title: Novel 5-functionalized-pyrazoles: Synthesis, characterization and pharmacological screening.
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.
authors.affiliation: Department of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India.
authors.forename: Shridevi D
authors.initials: SD
authors.lastname: Doddaramappa
authors.affiliation: Department of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India. Electronic address: shridevi20@gmail.com.
authors.forename: K M
authors.initials: KM
authors.lastname: Lokanatha Rai
authors.affiliation: Department of Chemistry, Vidyavardhaka College of Engineering, Gokulam, Mysore 570 002, India.
authors.forename: Ningaiah
authors.initials: N
authors.lastname: Srikantamurthy
authors.affiliation: Department of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India.
authors.lastname: Chandra
authors.affiliation: Department of Studies in Biotechnology, Manasagangotri, University of Mysore, Mysore 570 006, India.
authors.forename: Javarasetty
authors.initials: J
authors.lastname: Chethan
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D004353:Drug Evaluation, Preclinical / Q000379:methods; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology; D065089:Glycoside Hydrolase Inhibitors / Q000737:chemistry / Q000494:pharmacology; D007004:Hypoglycemic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D062105:Molecular Docking Simulation; D011720:Pyrazoles / Q000737:chemistry*; D013329:Structure-Activity Relationship; D000516:alpha-Amylases / Q000037:antagonists & inhibitors / Q000737:chemistry / Q000378:metabolism; D000520:alpha-Glucosidases / Q000378:metabolism
chemical_list: D000890:Anti-Infective Agents; D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D007004:Hypoglycemic Agents; D011720:Pyrazoles; C031280:pyrazole; D000516:alpha-Amylases; D000520:alpha-Glucosidases
keywords: N-substitution; NBS; O-substitution; Phase transfer catalysis; Pyrazole-4-carboxylate; TBAB