Synthesis, Characterization, and Anti-Inflammatory Activity of Newer Quinazolinone Analogs

Abstract

A series of 3-[2′-(Substitutedbenzylideneamino)phenyl]-2-methyl-6-substituted quinazolin-4-ones (5–10), 3-[2′-(3″-chloro-2″-oxo-4″-substitutedphenylazetidin-1″-yl)phenyl]-2-methyl-6-substitutedquinazolin-4-ones (11–16), and 3-[2′-(2″-substitutedphenyl-4″-oxo-1″,3″-thiazolidin-3″-yl)phentl]-2-methyl-6-substitutedquinazolin-4-ones (17–22) have been synthesized in the present study. The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, 1H NMR, and mass spectral data. All the newly synthesized compounds were screened for anti-inflammatory and analgesic activities.

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“…On standing for 1 h, solidification occur, the product was filtered off, washed with water and dried. (6)(7)(8)(9)(10)(11)(12)(13)(14): To a solution of the appropriate acetophenones (0.01mol) dissolved in ethanol (20ml), was added different substituted 3-amino-2-phenylquinazolin-4-one derivative (5a-5c) (0.01mol) and pH of the resultant solution was adjusted to 4.0-4.5 using glacial acetic acid. The resulting mixture was refluxed for 2-3 h. The solid thus obtained was filtered and purified by column chromatographic method using n-hexane/ethyl acetate (75:25) as eluents.…”

“…R 1= 4-CH 3, R 2 =3-NO 2 , 14. R 1= 4-CH 3, R 2 = 3-OH Anti-inflammatory Activity: Anti-inflammatory activity of the newly synthesized compounds was determined using carrageenan-induced foot paw edema assay method in rats and indomethacin was used as a standard drug 9 . Unless otherwise stated, the following conditions were employed in all experiments.…”

“…Unless otherwise stated, the following conditions were employed in all experiments. Target compounds (6)(7)(8)(9)(10)(11)(12)(13)(14) were suspended in aqueous solution of carboxymethyl cellulose (CMC, 0.5% w/v) and administered orally at a dose level of 10mg/kg of synthesized compounds (6)(7)(8)(9)(10)(11)(12)(13)(14), respectively. Control animals were similarly treated with aqueous solution of carboxymethyl cellulose (CMC, 0.5% w/v).…”

“…Structures of the ligands 2,3-disubstituted quinazolinone derivatives containing Schiff bases (6)(7)(8)(9)(10)(11)(12)(13)(14) were drawn by using chemdraw ultra 8.0 and the three-dimensional structures of the compounds were constructed using the Maestro interface. All 3D ligands were subjected to energy minimization and optimization using Ligprep module.…”

“…Quinazolin-4(3H)-one represents a versatile lead molecule for the design of potential bioactive agents [1][2][3][4][5][6][7] and the pharmaceuticals containing quinazolinone nucleus show varied biological activities as different substitution patterns results in diverse biological properties [8][9][10] . Number of quinazoline derivatives with different substitutions at 2,3,4,6 positions have been reported and studied as antitumor 11 , antibacterial 12 , anticonvulsant 13 , antimalarials 14 and antiviral agents 15 as shown in Table 1.…”