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Synthesis and Antiproliferative Activity against Cancer Cells of Indole-Aryl-Amide Derivatives.


ABSTRACT: Indoles constitute a large family of heterocyclic compounds widely occurring in nature which are present in a number of bioactive natural and synthetic compounds, including anticancer agents or atypical opioid agonists. As a result, exponential increases in the development of novel methods for the synthesis of indole-containing compounds have been reported in the literature. A series of indole-aryl amide derivatives 1-7 containing tryptamine or an indolylacetic acid nucleus were designed, synthesized, and evaluated as opioid ligands. These new indole derivatives showed negligible to very low affinity for μ- and δ-opioid receptor (OR). On the other hand, compounds 2, 5 and 7 showed Ki values in the low μM range for κ-OR. Since indoles are well known for their anticancer potential, their effect against a panel of tumor cell lines was tested. The target compounds were evaluated for their in vitro cytotoxicity in HT29, HeLa, IGROV-1, MCF7, PC-3, and Jurkat J6 cells. Some of the synthesized compounds showed good activity against the selected tumor cell lines, with the exception of IGROV1. In particular, compound 5 showed a noteworthy selectivity towards HT29 cells, a malignant colonic cell line, without affecting healthy human intestinal cells. Further studies revealed that 5 caused the cell cycle arrest in the G1 phase and promoted apoptosis in HT29 cells.

SUBMITTER: Zhao J 

PROVIDER: S-EPMC9822155 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

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Synthesis and Antiproliferative Activity against Cancer Cells of Indole-Aryl-Amide Derivatives.

Zhao Junwei J   Carbone Jacopo J   Farruggia Giovanna G   Janecka Anna A   Gentilucci Luca L   Calonghi Natalia N  

Molecules (Basel, Switzerland) 20221228 1


Indoles constitute a large family of heterocyclic compounds widely occurring in nature which are present in a number of bioactive natural and synthetic compounds, including anticancer agents or atypical opioid agonists. As a result, exponential increases in the development of novel methods for the synthesis of indole-containing compounds have been reported in the literature. A series of indole-aryl amide derivatives <b>1</b>-<b>7</b> containing tryptamine or an indolylacetic acid nucleus were de  ...[more]

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