A novel approach to the synthesis of substituted ribose and furan derivatives: biological activity of dimethyl 3,4-dihydroxytetrahydrofuran-2,5-dicarboxylate

摘要

In this article, the synthesis of ribose and furan derivatives, which have a high probability of showing biological activity, was performed and their biological activities were discussed. For this purpose, dimethyl 7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate was prepared by the addition reaction of furan to dimethyl acetylene dicarboxylate. Fragmentation reaction of dimethyl 7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate was examined by two different methods; KMnO4/ CuSO4·5H2O and OsO4/NaIO4/2,6-lutidine. Ester groups of dimethyl 2-formylfuran-3,4-dicarboxylate were reduced by LiAlH4 and NaBH4. Dimethyl 7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate was reacted with MCPBA (meta-chloroperbenzoic acid) and dimethyl 3,8-dioxatricyclo[3.2.1.0~(2,4)]oct-6-ene-6,7-dicarboxylate was synthesized in high yield. Fragmentation reaction of dimethyl 3,8-dioxatricyclo[3.2.1.0~(2,4)]oct-6-ene-6,7-dicarboxylate gave dimethyl 3,4-dihydroxy-tetrahydrofuran-2,5-dicarboxylate. The structures of the synthesized molecules were determined from ~1H NMR, ~(13)C NMR, MS, and IR data. Thus, different ribose and furan derivatives likely to exhibit biological activity were obtained in the study. Since dimethyl 3,4-dihydroxytetrahydrofuran-2,5-dicarboxylate is the most effective among synthesized molecules, the biological activity of dimethyl 3,4-dihydroxytetrahydrofuran-2,5-dicarboxylate is discussed in this article. The newly prepared dimethyl 3,4-dihydroxytetrahydrofuran-2,5-dicarboxylate demonstrated 67.62% DPPH radical inhibition ability at 200 mg/ dm3 and it exhibited good antimicrobial activity against several pathogene microorganisms. It degraded the whole of DNA molecule. In addition to these, dimethyl 3,4-dihydroxytetrahydrofuran-2,5-dicarboxylate inhibited the biofilm formation of Staphylococcus aureus and Pseudomonas aeruginosa as 98.36 and 100% at 250 mg/dm~3, respectively. It displayed 100% microbial cell viability inhibition against Escherichia coli at 250 mg/dm~3.