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Synthesis Sulfide And Carbonyl Substituted Imidazopyridine Derivatives

Posted on:2017-11-30Degree:MasterType:Thesis
Country:ChinaCandidate:Z G BianFull Text:PDF
GTID:2404330566972551Subject:Medicinal chemistry
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The thesis is divided into two parts,the first part includes the reaction of imidazopyridine compound with sulfuryl chloride,thiophenol compound,and ammonium iodide is used as an inducer,via C-H functionalization process,direct synthesis of C-S bond structure is obtained,then we synthesize a series of compounds.Compound structures are confirmed by NMR,HRMS,FTIR and other methods,all structures are proved.The second part includes a series of compounds similar to the anti-gout drugs benzbromarone based on bioisostere principle,many similar compounds are synthesized and we hope that these compounds have some anti-gout effect and will lay the foundation for future bioscreening.(2)Ammonium iodide induced synthesis of imidazopyridine derivativesAmmonium iodide compound is environmentally friendly,compared to metal palladium,copper,iron salt and other metal catalysts,which can pollute the environment.Imidazole compounds normally have many biological activities,some important drugs contain an imidazole structure,and imidazole structure is an important pharmacophore.Construction of C-S bond has always been a research hot in organic chemistry research community.Several synthetic methods of constructing C-S bond has been reported until now,different catalysts have been used,such as other metal catalysts,a palladium catalyst,a copper catalyst,an iron catalyst,but there are some limitations to these methods,and most methods are not green catalysts.In this thesis,imidazopyridine compound was reacted with benzenesulfonyl chloride and thiophenol,ammonium iodide was used as an inducer.a series of compounds were synthesized with potential biological activities.(2)Compounds similar to the anti-gout drugs benzbromarone based on bioisostere principleWith the social development and people’s living standards improvement,some changes in people’s eating habits,environmental pollution and other factors,these factors lead to the incidence of gout increase annually.Human uric acid increased,and this leads to the formation of urate crystals in the joints urate crystals precipitate formed gout.Gout may also cause high blood pressure,cardiovascular disease,chronic kidney disease and other complications.So to reduce the body’s uric acid,and we found new compounds to reduce uric acid and to slow down the suffering of patients.Benzbromarone is a good common drug that suppress the body’s production of uric acid and it is a commonly used in clinical URAT1 inhibitor,but it also has obvious side effects.By studying the chemical structure benzbromarone drug research activity center and benzbromarone compound nucleus structure unchanged,we synthesized a series of similar compounds.We hope that the discovery of new compounds can inhibit uric acid better and less side effects of the compound.We hope to find further suppression of uric acid drugs and help for further research to reduce uric acid.All synthesized compounds have structures confirmed by 1H-NMR and 13C-NMR.
Keywords/Search Tags:Gout, Benzbromarone, URAT1 inhibitor, Imidazopyridine:Ammonium iodide
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