296 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS A smaller number of compounds exhibited inhibitory activity against Candida albicans and Aspergillus niger. N-fi-D-Glucopyranosyl-N'-butylthiourea (II) was found to be most active and N-fi-D-glucopyranosyl-N'-dimethylaminothiourea (VII) was least active against Candida albicans. Against Aspergillus niger, also, compound II demonstrated the highest activity. The rest of the active compounds were found to be slightly active. N-fi-D-Glucopyranosyl-N'-benzylthiourea (V) exhibited slight activity against Escheri- chia coli and Pseudomonas aeruginosa. N-fi-D-Glycopyranosyl-l-piperidinethiocarbox- amide (VIII) showed activity against Pseudomonas aeruginosa, and N-fi-D-glycopyrano- syl-5-benzylidenerhodanine (X) was active against E. coil Other glucosylrhodanine derivatives did not show activity against either E. coli or P. aeruginosa, the Gram- negative organisms. Among the N-fi-D-glucopyranosyl-5-aralkylidenerhodanine derivatives, compound XII, having two chloro groups, was found to be active against three organisms: Staphylococcus aureus, Candida albicans, and Aspergillus niger. The monochloro derivative XI showed activity only against Staphylococcus aureus. None of the N- (2,3,4,6-tetra-0-acetyl-fi-D-glucopyranosyl)-5-aralkylidenerhodanine derivatives exhib- ited activity against any of the five organisms. Diethylamine, N-methylpiperazine, morpholine and thiomorpholine derivatives of glucosylthiourea had no antimicrobial activity. Also, methoxy, ethoxy, and hydroxy groups on the benzene ring of the glucosylrhodanine derivatives did not seem to confer any antimicrobial activity. However, the presence of chloro groups provided some antimicrobial activity, even though these derivatives were very poorly soluble in water. None of the tested compounds showed activity against all five organisms in comparison with rhodanine itself, the precursor of these compounds. However, II, III, IX, and XII were active against three organisms and V, VII and VIII exhibited activity against two of the organisms. It can be concluded that glycosylthioureas possess antimicrobial activities which tend to decrease with greater N-substitution on the NH2 group. In other words, the primary amine derivatives of glycosylthioureas show higher activities than derivatives of secondary amines. The presence of chloro groups in the benzene ring of glucosyl- 5-aralkylidenerhodanines appears to be necessary to provide antimicrobial activity with this type of compound. Glucosylthioureas showed relatively good activities against a Gram-positive organism, Staphylococcus aureus, and a yeast, Candida albicans, but poor activities against the Gram-negative organisms, Escherichia coli and Pseudomonas aeruginosa, and a mold, Aspergillus niger. Glucosyl-5-aralkylidenerhodanines exhibited a limited profile of antimicrobial activities. Toxicity levels of several of the glucosylthioureas were determined in mice, and the compounds were found to be remarkably non-toxic. Compounds II, V, VIII and IX were administered intraperitoneally up to a dose of 2000 mg/kg, and no deaths resulted. All animals survived the acute effects and appeared normal after a week. Soon after administration of the compounds, all animals showed decreased activity and labored respiration with the effects more pronounced at the higher dose. These effects disappeared within three hours. In comparison, rhodanine showed an LD50 of 164 mg/kg in mice (15).

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