The synthesis of chloraloses derivatives semicarbazones and thiosemicarbazones

Pentodialdo-1,4-furanoses (12-15) seperately reacted with semicarbazide and thiosemicarbazide compounds and such derivatives; 1,2-O-(R)-trichloroethylidene-α-D-xylo-pentodialdo-1,4-furanose semicarbazone (26), 1,2-O-(S)-trichloroethylidene-α-D-xylo-pentodialdo-1,4-furanose semicarbazone (27), 1,2-O-(S)-trichloroethylidene-β-L-arabino-pentodialdo-1,4-furanose semicarbazone (28), 1,2-O-(R)-trichloroethylidene-β-D-lyxo-pentodialdo-1,4-furanose semicarbazone (29) and 1,2-O-(R)-trichloroethylidene-α-D-xylo-pentodialdo-1,4-furanose thiosemicarbazone (30), 1,2-O-(S)-trichloroethylidene-α-D-xylo-pentodialdo-1,4-furanose thiosemicarbazone (31), 1,2-O-(S)-trichloroethylidene-β-L-arabino-pentodialdo-1,4-furanose thiosemicarbazone (32), 1,2-O-(R)-trichloroethylidene-β-D-lyxo-pentodialdo-1,4-furanose thiosemicarbazone (33) were synthesized in good yield. Their structures were elucidated on the basis of NMR, FTIR spectral analysis and elemental analysis. Furthermore, new compounds (26-33) were evaluated for their antimicrobial properties against some bacteria such as Escherichia coli, Staphylococcus aureus, Staphylococcus epidermidis, Pseudomonas aeroginosa, Bacillus cereus, Enterobacter aerogenes, Sarcina lutea, Salmonella typhimurium, Enterococcus faecalis, Candida albicans using the well diffusion and microdilution method. Antibacterial potency of the new compounds was evaluated using an inhibition zone diameter and MIC test. The results show that these compounds have a broad-spectrum of activity against Gram-positive, Gram-negative bacteria and fungicide Candida albicans. The MIC values were determined to be between 260 and 1510. Among all semicarbazone and thiosemicarbazone derivatives, it is determined that the compounds with the highest activity are compound 26 and 30 which are derivatized from xylochloralose with α stereochemistry.