Synthetic Studies and Antibacterial Activity of Nucleobases and their N- and S-Glucosides from 2-Amino Benzoic Acid and its Benzamido Derivatives

A series of S-glucosides 11a-14a and their benzamido derivatives 11b-14b have been synthesized by reacting D-glucose with thiol groups of 5-(2’-aminophenylene)-1,3,4-oxadiazole-2thioles 7(a,b), 5-(2’-aminophenylene)-1,3,4-thiadiazole-2-thiols 8(a,b), 5-(2’-aminophenylene)-1,2,4triazole-3-thiols 9(a,b) and 5-(2’-aminophenylene)-4-N-amino-1,2,4-triazole-3-thiols 10(a,b). The thiols 7(a,b)-10(a,b) have been synthesized from hydrazides 3(a,b) which already been synthesized from 2-aminobenzoic acid and its benzamido derivative. All synthesized compounds were characterized by IR, UV,1Hand13CNMR. Nucleobases and a representative of S-glycoside were tested in vitro against the following microorganisms: two Gram-positive bacteria Staphylococcus aureus and Bacillus cereusand two Gram-negative bacteria Escherichia coli, Pseudomonas aeruginosa and they exhibited significant effects. Amykacine was used as positive standard.