Synthesis and anticancer effect of 3,4,5-n-alkyl-benzamides on colon carcinoma HCT- 116 cells

Jilly Octaria Tagore Chan, Ade Arsianti, Maurin Marcelia, Stevano Julio Wijoyo, Fadilah, Rista Putrianingsih, Norma Nur Azizah, Hiroki Tanimoto, Kiyomi Kakiuchi

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

The natural phenolic gallic acid has demonstrated a significant inhibition of cell proliferation in a series of cancer cell lines, as well as induced apoptosis in HCT-116 colon cancer cells. This research aims to synthesize six compounds of 3,4,5-trihydroxy-N-alkyl-benzamide derivatives of gallic acid, and investigate its anticancer effect on colon carcinoma HCT-116 cells.Six compounds of 3,4,5-trihydroxy-N-alkyl-benzamide, namely 3,4,5-trihydroxy-N-methyl-benzamide (2); 3,4,5-trihydroxy-N-ethyl-benzamide (3); 3,4,5-trihydroxy-N-butyl-benzamide (4); 3,4,5-trihydroxy-N-sec-butyl-benzamide (5); 3,4,5-trihydroxy-N-tert-butyl-benzamide (6) and 3,4,5-trihydroxy-N-hexyl-benzamide (7), have been successfully synthesized by amidation of carboxyl group of gallic acid with six corresponding alkylamines, respectively. Furthermore, anticancer effect of these six synthesized derivatives on colon HCT-116 cells were examined by MTT assay. Data were analyzed by linear regression method to generate IC50 value. The results will be compared with gallic acid as an original compound and doxorubicine as a positive control.Amidation of gallic acid with six corresponding alkylamines gave desired -N-methyl-, -N-ethyl-, -N-butyl-, -N-sec-butyl-, -N-ters-butyl-, and –N-hexyl benzamide with yield ranging from 18% to 84%. Compared to gallic acid (IC50: 0.05 µM) and doxorubicine (IC50: 0.001 µM), all these six synthesized derivatives showed a lower anticancer effect on colon HCT-116 cells. The strongest anticancer and inhibitory effect on HCT-116 cells has shown by 3,4,5-trihydroxy-N-hexyl benzamide (7) with IC50 value of 0.07 µM. Our results suggested that 3,4,5-trihydroxy-N-hexyl benzamide (7) is a potential to be developed as a promising anti-colon cancer agent.

Original languageEnglish
Pages (from-to)1362-1367
Number of pages6
JournalOriental Journal of Chemistry
Volume34
Issue number3
DOIs
Publication statusPublished - 1 Jan 2018

Keywords

  • 3,4,5-n-alkyl-benzamides
  • Anticancer
  • Gallic acid
  • HCT-116 cells
  • Synthesis

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