Browsing by Subject "Mannich base"
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Item Open Access Design, synthesis, and biological evaluation of indole-based 1,4-disubstituted piperazines as cytotoxic agents(2012) Akkoç Köksal, M.; Yüksel Yarım, M.; Durmaz, İrem; Atalay Çetin, RengülA series of 3-[(4-substitutedpiperazin-1-yl)methyl]-1H -indole derivatives were synthesized, and their structures were confirmed by spectral analysis. All the compounds were tested for their cytotoxic activity in vitro against 3 human tumor cell lines: human liver (HUH7), breast (MCF7), and colon (HCT116). Among the designed derivatives, most of the compounds showed significant cytotoxicity against liver and colon cancer cell lines with lower IC50 concentrations than the standard drug 5-fluorouracil. Compound 3s, with 3,4-dichlorophenyl substituent on the piperazine ring, was the most active in suppressing the growth of all screened cancer cells. © TÜBITAK.Item Open Access Synthesis and cytotoxic activity of novel 3-methyl-1-[(4-substitutedpiperazin-1-yl)methyl]-1 H-indole derivatives(Thieme, 2012) Koksal, M.; Yarim, M.; Durmaz, I.; Cetin Atalay, R.A series of novel 3-methyl-1-[(4-substitutedpiperazin-1-yl)methyl]-1H- indoles (3a-l) were synthesized and their cytotoxicities were analyzed against 3 different human cell lines, including liver (HUH7), breast (MCF7) and colon (HCT116). The Mannich reaction of 3-methylindole (1) with 4- substitutedpiperazines (2) and formaldehyde resulted to the 3-methyl-1-[(4- substitutedpiperazin-1-yl)methyl]-1H-indoles (3a-l) in 38-69% yields. The investigation of anticancer screening revealed that the tested compounds showed comparable activity to the reference drug 5-fluorouracil and compounds 3g, 3h, 3i and 3k, had lower 50% inhibition (IC 50) concentration than reference drug. Moreover, the cytotoxic effect of the most potent compound 3h on HUH7 and MCF7 cells through apoptosis was visualized by Hoechst staining and compared with paclitaxel, which is a mitotic inhibitor acting on microtubules. The morphological features of apoptosis were observed as condensed and fragmented nuclei that are similar to paclitaxel. © Georg Thieme Verlag KG Stuttgart.New York.