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Design and synthesis of novel heterocyclic derivatives as soluble epoxide hydrolase inhibitors

عنوان مقاله: Design and synthesis of novel heterocyclic derivatives as soluble epoxide hydrolase inhibitors
شناسه ملی مقاله: ISOC27_399
منتشر شده در بیست و هفتمین کنفرانس شیمی آلی ایران در سال 1398
مشخصات نویسندگان مقاله:

Sara Mehrandish - Student Research Committee, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran
Ana Sedaghat - Department of Pharmaceutical Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran
Elham Rezaee Zavareh - Department of Pharmaceutical Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran
Sayyed Abbas Tabatabai - Department of Pharmaceutical Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran

خلاصه مقاله:
Soluble epoxide hydrolase (sEH), is an enzyme belongs to serine hydrolase family. sEH inhibition provides a novel approach to treat common ailments such as hypertension and inflammation. We designed and synthesized novel inhibitors, having tetrazole core to improve pharmacokinetic profile and potency.1 In this study, 5-phenyl-5H-tetrazole (1) was prepared by the reaction of benzonitrile and sodium azide using freshly synthesized ZnBr2 as the catalyst.2 Then N-benzylation of the compound 1 with 4-nitrobenzylbromide leads to crystalline compound 2.3 Then the compound 3 is resulted by reduction of nitro group of compound 2 with a mixture of iron powder, glacial acetic acid, ethanol and water under sonication for one hour.4 The final products (4) were afforded by treating of 4-((5-phenyl-2H-tetrazol-2-yl)methyl)aniline (3) with different benzoyl chlorides at room temperature in dry tetrahydrofuran (Fig. 1).3Finally, some novel compounds bearing a tetrazole ring were designed. The designed compounds showed high affinity to the active site of the sEH enzyme and were synthesized in good yield and were characterized by IR, Mass, HNMR, and CNMR.

کلمات کلیدی:
Soluble epoxide hydrolase, Tetrazole, Synthesis

صفحه اختصاصی مقاله و دریافت فایل کامل: https://civilica.com/doc/1164177/