Synthesis and Biological Evaluation of 8‐Hydroxyquinoline‐hydrazones for Anti‐HIV‐1 and Anticancer Potential

Abstract

Abstract 8‐Hydroxyquinoline, being one of the privileged scaffolds, is known to possess a wide range of biological activities. 8‐Hydroxyquinoline quinoline has been explored synthetically through functionalization at different positions by different groups in search of medicinally important molecules. Herein, we synthesized twenty‐one ( 20 a‐20 u ) different hydrazones of 8‐hydroxyquinoline at C‐2 position in good yields and characterised by 1 H NMR, 13 C NMR, HRMS and IR. All the synthesized compounds were evaluated for their anti‐HIV‐1 and anti‐cancer potential through in vitro cell‐based assays. Compound 20 u ( ( E )‐2‐((2‐(4‐methoxyphenyl)hydrazono)methyl)quinolin‐8‐ol ) was found to be the most active against HIV (IC 50 : 1.88 and 6.27 μM; TI 73.82 and 22.07, against HIV‐1 VB59 and HIV‐1 UG070 respectively). Compound 20 l ( ( E )‐2‐((2‐(4‐fluorophenyl)hydrazono)methyl)quinolin‐8‐ol ) was identified as the most cytotoxic against four cancer cell lines (IC 50 : 26.30, 34.19, 38.77 and 34.23 μM against HeLa, MCF‐7, A‐549 and MDA‐MB‐231, respectively) with 2.4, 1.9, 1.6, 1.9‐folds selectivity, respectively over normal cells (IC 50 63.75 μM against HEK‐293 normal cells).