Turkish Journal of Chemistry
DOI
10.3906/kim-1604-2
Abstract
A series of novel positional oximes (2a-2d), $O$-methyl oxime ethers (3a-3d), and $O$-benzyl oxime ethers (4a-4d) were synthesized in high yields starting from their corresponding methyl 3-, 4-, 6-, and 13-keto tetradecanoates. The synthesized compounds were characterized by $^{1}$H NMR, $^{13}$C NMR, FT-IR, mass, and elemental analyses for their structures and $(E)$/$(Z)$ isomerizations. Their DNA binding abilities were investigated in vitro by agarose gel electrophoresis. The antibacterial and antifungal activities were tested also in vitro against eleven bacterial strains and three fungal strains. The relationship between the structure and the mentioned biological activities was discussed. Compound 2a showed good antibacterial activity against five types of bacteria. Compounds 2b, 2c, 2d, and 4d were effective against several microorganisms. Among these, 2a showed the best DNA binding, antibacterial, and antifungal activities. Therefore, 2a can be a pro-drug as an anticancer, antibacterial, and antifungal agent.
Keywords
Oxime, oxime ether, keto ester, DNA binding, antibacterial activity, antifungal activity
First Page
816
Last Page
829
Recommended Citation
KÜÇÜK, HATİCE BAŞPINAR; YUSUFOĞLU, AYŞE SERGÜZEL; AÇIK, LEYLA; AYDIN, BETÜL; and ARSLAN, LEYLA
(2016)
"Synthesis, ($E)$/($Z)$-isomerization, and DNA binding, antibacterial, and antifungal activities of novel oximes and $O$-substituted oxime ethers,"
Turkish Journal of Chemistry: Vol. 40:
No.
5, Article 11.
https://doi.org/10.3906/kim-1604-2
Available at:
https://journals.tubitak.gov.tr/chem/vol40/iss5/11
