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

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Abstract

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[3.2.1.02,4]oct-6-ene-6,7-dicarboxylate was synthesized in high yield. Fragmentation reaction of dimethyl 3,8-dioxatricyclo[3.2.1.02,4]oct-6-ene-6,7-dicarboxylate gave dimethyl 3,4-dihydroxytetrahydrofuran-2,5-dicarboxylate. The structures of the synthesized molecules were determined from 1H NMR, 13C 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/dm3, respectively. It displayed 100% microbial cell viability inhibition against Escherichia coli at 250 mg/dm3.

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Acknowledgements

The authors are indebted to Mersin University [BAP-FBE KB (ÖY) 2014-1 DR and 2017-1-TP2-2175] for their financial support to this work.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Arts and Sciences, Mersin University, Yenisehir, TR-33343, Mersin, Turkey

    Özgür Yilmaz, Nermin Simsek Kus & Hatice Derya Kaynarpınar

  2. Food Processing Program, Technical Science Vocational School, Yenisehir, TR-33343, Mersin, Turkey

    Sadin Özdemir

  3. Department of Pharmaceutical Microbiology, Faculty of Pharmacy, Mersin University, Yenisehir, TR-33343, Mersin, Turkey

    Serpil Gonca

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  1. Özgür Yilmaz
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  2. Sadin Özdemir
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  5. Hatice Derya Kaynarpınar
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Correspondence to Nermin Simsek Kus.

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Yilmaz, Ö., Özdemir, S., Gonca, S. et al. A novel approach to the synthesis of substituted ribose and furan derivatives: biological activity of dimethyl 3,4-dihydroxytetrahydrofuran-2,5-dicarboxylate. Monatsh Chem 153, 1225–1234 (2022). https://doi.org/10.1007/s00706-022-02989-7

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