Synthesis and biological evaluation of novel 2‐(4‐O‐β‐D‐glucosidoxyphenyl)‐4,5‐disubstituted imidazoles

Abstract

in Wiley InterScience (www.interscience.wiley.com).A series of 2-(4-hydroxyphenyl)-4,5-disubstituted imidazoles (1a-e) prepared from a-diketones, ammonium acetate, and p-hydroxybenzaldehyde, which were glucosylated by using a-acetobromoglucose to form 2-(4-O-b-D-2,3,4,6-tetra-O-acetyl-glucosidoxyphenyl)-4,5-disubstituted imidazoles (2a-e) which on catalytic deacetylation with CH 3 ONa in methanol afforded the title compound 2-(4-O-b-D-glucosidoxyphenyl)-4,5-disubstituted imidazoles (3a-e). Compounds were characterized by elemental analysis and by instrumental technique, similarly the title compounds were investigated for antimicrobial and antifungal activity.

Synthesis, spectroscopic characterization and pharmacological evaluation of oxazolone derivatives

“…Oxazolone plays a very vital role in the manufacture of various biologically active drugs, such as analgesic, anti-inflammatory, antidepressant, anticancer, antimicrobial, antidiabetic and anti-obesity compounds. 18,19 In the literature, the syntheses of oxazolone derivatives were achieved by condensation of aldehydes with N-benzoyl/N-acetyl glycine in the presence of various reagents and catalysts, such as, ZnCl 2 , 20 KF/NaOAc, 21 Al 2 O 3 -H 3 BO 3 , 22 Bi(III) salts 23 and Pb(OAc) 2 . 24 Herein, the synthesis of a series of 4-(arylmethylidene)-2-phenyl/methyl-5(4H)-oxazolone derivatives (2-7) using a literature method 25 by the condensation of an aldehyde with N-benzoyl/N-acetyl glycine in the presence of zinc oxide as a catalyst at room temperature in ethanol is reported.…”

Design, Synthesis, and Evaluation of the Anticancer Properties of a Novel Series of Imidazolone Fused Pyrazolo[1,5‐a]pyrimidine Derivatives

“…The hippuric acid derivatives 6a–e was obtained by the treatment of the corresponding acid chlorides 5a–e with glycine in the presence of an aqueous sodium hydroxide solution at room temperature . The hippuric acid derivatives 6a–e were subsequently treated with a variety of different substituted aldehydes in the presence of acetic anhydride and sodium acetate at 80°C, in accordance with the previously reported Erlenmeyer–Plochl reaction, to give the corresponding oxazolones 7a–t .…”

“…Imidazolone derivatives are usually prepared from the corresponding oxazolones . Oxazolones themselves have been used as important synthons for the synthesis of several organic molecules, including amino acids, dyes, and drugs , as well as many biologically active drug compounds, including analgesic, anti‐inflammatory, anti‐depressant, anticancer, anti‐microbial, anti‐diabetic, and anti‐obesity agents . The chemistry of 5‐(4)‐oxazolones has been reviewed in detail by Carter .…”

Efficient Microwave-Assisted Synthesis of N-(2-Alkyl/aryl-4-phenyl-1H-imidazol-1-yl)-2-phenylacetamides

“…[12][13][14][15] However, there are only a few protocols found in literature for the synthesis of N-(2-alkyl=aryl-4-phenyl-1H-imidazol-1-yl)-2-phenylacetamides. These protocols require catalyst and hard purification methods.…”