Synthesis, FT-Raman, FT-IR, NMR spectroscopic characterization and antimicrobial activity of new mixed aza-oxo-thia macrocyclic compounds

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-tetraaza-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, Vancomycin, Oflaxacin, and Tetracyclin, well-known antibacterial agents. The results from dilution procedure were compared with Gentamycin as antibacterial and Nystatin as antifungal. The antifungal activities are reported on five yeast cultures namely Candida albicans, Kluyveromyces fragilis, Rhodotorula rubra, Debaryomyces hansenii, and Hanseniaspora 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.

Synthesis, spectroscopic characterization and density functional studies of a bis-benzimidazole derivative and of its complexes with palladium(II) halides

“…The multifunctional features of bis-benzimidazole and its derivatives have received considerable attention as a result of the significant roles they played as ligands in coordination chemistry [1][2][3], medicinal chemistry as antimicrobial [3][4][5][6], antitumor agents [7][8][9] and for applications, such as dyes and in the field of photography [10][11][12].…”

A Three-Coordinate Ag(I) Complex Based on the V-Shaped Ligand 1,3-Bis(1-Ethylbenzimidazol-2-Yl)-2-Thiapropane: Synthesis, Crystal Structure and DNA-Binding Properties

“…The IR spectrum of the ligand 1 shows characteristic absorption bands of the benzimidazole group at 1274 and 1458 cm -1 , which can be assigned to ν (C-N) and ν (C=N) , respectively. 49,50 For the complex 2, these stretching frequencies are red shifted to 1180 cm -1 and 1430 cm -1 , respectively, which implies direct coordination of nitrogen atoms to metal ions.…”

Synthesis of Novel Amide Derivatives with In Vitro Antiproliferative and Cytotoxic Activity

“…Amide compounds are also widely used in medical, industrial, and agricultural areas. The effects of macrocyclic polyamines on the reactive oxygen species level, apoptosis events, cellular viability, and activity of antioxidant enzymes that were assessed in some mammalian cell cultures have been reported . The synthesis of amides and the study on their biological activity have been an area of wide interest and diversity in recent years .…”