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 orheteroaromatic 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 magneticresonance spectroscopy. Antiproliferative effects of the new compounds have been screened on four human cancer types andone human noncancerous type (retinal pigment ephitilial-1) via the 3-(4,5-Dimethylthiazol-2-yl)-2,5-DiphenyltetrazoliumBromide assay. Compounds 4a and 4h have moderate activity against the human colon cancer; most of the compoundswere active toward human lung cancer; compounds 4i, 4h, and 4g were highly active on hormone-dependent human breastcancer, while compounds 4c, 4b, 4h, and 4e were the most active on the hormone-independent human breast. The resultsof this study offer a source for further investigation of selected triazolopyrimidine derivatives as antiproliferative agents.