A series of isoflavones was synthesized in high yields from 3-iodochromones via the Suzuki–Miyaura reaction. Selected isoflavones were then evaluated for potential anti-inflammatory and/or HIV reverse transcriptase inhibitory properties. Only 3-(4 $$'$$ ′ -methoxyphenyl)-4H-chromen-4-one 4b, 3-(4 $$'$$ ′ -chlorophenyl)-4H-chromen-4-one 4c and 3-(4 $$'$$ ′ -bromophenyl)-4H-chromen-4-one 4d showed dose-dependent attenuation of LPS-induced nitrate production indicating potential anti-inflammatory activity. NO production was 1.21, 1.43 and 1.43 $$\upmu \hbox {M}$$ μ M , respectively, even at the highest concentration of 50 $$\upmu \hbox {M}$$ μ M tested. However, relative to the positive control these activities are weak. None of the screened compounds was found to exhibit significant reverse transcriptase inhibition at the highest concentration of 50 $$\upmu \hbox {M}$$ μ M tested.