Synthesis and evaluation of pharmacological activities of some 3-O-benzyl-4-C-(hydroxymethyl)-1,2-O-isopropylidene-α-D-ribofuranose derivatives as potential anti-inflammatory agents and analgesics

• Published in: Research in pharmaceutical sciences Vol. 15; no. 3; pp. 209 - 217
• Main Authors: Rahman, Fahad Imtiaz, Hussain, Fahad, Saqueeb, Nazmus, Abdur Rahman, S M
• Format: Journal Article
• Language: English
• Published: Iran Wolters Kluwer - Medknow 01.06.2020; Wolters Kluwer Medknow Publications
• Subjects: Original; α-d-ribofuranose; anti-inflammatory; anti-nociception; cytotoxicity; modified derivatives; Modified derivatives; Cytotoxicity; Anti-nociception; Anti-inflammatory; α-D-ribofuranose
• ISSN: 1735-5362; 1735-9414
• DOI: 10.4103/1735-5362.288423

α-D-ribofuranose analogues are reported to have multifarious biological properties such as analgesic, anti-inflammatory, and antiviral activities. The present study aims to synthesize some α-D- ribofuranose derivatives and investigate their biological properties. Four derivatives ( , , , and ) were synthesized from the starting material 3-O- benzyl-4-C-(hydroxymethyl)-1,2-O-isopropylidene-α-D-ribofuranose subsequent benzylation, tosylation, and acetylation reactions in good yields. The compounds were confirmed by spectroscopic methods such as Fourier-transform infrared (FTIR) and proton nuclear magnetic resonance ( HNMR), and then evaluated for various pharmacological activities using standard and procedures. Compound (50 mg/kg) exhibited both central and peripheral analgesic activity in the tail immersion test (2.52 ± 0.14 min tail flicking reaction time after 30 min from administration, < 0.001) and the acetic acid-induced writhing test (65.33 ± 2.06% reduction in abdominal writhing, < 0.001) respectively. In the anti-inflammatory assay, percent paw edema inhibition of carrageenan-induced rats for compounds and (100 mg/kg) after 4 h of administration were 82.6% ( < 0.001) and 87.6% ( < 0.001), respectively. The compounds were also tested for antioxidant activity in 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay, antimicrobial property in disk diffusion assay, and cytotoxicity in HeLa cell line; however, no significant results were observed in any of those tests. Our study indicated that some of the synthesized compounds exhibited promising analgesic and anti-inflammatory effects and may serve as potential lead compounds.