ABSTRACT
Glucosidation of the new 8-amino-6-benzyl(or substituted benzyl)-2,8-dihydro-1,2,4-triazolo[4,3-b][1,2,4]triazin-7(3H)-ones (3a-d) with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide 4 gave the corresponding N-glucosides 5a-d. Chemical transformations leading to new functionalities have also been achieved to give compounds 7-12. Antimicrobial activity of compounds 5a-c against Aspergillus fumigatus, Penicillium italicum, Syncephalastrum racemosum, Candida albicans, Staphylococcus aureus, Pseudomonas aeruginosa, Bacillus subtilis, Escherichia coli is described.
Subject(s)
Anti-Bacterial Agents , Heterocyclic Compounds , Triazines , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/pharmacology , Bacteria/drug effects , Glucose/analogs & derivatives , Glucose/chemistry , Heterocyclic Compounds/chemical synthesis , Heterocyclic Compounds/pharmacology , Microbial Sensitivity Tests , Molecular Structure , Structure-Activity Relationship , Triazines/chemical synthesis , Triazines/pharmacologyABSTRACT
Synthetic routes towards different 2-alpha-L-arabinopyranosyl-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-/ones or thiones were investigated. Primary human anticancer screening of two selected compounds resulted in an active compound against SF-268 (CNS) cell line.
Subject(s)
Antineoplastic Agents/chemical synthesis , Triazines/chemical synthesis , Antineoplastic Agents/therapeutic use , Cell Line, Tumor , Drug Screening Assays, Antitumor , Humans , Molecular Structure , Triazines/therapeutic useABSTRACT
The 1-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-3-aryl-5-benzyl (or substituted benzyl)-1,2,4-triazin-6(1H)-/ones or thiones were prepared via galactosidation of 3-aryl-5-benzyl (or substituted benzyl)-1,2,4-triazin-6(1H)-/ones or thiones with 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide. The structure of the new galactosyl derivatives was based on both spectroscopic and chemical evidences.
Subject(s)
Antineoplastic Agents/chemical synthesis , Galactosides/chemistry , Triazines/chemical synthesis , Molecular StructureABSTRACT
Selective synthesis and reactions of different 6-substituted-2-beta-D-galactosyl-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-ones using the developed amino or aryl protecting group strategy were investigated. Primary human anticancer screening of twelve selected compounds (in vitro) resulted in an active compound against both MCF7 (Breast) and SF-268(CNS) cell lines.
