New pyrimidine-N-β-D-glucosides: synthesis, biological evaluation, and molecular docking investigations

In this study, syntheses of new pyrimidine-coupled N-beta-glucosides and tetra-O-acetyl derivatives were carried out. All glycoconjugates were investigated in comparison with known chemotherapeutic agents in terms of their antimicrobial and anticancer functions and DNA/protein binding affinities. Spectral data showed that all glycoside derivatives were obtained by diastereoselectivity as beta-anomers. Both tested groups exhibited strong antiproliferative activity (2.29-66.84 mu g/mL), but some of them had sufficiently ideal % cytotoxicity values (10.01%-16.78%). And also all synthetic compounds exhibited remarkable antibacterial activity against human pathogenic bacteria. Binding of these compounds to CT-DNA resulted in significant changes in spectral properties, consistent with groove binding. Molecular docking studies of some compounds revealed that the docking score, complex energy, and MM-GBSA Delta GBind energy values were consistent with the experimental results, which showed that the new compounds were potent chemotherapeutic agents. Overall bioactivity results suggest that these compounds may be candidates as new chemotherapeutic agents and deserve further pharmacological evaluation

Chemical composition and biological activity of essential oils of sempervivum brevipilum muirhead

This work was supported by grants from Karadeniz Technical University Research Fund.The essential oils of the fresh flower, leaf, and stem of Sempervivum brevipilum Muirhead. (Crassulaceae) were isolated by hydrodistillation in a modified Clevenger-type apparatus, and characterized by GC-FID and GC-MS. A total of fifty, fourty-three, and thirty-one compounds were identified, constituting over 92.6%, 92.6%, and 94.3% of oil composition of the flower, leaf, and stem of S. brevipilum, respectively. The chemical profile reveals the dominance of hydrocarbons (flower: 65.3%, leaf: 47.6%, stem: 71.1%). The major compounds of essential oils from S. brevipilum were tetracosane (20.2%) in flower, 1,2-diphenyl ethandione (16.1%) in leaf and docosane (30.5%) in stem. Monoterpene hydrocarbons were the major class of terpenoids in flower (2.2%) and in stem (1.8%), oxygenated diterpene was the major class of terpenoids in leaf (4.5%). Oxygenated monoterpenes were in minor amounts in all parts (flower: 0.3%, leaf: 0.7%, stem: 0.1%) of the plant. In addition, antimicrobial activities of the essential oils of S. brewpilum were investigated. The oils didn't show any antibacterial and antifungal activity against tested bacteria, but showed high antituberculostatic activity against Mycobacterium smegmatis

Diastereoselective synthesis, characterization, investigation of anticancer, antibacterial activities, in silico approaches and DNA/BSA binding affinities of novel pyrimidine-sugar derivatives

Eighteen novel carbohydrate conjugates (1-9) and their tetra-O-acetyl derivatives (10-18) were synthesized in total and evaluated for their biological properties, including antimicrobial and anticancer functions, and DNA/protein binding affinities. The compounds were prepared by firstly glycosylation and secondly acetylation methods. The structures of all compounds were elucidated by spectral analysis and the results showed that the glycoconjugates were obtained by diastereoselectivity as pure β- anomer. To observe cell proliferation, cytotoxicity and microdilution, different cancer cell lines (Hep3B, A549, HeLa, C6, HT29, MCF7) were treated with pyrimidine N-β-D-glycosides (1-9) and their tetra-O-acetyl derivatives (10-18). These new carbohydrate conjugates and the controls showed the same non-toxic property to the cells, while 10-18 displayed lower cytotoxic potency than 1-9. And to support the experimental results of some compounds (8, 9, 17, and 18) whose pharmacological properties were determined, molecular docking studies were performed, which belonged to the in silico methods. The values of the binding parameters of these compounds with different receptors were determined by molecular docking. Studies on pathogenic bacteria revealed that both groups of new compounds exhibited significant antimicrobial activity with low concentrations (31.25-125 µg/mL). Significant data have been obtained indicating that they can bind to DNA via groove binding, with binding constants ranging from 1.1 × 103 to 4.0 × 104. In summary, preliminary information indicates that acetylated derivatives (10-18) have effective pharmacological properties

Molecular docking, synthesis and biological evaluation (enzyme inhibition, antimicrobial and antioxidant) of methoxy benzoin/benzil/stilbenoid derivatives

In this study. methoxy benzoin compounds (1-10) were synthesized from the corresponding aromatic aldehydes based on a screening of biological activity. Oxidation and reduction of benzoins (1-10) yielded the corresponding benzils (11-20) and stilbenoids (21-29), respectively. The enzyme inhibition, antimicrobial, and antioxidant activities of 1-29 were evaluated. 1, 14, 19, and 28 against alpha-amylase, 15 and 19 against a-glucosidase, 2, 4, 14, 18, 25 and 26 against tyrosinase, 2, 7, and 23 against AChE, and 7, and 13 against BChE showed similar activity to the standard used. Among the methoxy benzoin derivatives, 4 proved to be the most active compound against E.coli, Y.pseudotuberculosis, M. smegmatis, and C.albicans in the range of 41-82 mu g/mL MIC values. All benzil derivatives displayed bioactivity against M.smegmatis and C. albicans. Compounds 18 and 11 were found to be most effective against M.smegmatis, and compounds 11 and 17 were found to be the most effective against C.albicans. All stilbenoid type compounds showed selective activity against B.cereus. Compounds 21 and 22 were the most effective stilbenoid compounds against M. smegmatis. Benzoins (1-10) were the most effective antioxidants among all three groups compared to the tested methods, which can be attributed to the free hydroxyl at the benzylic position. As a result, the change of carbon skeleton and substitution at different positions of synthesized organic compounds also caused the variation of biological activity