Synthesis, anti-inflammatory, bactericidal activities and docking studies of novel 1,2,3-triazoles derived from ibuprofen using click chemistry
| Autor: | Kishore Kumar Angajala, Sunitha Vianala, M. Raghavender, Murali Krishna Thupurani, Ramesh Macha, P. J. Pathi |
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| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
Drug
medicine.drug_class media_common.quotation_subject Triazole Ibuprofen 010402 general chemistry 01 natural sciences Anti-inflammatory Docking chemistry.chemical_compound In vivo medicine media_common Multidisciplinary biology 010405 organic chemistry Chemistry Click chemistry Research Active site Triazoles Combinatorial chemistry 0104 chemical sciences Docking (molecular) biology.protein Bactericidal medicine.drug |
| Zdroj: | SpringerPlus |
| ISSN: | 2193-1801 |
| Popis: | Background Nonsteroidal anti-inflammatory drugs are of vast therapeutic benefit in the treatment of different types of inflammatory conditions. 1,2,3-Triazoles and their derivatives have a wide range of applications as anti-bacterial, anti-fungal, anti-tubercular, cytostatic, anti-HIV, anti-allergic, anti-neoplastic and anti-inflammatory (AI) agents. Considering the individual biological and medicinal importance of ibuprofen and 1,2,3-triazoles, we wanted to explore novel chemical entities based on ibuprofen and triazole moieties towards their biological significance. Results Click chemistry has utilized as an ideal strategy to prepare novel ibuprofen-based 1,4-disubstituted 1,2,3-triazole containing molecules. These compounds were screened for their in vivo AI activity, among all the synthesized analogues 13o was shown potent effect than the reference AI drug ibuprofen at the same concentration (10 mg/kg body weight). Compounds 13l, 13g, 13c, 13k, 13i, 13n, 13m and 13j were shown significant AI activity. These triazole analogues were also screened for their bactericidal profile. Compounds 13c, 13i, 13l and 13o exhibited considerable bactericidal activity against gram positive and gram negative strains. In addition to this, molecular docking studies were also carried out into cyclooxygenase-2 active site to predict the affinity and orientation of these novel compounds (13a–q). Conclusions In summary, we have designed and synthesized 1,2,3-triazole analogues of ibuprofen in good yields using Click chemistry approach. AI and bactericidal activities of these compounds were evaluated and shown remarkable results. Electronic supplementary material The online version of this article (doi:10.1186/s40064-016-2052-5) contains supplementary material, which is available to authorized users. |
| Databáze: | OpenAIRE |
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