Osinubi, Adejoke published the artcileSynthesis and in vitro anticancer activities of substituted N-(4′-nitrophenyl)-L-prolinamides, Related Products of nitriles-buliding-blocks, the main research area is substituted nitrophenyl prolinamide preparation in vitro anticancer human; aryl proline preparation amine amidation; para fluoronitrobenzene thionyl chloride proline DMF catalyst condensation; anti-cancer agents; biomolecules; carcinoma cell lines; cytotoxicity; pyrrolidine-2-carboxamides.
Synthesis of N-(4′-substituted phenyl)-L-prolinamides I [R1 = CN, NO2; R2 = H, OH; R3 = H, Me, cyclohexyl, etc.; R4 = Pr, cyclohexyl, SO2C6H5, etc.; R3R4 = 4-morpholinyl, 2-isoindolinyl] via amidation reaction of N-aryl-L-prolines II with amines in presence of SOCl2 was described. Intermediate compounds II were obtained by condensation of p-fluoronitrobenzene with L-proline under aqueous-alc. basic conditions. The cytotoxicities of I 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 tumor inhibitory activities (79.50 ± 1.24%-50.04 ± 1.45%) against HepG2. I [R1 = NO2; R2 = H; R3 = R4 = n-butyl] exhibited the best anti-tumor activity against A549 with percentage cell inhibition of 95.41 ± 0.67% at 100μM. Likewise, I [R1 = NO2; R2 = H; R3 = Me; R4 = Ph] (70.13 ± 3.41%) and I [R1 = NO2; R2 = H; R3 = H; R4 = 4-NO2C6H4] (83.36 ± 1.70%) displayed stronger antineoplastic potencies against A549 than the standard, 5-fluorouracil (64.29 ± 2.09%), whereas I [R1 = NO2; R2 = H; R3 = R4 = n-butyl] (93.33 ± 1.36%) and I [R1 = NO2; R2 = H; R3 = H; R4 = 4-NO2C6H4] (81.29 ± 2.32%) outperformed the reference (81.20 ± 0.08%) against HCT-116. SGC7901 Showed lower percentage cell viabilities with I [R1 = NO2; R2 = H; R3 = H; R4 = 4-NO2C6H4] (8.02 ± 1.54%) and I [R1 = NO2; R2 = H; R3 = R4 = cyclohexyl] (27.27 ± 2.38%). These results underscored the antiproliferative efficacies of L-prolinamides while exposing I [R1 = NO2; R2 = H; R3 = H, Me; R4 = Ph, 4-NO2C6H4] as promising broad-spectrum anti-cancer agents. Structure-activity relationship studies were also discussed.
Royal Society Open Science published new progress about Amidation. 1885-29-6 belongs to class nitriles-buliding-blocks, name is 2-Aminobenzonitrile(Flakes or Chunks), and the molecular formula is C7H6N2, Related Products of nitriles-buliding-blocks.
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts