Abstract
2-Amino-7-hydroxy-4-phenyl-4H-Chromene-3-carbonitrile (4) was synthesized through three-component reaction in ethanol/piperidine solution. Synthesis of several new 4H-chromenes (5-14) has been achieved involving various reactions. The structures of these new compounds were confirmed using infrared, proton nuclear magnetic resonance, and carbon-13 nuclear magnetic resonance as well as MS spectrometry. The structure activity relationship studies of the target compounds was in agreement with the in vitro essays and confirmed higher potent antimicrobial activity against some of the tested microorganisms. Antitumor activities of the target compounds were evaluated against three cancer cell lines HepG-2, HCT-116 and MCF-7 in comparison with 5-fluorouracil as reference drugs. The structure activity relationship study revealed that 2-amino-4-phenyl-3-(1H-tetrazol-5-yl)-4H-chromen-7-ol (13) was more beneficial than 8-hydroxy-2-methyl-5-phenyl-3,5-dihydro-4H-chromeno[2,3-d]pyrimidin-4-one (11), 8-hydroxy-2,5-diphenyl-3,5-dihydro-4H-chromeno[2,3-d]pyrimidin-4-one (12), and 8-hydroxy-5-phenyl-3,5-dihydro-4H-chromeno[2,3-d]pyrimidin-4-one (14) for antimicrobial and antitumor activity.