SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF NEW N-ETHYL-N-METHYL BENZENE SULFONAMIDE DERIVATIVES

This article describes the synthesis of some novel sulfonamide having the biologically active hydrazones 1,3,4-thiadiazoles and 4-oxothiazolidines moieties 2-4, 7 and 10-13 respectively. Starting with 4-acetyl-N-ethyl-N-methyl benzene sulfonamide (1). The structure of the newly synthesized compounds was confirmed by elemental analysis, IR, 1 HNMR and mass spectral data.


INTRODUCTION:-
Since resistance of pathogenic bacteria towards available antibiotics is rapidly becoming a major world wide problem, the design of new compounds to deal with resistant bacteria has become one of the most important areas of antibacterial research today.In addition, primary and opportunistic fungal infections continue to increase rapidly because of increased number of immouno-compromised patients.As known, not only biochemical similarity of human cell and fungi forms a handicap for selective activity but also the easily gained resistance is the main problem encountered in developing safe and efficient antifungal.(Basappa, et al., 2010), anti-cancer and anti-inflammatory (Reddy, et al., 2004), activities.
Cyclocondensation of compound 4 with an equiomolar ratio of ethylchloroaceate afforded the corresponding derivative 10, but when compound 4 was treated with two moles of ethyl chloroacetate under the same conditions gave derivative 11.The formation of 10, 11 were assumed to proceed via elimination of ethanol from intermediates derivatives, respectively.(Scheme 3).

MATERIALS AND METHODS
Bacillus subtilis (NCTC-1040), staphylococcus Aureus (NCTC-7447), Escherichia Coli, Candida Albicans (IMRu-3669) and Asperigillus Niger, were used against test compounds and obtained from the microbiology department, faculty of Pharmacy, Al-Azhar University.Chloramphenicol and terbinafine were used as a reference drugs and also obtained from the same source.

Agar diffusion test
Tall of nutrient agar were melted and poured each in an empty sterile petridishes and left for 24h.A specific culture of each organism was spread with a dry sterile swab on the surface of previously prepared plates.Sterile discs 6-9 mm diameter were impregnated with solutions of tested compounds, left to dry and were then placed on the surface of inoculated plate.Discs of antimicrobial standard were put in the culture of plate agar and inoculated at 37 o C for 24h.After inoculation the plates were examined visually and zone of inhibition were measured.
The microbiological testing of the newly synthesized compounds were performing in the department of microbiology, Faculty of Pharmacy, Al-Azhar University, Nasr City, Cairo, Egypt.

Table :
Antibacterial and antifungal activities