Thiazole derivatives, which are representative by sulfurol, 4-methyl-5-hydroxyethyl-thiazole, are well known as perfumes of food additives in the food industry and have been widely utilized as antibiotics in the medical industry. One of the commercial antimicrobial agents, 2-(4-thiazolyl)benzimidazole (TBZ), based on the thiazole skeleton has fungicidal activity, which is used for the antimicrobial treatment of products such as foods, textiles, papers and synthetic resins. However, this compound shows a weak antibacterial activity.1) The N-alkyl-5-(2-hydroxyethyl)-4-methylthiazolium iodide (T-n,n: alkyl chain length), quaternized the sulfurol with long alkyl groups, successfully acquired a wide antimicrobial activity for both bacteria and fungi, and was a more effective fungicide than TBZ.2) In recent years, 4-methylthiazolium betaine also has been reported to show a significant antibacterial activity under hyperosmotic conditions.
3)Gemini quaternary ammonium compounds (gemini QACs) are linking two molecules of tertiary amines-quaternarized compounds (mono-QACs), which are famous as significant antimicrobial agents in clinical applications, food production and health care, with hydrocarbon chains. The gemini QACs possess a unique structure, a greater surface activity and greater antimicrobial potency than conventional mono-QACs. Chemists have studied their physicochemical properties [4][5][6] and greater effective antibacterial potency than the corresponding mono-QACs. [7][8][9] We have also described the syntheses of gemini QACs, which have two cationic pyridiniums, and discussed their antimicrobial activities and characteristics. [10][11][12][13][14][15] It has been proved that the antimicrobial potency of their gemini QACs shows a wider and more effective spectrum than that of mono-QACs against both gram-negative and gram-positive bacteria and fungi. 4,4Ј-(a,w-Polymethylenedithio)bis(1-alkylpyridinium iodide) (4DTBP-m,n, m: methylene chain length, 3, 4, 6, 8 or 10; n: 8, 10, 12, 14, 16 or 18) as the gemini QACs was studied in great detail. The antimicrobial activity was not only wider and stronger than that of the usual mono-QACs, N-dodecylpyridinium iodide and benzyldimethyldodecylammonium chloride (BAC), but also independent of pH, temperature and molecular hydrophobicity, the characteristics of which were different from those of mono-QACs.10,11) Sumitomo et al. revealed the leakage of magnesium ion stabilizing the outer membrane of bacterial cells and that of ATP from the cells, and then the respiratory inhibition before bacterioclastic action by treatment of 4DTBP-6,8 toward Escherichia coli (E. coli) IFO 12713. This result suggested that gemini QACs conform to a specific bactericidal mechanism unlike mono-QACs.16) The structural feature of 4DTBP-m,8, which affected the length of the methylene chain, was examined on the basis of the transitions of the conformer and solvation free energy during their holding processes.
17)In this study, we focused on 5,5Ј-[2,2Ј-(1,4-tetramethylnedicarbonyldioxy)diethyl]b...