Synthesis and anticancer activities of substituted -(4'-nitrophenyl)-l-prolinamides.

Prolinamides are present in secondary metabolites and have wide-ranging biological properties as well as antimicrobial and cytotoxic activities. -(4'-substituted phenyl)--prolinamides - were synthesized in two steps, starting from the condensation of -fluoronitrobenzene - with -proline -, under aqueous-alcoholic basic conditions to afford -aryl--prolines -, which underwent amidation via a two-stage, one-pot reaction involving SOCl and amines, to furnish -prolinamides in 20-80% yield. The cytotoxicities of - against four human carcinoma cell lines (SGC7901, HCT-116, HepG2 and A549) were evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay; with good tumour inhibitory activities (79.50 ± 1.24%-50.04 ± 1.45%) against HepG2. exhibited the best anti-tumour activity against A549 with percentage cell inhibition of 95.41 ± 0.67% at 100 µM. Likewise, (70.13 ± 3.41%) and (83.36 ± 1.70%) displayed stronger antineoplastic potencies against A549 than the standard, 5-fluorouracil (64.29 ± 2.09%), whereas (93.33 ± 1.36%) and (81.29 ± 2.32%) outperformed the reference (81.20 ± 0.08%) against HCT-116. SGC7901 showed lower percentage cell viabilities with (8.02 ± 1.54%) and (27.27 ± 2.38%). These results underscore the antiproliferative efficacies of -prolinamides while exposing and as promising broad-spectrum anti-cancer agents. Structure-activity relationship studies are discussed.