A38 exhibited more than 50% inhibition at the concentration of 20 mg/L. Especially compound A6 displayed 71.4% inhibition against Meloidogyne incognita at the concentration of 20 mg/L. The nematicidal activities varied significantly depending on the types and positions of the substituents, which provided guidance for further structure modification.
Oxidative Rearrangement of 3-Aminoindazoles for the Construction of 1,2,3-Benzotriazine-4(3 H)-ones at Ambient Temperature
Zhou, Yao,Wang, Ya,Lou, Yixian,Song, Qiuling
supporting information, p. 6494 - 6497 (2018/10/20)
A novel oxidative rearrangement of 3-aminoindazoles is reported, enabling the production of diverse functionalized 1,2,3-benzotriazine-4(3H)-ones in good yields at room temperature. The key success of this unprecedented transformation of 3-aminoindazoles is the use of water as cosolvent, which could facilitate the halogen-induced ring expansion of 3-aminoindazoles under oxidative conditions.
Synthesis and biological evaluation of novel 1,2,3-benzotriazin-4-one derivatives as leukotriene A4 hydrolase aminopeptidase inhibitors
Zhang, Fan,Wu, Dang,Wang, Gao-Lei,Hou, Shuang,Ou-Yang, Ping,Huang, Jin,Xu, Xiao-Yong
supporting information, p. 1044 - 1048 (2017/05/22)
A series of novel 1,2,3-benzotriazin-4-one derivatives were designed, synthesized and their inhibitory activities against leukotriene A4 hydrolase aminopeptidase in vitro were evaluated. Many compounds showed moderate to good activities at the concentration of 10?μmol/L. Among them, compound IV-16 exhibited the highest inhibitory activity up to 80.6% with an IC50 of 1.30?±?0.20?μmol/L. The compound IV-16 was also tested the proliferation inhibitory activities in THP1 human AML cell line and its binding model with LTA4H enzyme by molecular docking was studied. It indicated that 1,2,3-benzotriazin-4-one was a promising scaffold for further study. The relationship between structure and inhibitory activity was also preliminarily discussed.
Synthesis and Nematicidal Activities of 1,2,3-Benzotriazin-4-one Derivatives against Meloidogyne incognita
Wang, Gaolei,Chen, Xiulei,Deng, Yayun,Li, Zhong,Xu, Xiaoyong
, p. 6883 - 6889 (2015/08/18)
A series of novel 1,2,3-benzotriazin-4-one derivatives were synthesized by the reaction of 3-bromoalkyl-1,2,3-benzotriazin-4-ones with potassium salt of 2-cyanoimino-4-oxothiazolidine in the presence of potassium iodide. Nematicidal assays in vivo showed that some of them exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita, up to 100% at the concentration of 10.0 mg L-1, which indicated that 1,2,3-benzotriazin-4-one derivatives might be potential for novel promising nematicides. The nematicidal activity was influenced by the combination of substituent type, substituted position, and linker length in the molecule. The inhibition rate data at the concentrations of 5.0 and 1.0 mg L-1 for the compounds with high inhibitory activities were also provided. When tested in vitro, none of them showed direct inhibition against M. incognita. The investigation of a significant difference between in vivo and in vitro data is in progress.
1,2,3-Benzotriazin-4-ones and related systems. Part II. Thermolytic decomposition of substituted 1,2,3-benzotriazin-4-ones and isatoic anhydrides
Archer, John G.,Barker, Alan J.,Smalley, Robert K.
, p. 1169 - 1173 (2007/10/06)
Several nuclear-substituted 1,2,3-benzotriazin-4-ones have been thermolysed in an inert solvent. In each case the major identifiable product proved to be a 2-(o-aminophenyl)-3,1-benzoxazin-4-one. Nuclear-substituted isatoic anhydrides on thermolysis behaved similarly.
