Rahman Fahad Imtiaz, Hussain Fahad, Saqueeb Nazmus, Abdur Rahman S M
Department of Clinical Pharmacy and Pharmacology, Faculty of Pharmacy, University of Dhaka, Dhaka, Bangladesh.
Res Pharm Sci. 2020 Jul 3;15(3):209-217. doi: 10.4103/1735-5362.288423. eCollection 2020 Jun.
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.
FINDINGS / RESULTS: 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.
据报道，α-D-呋喃核糖类似物具有多种生物学特性，如镇痛、抗炎和抗病毒活性。本研究旨在合成一些α-D-呋喃核糖衍生物并研究其生物学特性。
以3-O-苄基-4-C-(羟甲基)-1,2-O-异丙叉基-α-D-呋喃核糖为起始原料，经后续的苄基化、甲苯磺酰化和乙酰化反应，以良好的产率合成了四种衍生物（、、和）。通过傅里叶变换红外光谱（FTIR）和质子核磁共振（HNMR）等光谱方法对化合物进行了确认，然后使用标准和程序对其各种药理活性进行了评估。
化合物（50 mg/kg）在尾部浸入试验（给药30分钟后甩尾反应时间为2.52±0.14分钟，<0.001）和醋酸诱导的扭体试验（腹部扭体减少65.33±2.06%，<0.001）中分别表现出中枢和外周镇痛活性。在抗炎试验中，化合物和（100 mg/kg）给药4小时后对角叉菜胶诱导的大鼠足爪水肿的抑制率分别为82.6%（<0.001）和87.6%（<0.001）。还对化合物进行了2,2-二苯基-1-苦基肼（DPPH）自由基清除试验中的抗氧化活性、纸片扩散试验中的抗菌性能以及HeLa细胞系中的细胞毒性测试；然而，在任何这些测试中均未观察到显著结果。
我们的研究表明，一些合成化合物表现出有前景的镇痛和抗炎作用，可能作为潜在的先导化合物。
