Synthesis and biological evaluation of sulfonamide thiazole and benzothiazole derivatives as antimicrobial agents

Iro Argyropoulou; Athina Geronikaki; Paola Vicini; Franca Zani

doi:10.3998/ark.5550190.0010.611

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Synthesis and biological evaluation of sulfonamide thiazole and benzothiazole derivatives as antimicrobial agents

Iro Argyropoulou; Athina Geronikaki; Paola Vicini; Franca Zani

Volume 2009, Issue 6, Commemorative Issue in Honor of on the occasion of , pp. 89-102

DOI: http://dx.doi.org/10.3998/ark.5550190.0010.611

Paper ID: HP-3516MP

Received on 2008-09-16; Accepted on 2009-01-26; Published on 2009-02-04

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Issue in Honor of Prof Henk C. van der Plas ARKIVOC 2009 (vi) 89-102 Synthesis and biological evaluation of sulfonamide thiazole and benzothiazole derivatives as antimicrobial agents Iro Argyropoulou,a Athina Geronikaki,a* Paola Vicini,b and Franca Zanib aDepartment of Pharmaceutical Chemistry, School of Pharmacy, Aristotelian University of Thessaloniki, Thessaloniki 54006, Greece bDipartimento Farmaceutico, Universita` degli Studi di Parma, Viale G. P. Usberti 27/A, Parma 43100, Italy E-mail: [email protected] Dedicated to 80th anniversary of Prof. Henk Van der Plas Abstract Several thiazoles and benzothiazoles carrying a benzenesulfonamide moiety at position 2 of the heterocyclic nucleus were synthesised and tested as antimicrobial agents. All sulfanilamides and some of the nitro substituted sulfonamides have effective antibacterial properties against Gram positive bacteria (MIC 0.3-100 µg/mL) such as several bacilli, staphylococci and streptococci, including methicillin-resistant Staphylococcus aureus and Staphylococcus epidermidis strains. On the contrary, no inhibition of Gram negative Escherichia coli and fungi is detected up to the concentration of 100 µg/mL. Synergistic inhibitory activity occurs when the active antibacterial sulfonamides are tested in combination with trimethoprim against both Bacillus subtilis and Staphylococcus aureus. Keywords: Thiazole derivatives, benzothiazole derivatives, sulfonamides, antimicrobial activity Introduction It is well-known that the thiazolyl group is of great importance in biological systems. Alkyl/arylaminoacetyl derivatives of 2-amino-4-phenylthiazolyl,1 2-aminobenzothiazolyl,2 2amino( substituted)-benzothiazolyl,3 2-phenylamino-4-phenylthiazolyl,4 2-amino-4methylthiazolyl, 5 as well as 3-aminobenzo[d]isothiazole derivatives6 were found to have a potent local anaesthetic activity. Anti-inflammatory, analgesic, and antipyretic activities for some thiazolyl and benzothiazolyl derivatives are also known.7,8 On the other hand, sulfonamides have a variety of biological activities such as antibacterial,9-11 insulin releasing,12 carbonic anhydrase inhibitory,13,14 anti-inflammatory,15 and ISSN 1551-7012 Page 89 ©ARKAT USA, Inc.