Synthesis and Cytotoxic Activity of Novel 3-methyl-1-[(4-substitutedpiperazin-1-yl)methyl]-1H-indole Derivatives

doi:10.1055/s-0032-1314868

Paper

Synthesis and Cytotoxic Activity of Novel 3-methyl-1-[(4-substitutedpiperazin-1-yl)methyl]-1H-indole Derivatives

Published Jun 29, 2012 · Meric Koksal, M. Yarim, I. Durmaz

Arzneimittelforschung/Drug Research

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Abstract

Abstract 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 (IC50) 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.

In Vitro Study

Study Snapshot

Novel 3-methyl-1-[(4-substitutedpiperazin-1-yl)methyl]-1H-indole derivatives show comparable anticancer activity to 5-fluorouracil and show apoptosis-inducing properties similar to paclitaxel.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Synthesis and Cytotoxic Activity of Novel 3-methyl-1-[(4-substitutedpiperazin-1-yl)methyl]-1H-indole Derivatives

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