ORIGINAL RESEARCH Synthesis, FT-Raman, FT-IR, NMR spectroscopic characterization and antimicrobial activity of new mixed aza-oxo-thia macrocyclic compounds Naz Mohammed Aghatabay Æ Yaghub Mahmiani Æ Hu ¨seyin C ¸ evik Æ Fahrettin Gucin Æ Basaran Dulger Received: 22 November 2007 / Accepted: 20 August 2008 / Published online: 9 September 2008 Ó Springer Science+Business Media, LLC 2008 Abstract Series of new mixed aza-oxo-thia macrocyclic ligands {2,6,12,16-tetraaza-1,7,11,17-tetraoxo-9,19-dithia- [(4 0 -methyl-5 0 ,4,3 0 )(14 0 -methyl-15 0 ,14,13 0 )]ditriazine}cyc- locosane (L 1 ); {2,6,13,17-teraaza-1,7,12,18-tetraoxo-9,10, 20,21-tetrathia-[(4 0 -methyl-5 0 ,4,3 0 )(15 0 -methyl-14 0 ,16 0 ,15)] di-triazine}cyclodocosane (L 2 ); {2,6,14,18-tetraaza-1,7,13, 19-tetraoxo-10,22-dithia-[(4 0 -methyl-5 0 ,3 0 ,4)(16 0 -methyl-15 0 , 17 0 ,16)]ditriazine}cyclotetracosane (L 3 ) and {2,6,15,19-tet- raaza-1,7,14,12-tetraoxo-10,11,23,24-tetrathia-[(4 0 -methyl-5 0 , 4,3 0 )(17 0 -methyl-8 0 ,17,16 0 )]ditriazine}cyclohexa-cosane (L 4 ) were synthesized. The structural features of the compounds have been studied by elemental analyses, Mass, FT-Raman, FT-IR, 1 H and 13 C NMR spectroscopy. The antimicrobial activities of the ligands were evaluated using disk diffusion method in dimethyl sulfoxide as well as the minimal inhibitory concentration (MIC) dilution method, against 9 bacteria. The obtained results from disk diffusion method were assessed in side-by-side comparison with those of Penicillin-g, Ampicillin, Cefotaxime, Vancomy- cin, Oflaxacin, and Tetracyclin, well-known antibacterial agents. The results from dilution procedure were compared with Gentamycin as antibacterial and Nystatin as antifun- gal. The antifungal activities are reported on five yeast cultures namely Candida albicans, Kluyveromyces fragilis, Rhodotorula rubra, Debaryomyces hansenii, and Hanse- niaspora guilliermondii, and the results are referenced with Nystatin, Ketaconazole, and Clotrimazole, commercial antifungal agents. In most cases, the compounds show strong antifungal activity in the comparison tests. Keywords Disk-diffusion Á Dilution Á FT-Raman Á Gentamycin Á Inhibitory Á Tetracyclin Introduction For decades, the design and synthesis of macrocyclic compounds with hemo and hetero-multi-donor center have constituted one of the largest areas of research in organic and coordination chemistry [1–9]. Nature due to structural impact prefers certain macrocyclic derivatives for many fundamental biological functions, such as photosynthesis, storage and transport of oxygen in mammalian and other respiratory systems. In this respect, the macrocycles having various donor centers offer exciting possibilities to con- struct novel supramolecular assemblies that are capable of performing various specific molecular functions [10–13]. For instance, the precise molecular recognition between these compounds and their guests, mostly transition metal ions or biomolecules such as nucleic acids, proteins, pro- vides a good opportunity for studying key aspects of supramolecular chemistry, which are also significant in a variety of disciplines including bioorganic chemistry, bio- coordination chemistry, biology, medicine and related science and technology [14–19]. Macrocyclic compounds containing amide linkages and their transition metal com- plexes are found to be biologically interacting materials N. M. Aghatabay (&) Á Y. Mahmiani Á H. C ¸ evik Á F. Gucin Department of Chemistry, Fatih University, Bu ¨yu ¨kc ¸ekmece, Istanbul 34500, Turkey e-mail: natabay@fatih.edu.tr; natabay@yahoo.com B. Dulger Department of Biology, Canakkale Onsekiz Mart University, Canakkale, Turkey 123 Struct Chem (2008) 19:833–842 DOI 10.1007/s11224-008-9373-0