A metal‐free aryl amination reaction of aryl halides and amino acids; with the amino acid serving as the nucleophilic aminating agent, is reported. The reaction was achieved by the condensation of various aryl halides 1 with cyclic and acyclic amino acids 2, in the presence of a cheap and readily available base, potassium carbonate, in refluxing ethanol/water solution (1 : 1) for 3 h, under simple operating conditions. The products, N‐(p‐substituted phenyl)‐amino‐2‐carboxylic acids 3–12, were obtained in isolated yields of 25–90% and characterized by IR, 1H‐ and 13C‐NMR spectroscopy and high‐resolution mass spectrometry. These arylated amino acids are vital synthons and precursors to many compounds of physiological importance.

Prolinamides are present in secondary metabolites and have wide-ranging biological properties as well as antimicrobial and cytotoxic activities. N -(4′-substituted phenyl)- l -prolinamides 4a – 4w were synthesized in two steps, starting from the condensation of p -fluoronitrobenzene 1a – 1b with l -proline 2a – 2b , under aqueous–alcoholic basic conditions to afford N -aryl- l -prolines 3a – 3c , which underwent amidation via a two-stage, one-pot reaction involving SOCl 2 and amines, to furnish l -prolinamides in 20–80% yield. The cytotoxicities of 4a – 4w 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. 4a exhibited the best anti-tumour activity against A549 with percentage cell inhibition of 95.41 ± 0.67% at 100 µM. Likewise, 4s (70.13 ± 3.41%) and 4u (83.36 ± 1.70%) displayed stronger antineoplastic potencies against A549 than the standard, 5-fluorouracil (64.29 ± 2.09%), whereas 4a (93.33 ± 1.36%) and 4u (81.29 ± 2.32%) outperformed the reference (81.20 ± 0.08%) against HCT-116. SGC7901 showed lower percentage cell viabilities with 4u (8.02 ± 1.54%) and 4w (27.27 ± 2.38%). These results underscore the antiproliferative efficacies of l -prolinamides while exposing 4a and 4u as promising broad-spectrum anti-cancer agents. Structure-activity relationship studies are discussed.

The resistance of bacteria to current antibiotic drugs and the re-occurrence of different ailments after several therapeutic protocols continue to be a cause for concern. Arylated amino acids are vital synthons to many compounds; they serve as essential building blocks in the synthesis of nitrogen heterocycles with various biological activities. This research reports on the synthesis of some N-aryl amino acids and evaluates their antibacterial activities. The N-aryl amino acids 3a–3j were obtained by reacting different 4-substituted fluorobenzene 1a–1d with different amino acids 2a–2g via a metal-free base-induced aryl amination reaction of aryl halides. The antibacterial activities of the synthesized compounds were evaluated against eight bacterial strains (Four Gram-positive, Bacillus subtilis (ATCC 6633), Streptococcus pneumonia (ATCC 33400), Staphylococcus aureus (ATCC 25923), and Staphylococcus epidermidis (ATCC 14990), and four Gram-negative, Enterobacter cloacae (ATCC 43560), Escherichia coli (ATCC 25922), Proteus mirabilis (ATCC 43071), and Klebsiella oxytoca (ATCC 13182) using the agar well diffusion method with streptomycin as a reference drug. The biological screening indicates that the synthesized compounds 3a, 3e, and 3j have promising broad-spectrum antibacterial potential, as the N-aryl amino acid displayed activity that was comparable to the standard drug against Streptococcus pneumonia, Escherichia coli, and Proteus mirabilis.