Synthesis, antifungal activities, and potential detoxification of N-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)thiocarbamates.
A series of N-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)thiocarbamates were synthesized by the reaction of glucosyl isothiocyanates with monohydric and dihydric alcohols, and acetone oxime, using methods of both normal reaction and microwave-assisted synthesis. Antifungal activities of the title compounds were determined with three kinds of plant pathogenic fungi, Fusarium graminearum, Rhizoctoria cerealis, and Colletotrichum orbiculare. The synthesized glucosyl thiocarbamates easily reacted with HgCl(2) to give novel metal-organic compounds, bis[O-alkyl N-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)thiocarbamato]mercury, in yields of 80%. This strong affinity of thiocarbamates for mercury showed their potential utility in medical or marine environmental detoxification.
Zhou
Yaling
Y
Department of Chemistry, College of Science, Nanjing Agricultural University, Nanjing 210095, China.
Wang
Li
L
Han
Lixia
L
Meng
Fangui
F
Yang
Chunlong
C
D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects*; D008627:Mercuric Chloride / Q000737:chemistry* / Q000633:toxicity; D013859:Thiocarbamates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000935:Antifungal Agents; D013859:Thiocarbamates; D008627:Mercuric Chloride