Synthesis and biological evaluation of novel 1,2,3-benzotriazin-4-one derivatives as leukotriene A4 hydrolase aminopeptidase inhibitors was written by Zhang, Fan;Wu, Dang;Wang, Gao-Lei;Hou, Shuang;Ping, Ou-Yang;Huang, Jin;Xu, Xiao-Yong. And the article was included in Chinese Chemical Letters in 2017.Formula: C7H7ClN2O This article mentions the following:
A series of novel 1,2,3-benzotriazin-4-one derivatives I [R = H, 6-O2N, 7-Cl, etc.; X = (CH2)n; n = 0, 1, 2, 3, 4] 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 I [R = 7-Cl; X = (CH2)4 (II)] exhibited the highest inhibitory activity up to 80.6% with an IC50 of 1.30 ± 0.20 μmol/L. The compound II was also tested for the proliferation inhibitory activities in THP1 human AML cell line and its binding model with LTA4H enzyme by mol. 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. In the experiment, the researchers used many compounds, for example, 6-Chloro-2-aminobenzamide (cas: 54166-95-9Formula: C7H7ClN2O).
6-Chloro-2-aminobenzamide (cas: 54166-95-9) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.Formula: C7H7ClN2O
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics