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Peer-reviewedCC BYRSC advances

Design and synthesis of 3-(1H-indol-3-yl)-N-(3,4,5-trimethoxyphenyl) acrylamide derivatives as anticancer agents.

  • Seyedeh Niloufar Ghafouri1
  • Parviz Rashidi Ranjbar1
  • Mohammad Mahdavi2
  • Aida Iraji3,4
4 affiliations
  1. 1School of Chemistry, College of Science, University of Tehran Tehran Iran [email protected].
  2. 2Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences Tehran Iran.
  3. 3Stem Cells Technology Research Center, Shiraz University of Medical Sciences Shiraz Iran [email protected] [email protected].
  4. 4Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences Shiraz Iran.
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Abstract

In this study, a new series of indole-based trimethoxy aniline hybrids (10a-o) was designed through a fragment-based hybridization strategy and synthesized via a multistep synthetic procedure. The cytotoxicity of the synthesized compounds was evaluated against human breast cancer cell lines (MCF-7 and MDA-MB-468), hepatocellular carcinoma cells (Hep-G2), and the non-cancerous HEK-293 cell line using MTT assay. Several analogs exhibited moderate antiproliferative activity, and compound 10b, bearing an ortho-methyl substituent, emerged as the most active derivative against MCF-7. Structure-activity relationship (SAR) analysis revealed that ortho-alkyl substituents favored selectivity toward MCF-7 cells, whereas 4-Br substitution and ethyl-alkyl extension preferentially enhanced activity against Hep-G2 cells. Mechanistic studies demonstrated that 10b primarily induced apoptotic cell death at lower concentrations and exposure times, whereas higher concentrations and prolonged treatment resulted in more necrotic cell death. Compound 10b also induced dose-dependent alterations in cell-cycle progression in MCF-7 cells, characterized by S-phase arrest.

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Cite

BibTeXRIS
BibTeX
@article{ghafouri2026design,
  title = {{Design and synthesis of 3-(1H-indol-3-yl)-N-(3,4,5-trimethoxyphenyl) acrylamide derivatives as anticancer agents.}},
  author = {Seyedeh Niloufar Ghafouri and Parviz Rashidi Ranjbar and Mohammad Mahdavi and Aida Iraji},
  journal = {RSC advances},
  year = {2026},
  month = oct,
  doi = {10.1039/d6ra03896d},
  url = {https://europepmc.org/article/MED/42923786},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Design and synthesis of 3-(1H-indol-3-yl)-N-(3,4,5-trimethoxyphenyl) acrylamide derivatives as anticancer agents.
AU  - Seyedeh Niloufar Ghafouri
AU  - Parviz Rashidi Ranjbar
AU  - Mohammad Mahdavi
AU  - Aida Iraji
PY  - 2026
DA  - 2026/10/22
JO  - RSC advances
DO  - 10.1039/d6ra03896d
UR  - https://europepmc.org/article/MED/42923786
AB  - In this study, a new series of indole-based trimethoxy aniline hybrids (10a-o) was designed through a fragment-based hybridization strategy and synthesized via a multistep synthetic procedure. The cytotoxicity of the synthesized compounds was evaluated against human breast cancer cell lines (MCF-7 and MDA-MB-468), hepatocellular carcinoma cells (Hep-G2), and the non-cancerous HEK-293 cell line using MTT assay. Several analogs exhibited moderate antiproliferative activity, and compound 10b, bearing an ortho-methyl substituent, emerged as the most active derivative against MCF-7. Structure-activity relationship (SAR) analysis revealed that ortho-alkyl substituents favored selectivity toward MCF-7 cells, whereas 4-Br substitution and ethyl-alkyl extension preferentially enhanced activity against Hep-G2 cells. Mechanistic studies demonstrated that 10b primarily induced apoptotic cell death at lower concentrations and exposure times, whereas higher concentrations and prolonged treatment resulted in more necrotic cell death. Compound 10b also induced dose-dependent alterations in cell-cycle progression in MCF-7 cells, characterized by S-phase arrest.
SN  - 2046-2069
ER  -