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

• Published in: Monatshefte für Chemie Vol. 153; no. 12; pp. 1225 - 1234
• Main Authors: Yilmaz, Özgür, Özdemir, Sadin, Gonca, Serpil, Simsek Kus, Nermin, Kaynarpınar, Hatice Derya
• Format: Journal Article
• Language: English
• Published: Vienna Springer Vienna 01.12.2022; Springer Nature; Springer Nature B.V
• Subjects: Acetylene; Analytical Chemistry; Antiinfectives and antibacterials; Biological activity; Chemical synthesis; Chemistry; Chemistry and Materials Science; Chemistry, Multidisciplinary; Chemistry/Food Science; E coli; Fragmentation; Inorganic Chemistry; Lithium aluminum hydrides; Microorganisms; NMR; Nuclear magnetic resonance; Organic Chemistry; Original Paper; Physical Chemistry; Physical Sciences; Potassium permanganate; Pseudomonas aeruginosa; Ribose; Science & Technology; Theoretical and Computational Chemistry; Antimicrobial; DNA cleavage; Microbial cell viability inhibition; Antioxidant; Ribose; NUCLEOSIDE; ANALOGS; LIVER; INDUCTION
• ISSN: 0026-9247; 1434-4475
• DOI: 10.1007/s00706-022-02989-7

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; KMnO 4 /CuSO 4 ·5H 2 O and OsO 4 /NaIO 4 /2,6-lutidine. Ester groups of dimethyl 2-formylfuran-3,4-dicarboxylate were reduced by LiAlH 4 and NaBH 4 . 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-dihydroxytetrahydrofuran-2,5-dicarboxylate. The structures of the synthesized molecules were determined from 1 H 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/dm 3 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 . Graphical abstract