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Bioorg Med Chem Lett ; 25(17): 3671-5, 2015 Sep 01.
Article in English | MEDLINE | ID: mdl-26152425

ABSTRACT

In the present study a series of O-substituted pyrazoles 7(a-f) and N-substituted pyrazoles 9(a-f) were synthesized via phase-transfer catalyzed reaction of ethyl 5-(bromomethyl)-1,3-diphenyl-1H-pyrazole-4-carboxylate 5 with various oxygen and nitrogen containing compounds in presence of tetrabutylammonium bromide (TBAB) in THF. The compound 5 was obtained by the efficient bromination with N-bromosuccinimide (NBS) in presence of a catalytic amount of azoiso-bis-butyro nitrile (AIBN) in refluxing CCl4. The synthesized compounds were evaluated for their in vitro antimicrobial and antidiabetic activity and were compared with standard drugs. Among the synthesized compounds, compound 9b emerged as an excellent antimicrobial and antidiabetic agent. Newly synthesized compounds were characterized by analytical and spectral (IR, (1)H NMR, (13)C NMR and LC-MS) methods.


Subject(s)
Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Hypoglycemic Agents/chemistry , Hypoglycemic Agents/pharmacology , Pyrazoles/chemistry , Anti-Infective Agents/chemical synthesis , Catalysis , Chemistry Techniques, Synthetic , Drug Evaluation, Preclinical/methods , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/pharmacology , Glycoside Hydrolase Inhibitors/chemistry , Glycoside Hydrolase Inhibitors/pharmacology , Hypoglycemic Agents/chemical synthesis , Inhibitory Concentration 50 , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Molecular Docking Simulation , Structure-Activity Relationship , alpha-Amylases/antagonists & inhibitors , alpha-Amylases/chemistry , alpha-Amylases/metabolism , alpha-Glucosidases/metabolism
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