K₂CO₃-nanoparticles catalyzed the synthesis of 3-arylidine imidazo[1,2-c]pyrimidine candidates: Cytotoxic activity and docking study

Abstract

The present work describes an green and eco-friendly synthetic protocol, and vitro anti-proliferative activity of a new series of 3-arylidine imidazo[1,2-c]pyrimidines. The target molecules 4a–p were synthesized via one-pot cyclization of 6-amino-4-(4-chlorophenyl)-2-thioxo-1,2-dihydropyrimidine-5-carbonitrile(1) with chloroacetyl chloride followed by condensation with a series of aromatic and heteroaromatic aldehydes in the presence of K₂CO₃-NPs at room temperature. The high yield (80–96%), mild reaction conditions (short reaction time and no heat needed), simple purification, and soft, cheap, high efficiency readily available and stability of K₂CO₃-NPs are evident features of the present approach. Pyrimidines 4c, 4 g and 4i demonstrated significant anti-proliferative activity against MCF-7 especially compound 4i was found to be the most effective among the tested compounds with IC₅₀ values 3.83 µg/ml in MCF-7 cell line compared to the standard drug doxorubicin. In addition, compounds 4b, 4c, 4d, 4i, and 4n demonstrated high cytotoxic activity against HCT116, particularly compound (4b) was the most potent among the tested compounds with IC₅₀ values 9.3 µg/ml in HCT116 cell line compared to doxorubicin.

Graphical Abstract

Keywords:

• Cytotoxic and molecular docking
• imidazo[1,2-c]pyrimidine
• K₂CO₃-NPs

Correction Statement

This article has been corrected with minor changes. These changes do not impact the academic content of the article.