Microwave assisted synthesis of naphthopyrans catalysed by silica supported fluoroboric acid as a new class of non purine xanthine oxidase inhibitors |
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| Institution: | 1. Department of Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar 143005, Punjab, India;2. Department of Pharmaceutical Chemistry, ISF College of Pharmacy, Moga, Punjab, India;3. Sri Sai College of Pharmacy, Badhani, Pathankot 145001, Punjab, India;1. Laboratory for Drug Design and Synthesis, Centre for Chemical and Pharmaceutical Sciences, School of Basic and Applied Sciences, Central University of Punjab, Bathinda 151 001, India;2. Centre for Biosciences, School of Basic and Applied Sciences, Central University of Punjab, Bathinda 151 001, India;3. Centre for Genetic Diseases and Molecular Medicine, Central University of Punjab, Bathinda 151 001, India;1. College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, PR China;2. School of Science and Technology, Zhejiang International Studies University, Hangzhou, Zhejiang 310012, PR China;1. Graduate School of Human Life Science, Osaka City University, Osaka 558-8585, Japan;2. Graduate School of Integrated Arts and Sciences, University of Tokushima, Tokushima 770-8502, Japan;3. Faculty of Human Life Science, Shikoku University, Tokushima 770-1192, Japan;1. Tercan Vocational High School, Erzincan Binali Yildirim University, Erzincan 24800, Turkey;2. Deparment of Chemistry, Faculty of Science, Ataturk University, Erzurum 25240, Turkey;3. Department of Chemistry, Faculty of Science and Arts, ?nönü University, Malatya 44280, Turkey;4. Bioinformatics and Genetics Department, Faculty of Engineering and Natural Sciences, Kadir Has University, Istanbul 34083, Turkey;5. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Mersin University, Mersin 33169, Turkey;1. Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China;2. Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang 110016, China;3. School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, China;1. Key Laboratory of Structure-based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China;2. Department of Geratology, The First Affiliated Hospital, China Medical University, Shenyang 110001, China;3. Division of Hematology/Oncology, Department of Medicine, Beth Israel Deaconess Medical Center and Harvard Medical School, Boston, MA 02215, USA |
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| Abstract: | A series of naphthopyrans was synthesized employing silica supported fluoroboric acid under solvent free conditions in a microwave reactor. The catalytic influence of HBF4–SiO2 was investigated in detail to optimize the reaction conditions. The synthesised compounds were evaluated for in vitro xanthine oxidase inhibitory activity for the first time. Structure–activity relationship analyses have also been presented. Among the synthesised compounds, NP-17, NP-19, NP-20, NP-23, NP-24, NP-25 and NP-26 were the active inhibitors with an IC50 ranging from 4 to 17 μM. Compound NP-19 with a thiophenyl ring at position 1 emerged as the most potent xanthine oxidase inhibitor (IC50 = 4 μM) in comparison to allopurinol (IC50 = 11.10 μM) and febuxostat (IC50 = 0.025 μM). The basis of significant inhibition of xanthine oxidase by NP-19 was rationalized by its molecular docking at MTE binding site of xanthine oxidase. |
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| Keywords: | Xanthine oxidase Naphthopyrans Fluoroboric acid Silica Microwave |
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