Synthesis, biological evaluation of benzothiazole derivatives bearing a 1,3,4-oxadiazole moiety as potential anti-oxidant and anti-inflammatory agents.

Twenty benzothiazole derivatives bearing a 1,3,4-oxadiazole moiety were synthesized and evaluated for their anti-oxidant and anti-inflammatory activities. Among these compounds, 8h and 8l were appeared to have high radical scavenging efficacies as 0.05 ± 0.02 and 0.07 ± 0.03 mmol/L of IC50 values in ABTS+ bioassay, respectively. In anti-inflammatory tests, compound 8h displayed good activity with 57.35% inhibition after intraperitoneal administration, which was more potent than the reference drug (indomethacin). Molecular modeling studies were performed to investigate the binding mode of the representative compound 8h into COX-2 enzyme. In vitro enzyme study implied that compound 8h exerted its anti-inflammatory activity through COX-2 inhibition.

Synthesis of 2-alkynyl substituted 4'-thioadenosine derivatives and their binding affinities at the adenosine receptors.

On the basis of high binding affinity of 2-hexynyl-N(6)-methyladenosine and N(6)-substituted-4'-thioadenosine derivatives at the A3 adenosine receptor (AR), novel 2-alkynyl-substituted-N(6)-methyl-4'-thioadenosine derivatives, combining the characteristics of two classes of nucleosides were designed and synthesized from D-gulonic gamma-lactone via palladium-catalyzed cross coupling reaction as a key step. Among compounds tested, only compound 3b showed moderate binding affinity at the human A3 adenosine receptor without binding affinities at other subtypes.

Synthesis of 2-(3'-azido- and 3'-amino-3'-deoxy-beta-D-ribofuranosyl)thiazole-4-carboxamide.

In view of biological activities of tiazofurin and azido or aminosugar nucleosides, novel azido- and amino-substituted tiazofurin derivatives (1 and 2) were efficiently synthesized starting from 1,2;5,6-di-O-isopropylidene-D-glucose.