SYNTHESIS, CHARACTERIZATION AND ANTI-INFLAMMATORY EVALUATION OF SOME NEW 2-(3-FLUOROBIPHENYL-4-YL) PROPANOIC ACID DERIVATIVESAbstract
Different new compounds derived from 2-(3-flourobiphenyl-4-yl) propanohydrazide  as starting material were synthesized. Reaction  with maleic anhydride, succinic anhydride and phthalic anhydride gave the corresponding cyclicimides [3a-c]. The hydrazone derivatives [4a-d] were obtained by condensation of compound  with 2,4-dimethoxybenzaldehyde, 4-(N,N-dimethylamino)benzaldehyde, 3-hydroxybenzaldehyde and 2-hydroxybenzaldehyde. The cyclization of  with CS2 in presence potassium hydroxide and hydrazine hydrate gave 1,2,4-triazole compound , that condensation either with 2,4-dimethoxybenzaldehyde, 4-(N,N-dimethyl amino) benzaldehyde, 3-hydroxybenzaldehyde and 2-hydroxybenzaldehyde to give the corresponding Schiff-bases [6a-d]. The cyclization of hydrazone derivatives [4a-d] with phenyl isocyanate, maleic anhydride, succinic anhydride and phthalic anhydride gave the corresponding aza-β-lactams [7a-d], oxazepine [8,9,10 a-d]. The structures of new compounds are supported by FT-IR, 1H-NMR and 13C-NMR. Compounds [3c], [4c], [8d], [7d] and [4b] were evaluated in vivo for their anti-inflammatory activity comparable to the standard drug flurbiprofen. Compound 2-(2-hydroxyphenyl)-3-[2-(3-fluorobiphenyl-4-yl)] propan- amido-2,3-dihydro-1,3-oxazepine-4,7-dione [8d] showed anti-inflammatory activity more than the standard drug flurbiprofen, in the egg-albumin induced paw edema in rats.
Ahmed W. Naser *, Ahmed J. Al-Musawi, Ammar A. Fadhil and Nada N. Al-Shawi
Department of Chemistry, College of Science, University of Baghdad, Baghdad, Iraq
30 September, 2016
21 November, 2016
01 December, 2016
01 April, 2017