One-pot three-component synthesis of new triazolopyrimidine derivatives bearing indole moiety as antiproliferative agents

Abstract

A new series of triazolopyrimidine derivatives was produced via three-component reactions of suitable aromatic or heteroaromatic carboxaldehyde, 3-amino-1,2,4-triazole, and 3-indolyl-3-oxopropanenitrile in triethylamine as a catalyst. The new compounds have been interpreted using elemental analysis, infrared, mass spectrometry, and nuclear magnetic resonance spectroscopy. Antiproliferative effects of the new compounds have been screened on four human cancer types and one human noncancerous type (retinal pigment ephitilial-1) via the 3-(4,5-Dimethylthiazol-2-yl)-2,5-Diphenyltetrazolium Bromide assay. Compounds 4a and 4h have moderate activity against the human colon cancer; most of the compounds were active toward human lung cancer; compounds 4i, 4h, and 4g were highly active on hormone-dependent human breast cancer, while compounds 4c, 4b, 4h, and 4e were the most active on the hormone-independent human breast. The results of this study offer a source for further investigation of selected triazolopyrimidine derivatives as antiproliferative agents.