Eighteen new aryl sulphonamoyl ‘Phe-Gly’-dipeptide carboxamide derivatives were synthesized, characterized and investigated for their in-silico and in vitro properties. The base mediated reaction of L-phenylalanine with para-nitrobenzenesulphonylchloride, para-toluenesulphonylchloride and benzenesulphonylchloride was successfully carried out to produce the respective benzenesulphonamide intermediates (3a-c). This was followed by the protection of the amino group of glycine (4) with tert-butyloxycarbamate (Boc) using a solution of di-tert-butyldicarbonate in 1, 4-dioxane at 5^oC to obtain (5). Amidation reaction of the Boc-protected glycine with six amines 4-aminophenol, 1-H-indole, 1-H-imidazole, guanine, adenine and cytosine yielded the respective Boc-protected carboxamides (7a-f). The carboxamides formed were then deprotected using DCM/trifluoroacetic acid (TFA; 1:1%) for 1 hour to yield (8a-f). The reaction of the deprotected carboxamides with benzenesulphonamide and substituted benzenesulphonamides in the presence of amide coupling partners 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC.HCl) and 1-hydroxylbenzotriazole (HOBt) at room temperature yielded the eigtheen ‘Phe-Gly’-dipeptide carboxamide target molecules (9a-r) in 39-95% yields. The synthesized compounds were characterized using Fourier Transformed Infrared (FTIR), and Nuclear Magnetic Resonance (¹H and ¹³C NMR). Computational studies were also carried out to determine their antibacterial, antifungal, anti-convulsant, anti-diuretic, anti-insomnia, anti-leishmaniasis and anti-leukamia potentials. All the compounds showed good binding.  The binding energies (kcal/mol) for anti-bacteria, antifungal,  antileishmaniasis, anticonvulsant, antidiuretic, antiinsomnia and antileukaemia were -7.0 to -7.6, -8.1 to -10.1, -9.4 to -9.8, -8.0 to -8.1, -10.1 to  -10.4, -10.4 to -10.8 and -7.0 to -7.7 respectively. Antimicrobial study was carried out to determine the activities of the compounds against Pseudomonas aeruginosa, Staphylococcus aureus, Streptococcus pyogene, Escherichia coli and Candida albicans. The Inhibitory zone diameter (IZD) values were 3-13 mm. The Minimum Inhibitory Concentration (MIC) values in (mg/m) were 1.485 – 15.848 and the Minimum Bactericidal Concentration (MBC) values (mg/m) were 12.500 – 25.500.  The compounds showed their highest activities towards Staphylococcus aureus.