– Synthesis and Evaluation for Biological Activities of N– Pyridin-3-Yl Substituted [Phenylsulphonamido] Acetamide –
ABSTRACT
In this study, a series of N-pyridine-3-yl substituted [phenylsulphonamido] acetamide has been synthesized.
The reaction of phenylsulphonyl chloride with various amino acids in a basic medium yielded phenylsulphon amido alkanoic acid which, on chlorination with thionyl chloride, gave acid chloride derivatives of phenylsulphon amido alkanoic acid in situ.
The acid chloride derivatives on condensation with 3-aminopyridine gave corresponding acetamide in good to excellent yield. The compounds were characterized by FTIR, 1H-NMR, and 13C- NMR and screened for antibacterial, antifungal, and antioxidant activities.
The result revealed that the compounds possess antibacterial activities. One of the compounds, 2- [(phenylsulfonyl)amino]propanoic acid had better antibacterial activities than ciprofloxacin the reference drug while others are less active.
All the compounds have less antifungal activities than ketoconazole the reference drug. 2- [(phenylsulfonyl)amino]propanoic acid had the best antioxidant properties of all the compounds.
INTRODUCTION
Background of Study
The growing incidence of microbial resistance to currently used antibiotics represents a serious medical problem.
Therefore, there is an urgent need to develop new classes of therapeutic agents to treat microbial infections. Such a new therapeutic agent has to exhibit a wide spectrum of biological activities.
The basic sulphonamide group [SO2, NHR] occurs in various biologically active compounds including antimicrobial drugs, antithyroid agents, antitumors, antibiotics, and inhibitors of carbonic anhydrase2.
Sulphonamides are widely used to treat microbial infections by inhibiting the growth of Gram-negative and Gram-positive bacteria, some protozoa, and fungi3. Clinically, sulphonamides are used to treat several urinary tract infections and gastrointestinal infections4.
Sulphonamides5 that are aromatic or heteroaromatic are responsible for the inhibition of the growth of tumour cells. They act as antitumor agents by inhibiting carbonic anhydrase activity.
They are structurally similar to p– aminobenzoic acid (PABA) which is a cofactor that is needed by the bacteria for the synthesis of folic acid.
Sulphonamide antibiotics inhibit the conversion of PABA into folic acid and thus ultimately inhibit the synthesis of DNA. They are also used in veterinary medicine to treat infections in livestock6.
REFERENCES
Hansey C., Sammes, P.G. Taylor, J.B. (1990): In comprehensive medicinal chemistry; pergamon press. Oxford, vol.
Perlorich G.L., Strakhorg N.N., Kazacharko V.P., Volkous T.V., Trailor V.V., Schaper K.J., Racusky O.A.,(2008): Sulfonamides as a subject to study molecular interactions in crystals and solutions: sublimation, solubility, solvation, distribution and systel structure, Lut; J. Pharu, 349(1– 2); 300-313.
Gaded A.K., Malajanshetti L.S., Nimbalkar S., Raichurrar A., (2000): Synthesis and antibacterial activity of some 5 – granthydrazone/thiocyenato- 6 – aylimidazo (2, 1 – 6) – 1, 3, 4 – thiadazole – sulforanide derivatives,Eur. J. Med. Chem, 35(9); 853-857.
EL S., Ayed N.S., EL R.E., EL – Ashry S.M., EL – Kerdawy M.M., (2011): Synthesis and antifunor aitrity of new sulfornamide derivatives of thigdeizolo (3,2-9) pyrimidines, J. Med chem, 46 (9); 3714-3720.
Garai – Galar M.J., Diaz-craz M.S., Bercelo D.,(2008): Identificaiton and dethmination of metabolites and degradation products of sulfonamides antibiotics. Trends anal. Chem, 27(11); 1008 –
CLSI (The clinical laboratry standard institutes): Agar dilution and disk diffusion susceptibility festins of cargylobacter SPP, (2010): Journal of clinical microbiology, 45(8): 2758 –
Join Our Newsletter!
Don’t miss this opportunity
Enter Your Details
Be the first to comment