Antibacterial, antifungal and cytotoxic properties of novel N-substituted sulfonamides from 4-hydroxycoumarin.
A new series of 4-({[2, 4-dioxo-2H-chromen-3 (4H)-ylidene] methyl} amino) sulfonamides have been obtained by the condensation reaction of 4-hydroxycoumarin with various sulfonamides (sulfanilamide, sulfaguanidine, p-aminomethyl-sufanilamide, p-aminoethylsufanilamide, sulfathiazole, sulfamethoxazole, sulfamethazine and 4-[(2-amino-4-pyrimidinyl) amino] benzenesulfonamide) in the presence of an excess of ethylorthoformate. These compounds were screened for their in-vitro antibacterial activity against four Gram-negative (E. coli, S. flexneri, P. aeruginosa and S. typhi) and two Gram-positive (B. subtilis and S. aureus) bacterial strains and for in-vitro antifungal activity against T. longifusus, C. albicans, A. flavus, M. canis, F. solani and C. glaberata. Results revealed that a significant antibacterial activity was observed by compounds (4) and (5), (6) and (8) against two Gram-negative, (P. aeruginosa and S. typhi) and two Gram-positive (B. subtilis and S. aureus) species, respectively. Of these (4) was found to be the most active. Similarly, for antifungal activity compounds (3) and (8) showed significant activity against M. canis and, (6) and (8) against F. solani. The brine shrimp bioassay was also carried out to study their in-vitro cytotoxic properties and only two compounds, (4) and (8) possessing LD50 = 2.9072 x 10(-4) and 3.2844 x 10(-4) M, respectively, displayed potent cytotoxic activity against Artemia salina
Chohan
Zahid H
ZH
Department of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan. zchohan@mul.paknet.com.pk
Shaikh
Ali U
AU
Rauf
Abdul
A
Supuran
Claudiu T
CT
D015110:4-Hydroxycoumarins / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D000935:Antifungal Agents / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D003603:Cytotoxins / Q000737:chemistry / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D013449:Sulfonamides / Q000138:chemical synthesis / Q000494:pharmacology* / Q000633:toxicity
D015110:4-Hydroxycoumarins; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D003603:Cytotoxins; D004791:Enzyme Inhibitors; D013449:Sulfonamides; C068805:4-hydroxycoumarin