Yeni ftalamit türevlerinin sentezi ve biyolojik aktivitelerinin incelenmesi

In this thesis, eighteen novel derivatives of N1,N2-bis[(2-substitutedphenyl)ethyl]phthalamide (compounds 1-11) and 3-nitro-N1,N2-bis[(2-substitutedphenyl)ethyl]phthalamide (compounds 12-22) were synthesized to screen their biological activities as shown in Table 1.1. The target compounds (compounds 1-11); N1,N2-bis[(2-substitutedphenyl)ethyl]phthalamide were obtained by the reaction of phthalic anhydride and phenylethylamine derivatives in ethanol. 3-nitro-N1,N2-bis[(2-substitutedphenyl)ethyl]phthalamide (compounds 12-22) were also synthesized by the reaction of 3-nitrophthalic anhydride and phenylethylamine derivatives in methanol. Structure identification of synthesized compounds was elucidated by IR, UV, 1H-NMR, 13C-NMR, and elemental analysis. Antimicrobial activities of the compounds were examined by the conventional agar dilution method. Anticancer activities of the compounds were studied by MTT assay. Synthesized compounds were screened against gram-positive bacteria strain of Staphylococcus aureus and gram-negative bacteria strains of Escherichia coli and Pseudomonas aeruginosa with the conventional agar dilution method. Synthesized compounds generally showed moderate or low activity compared with Ofloxacin as a reference drug. N1,N2-bis[2-(4-chlorophenyl)ethyl]phthalamide (compound 4), 3-nitro-N1,N2-bis[2-(2-chlorophenyl)ethyl]phthalamide (compound 13), 3-nitro-N1,N2-bis[2-(4-chlorophenyl)ethyl]phthalamide (compound 15) and 3-nitro-N1,N2-bis[2-(2,4-dichlorophenyl)ethyl]phthalamide (compound 16) exhibited the highest zone of inhibition value against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa with moderate antibacterial activities with minimum inhibitory concentration of 25 µg/ml. Synthesized compounds generally showed moderate or no cytotoxic activity. Among the synthesized compounds (compounds 1-11), N1,N2-bis[2-(2,4-dichlorophenyl)ethyl]phthalamide (compound 5) was the most active compound against MCF7 (human breast cancer cell line) and Hep3B (human liver cancer cell line) cancer cell lines with IC50 values of 87.6 and 49.6 μM. From the synthesized compounds (compounds 12-22), 3-nitro-N1,N2-bis[2-(2,4-dichlorophenyl)ethyl]phthalamide (compound 16) and 3-nitro-N1,N2-bis[2-(2-fluorophenyl)ethyl]phthalamide (compound 17) presented the highest activity against MCF7 and Hep3B cancer cell lines with IC50 values of 46.0, 45.1, 50.5 and 37.6 μM, respectively.