| Abstract [eng] |
The aim of this work was to synthesize hydroxamic acids bearing 1,2,3,4-tetrahydroquinoline and to estimate their biological activity. During this project 6-bromo-1,2,3,4-tetrahydroquinoline was synthesized and Suzuki-Miyaura cross-coupling reactions were carried out to obtain various 6-aryl- 1,2,3,4-tetrahydroquinoline compounds. Interestingly, during Suzuki-Miyaura cross-coupling reaction small quantities of corresponding 6-arylquinolines were formed as by-products, which were successfully isolated. 1,2,3,4-Tetrahydroquinolines were alkylated with methyl and ethyl bromoacetate to obtain corresponding ester, which upon treatment with hydroxylamine hydrochloride afforded target hydroxamic acid derivatives bearing 1,2,3,4-tetrahydroquinoline moiety. Among tested hydroxamic acid derivatives, N-hydroxy-2-(6-(2-methoxyphenyl)-3,4-dihydroquinolin-1(2H)- yl)acetamide, N-hydroxy-2-(6-(3-methoxyphenyl)-3,4-dihydroquinolin-1(2H)-yl)acetamide and N-hydroxy-2-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)acetamide showed the most promising anticancer activity, while only N-hydroxy-2-(6-(2-methoxyphenyl)-3,4-dihydroquinolin-1(2H)- yl)acetamide showed good results against Streptococcus mutans and Lactobacilus acidophilus bacterial cultures. Interestingly, 6-arylquinolines, which were formed as side products during SuzukiMiyaura cross-coupling reactions, proved to possess good anticancer activity and effectively inhibited ABL kinase. |
