Abstract
A series of novel N-glycoside phenyl pyrazole derivatives 5-9 were synthesized by initial reactions of Acetophenone semicarbazone with phosphorus oxychloride to give 3-phenyl-1H-pyrazole-4-carbaldehyde 2 which was reacted with glucose to give N-glycoside. Some of the synthesized compounds have been screened as antibacterial and antifungal. The structures of the synthesized compounds have been deduced from their elemental analysis and spectral (IR, 1 H-NMR) data.
Highlights
Pyrazole derivatives were established as important biologically active heterocyclic compounds. These derivatives have been the subject of many research studies due to their wide spread potential activities such as anti-inflammatory [1], antipyretic [2], antimicrobial,[3] antiviral [4], antitumor [5], anticonvulsant [6], antidepressant [7], a number of nucleoside analogues have been found to show a broad spectrum of biological activity and have stimulated considerable interest as potential antitumor and antiviral agents [8]
KOH (1mmol) was added a solution of acetobromoglucose (1mmol, 0.410g) in acetone 20 ml, the reaction mixture was stirred at room temperature for 8 hours
Acetophenone semicarbazone 1 was reacted with two moles of phosphorus oxychloride in the presence of DMF to give 3-phenyl-1H-pyrazole-4-carbaldehyde 2 in 58% yields
Summary
Pyrazole derivatives were established as important biologically active heterocyclic compounds. 1H NMR spectra was obtained on a Brucker AC 200F instrumental at r.t in the solvent indicated chemical shifts are reported in ppm from TMS as the internal standard. 1H NMR spectra was measured on a Varian spectrophotometer at 300 MHz using DMSO-d6 or CDCl3 as solvent at chemistry department faculty of science, Bardouex University – France. The compound (1) (0.05 mol) was added drop wise with stirring to a mixture of POCl3- DMF The latter was prepared by the slow addition of POCl3 (0.11 mol, 10 ml) to DMF (0.22 mol) below 5 ̊C. Found: C, 69.83; H, 4.68; N, 16.30
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