Synthesis, Anti‐inflammatory and Analgesic Synthesis, Anti‐inflammatory and Analgesic New 4(3H)‐Quinazolinone Derivatives

Abstract

4(3H)-quinazolinone and pyrazole derivatives have been shown to have analgesic and anti-inflammatory properties. In this study, 14 new 3-methyl-4(3H)quinazolinone derivatives bearing 2-[1'-phenyl-3'-(substituted-phenyl)-2'-propenylidene]hydrazino or 2[5'-(substituted phenyl)-3'-phenyl-2'-pyrazolin-1'-yl] groups have been synthesized with the aim of obtaining new analgesic and anti-inflammatory leads. The structures were elucidated by means of UV, IR, 1H-NMR, 13C-NMR, mass spectroscopy, and elemental analysis data. The anti-inflammatory activities of the synthesized compounds were determined by carrageenan-induced hind paw edema test in mice. All the compounds showed statistically significant effects. For analgesic activity assessment, p-benzoquinone-induced writhing test was applied in mice. The results obtained were in accordance with the anti-inflammatory activity tests.

Crystal structure of 5-methyl-2-phenyl-4-[1-(4-p-tolyl-thiazol-2-ylamino)- ethylidene]-2,4-dihydropyrazol-3-one, C22H20N4OS

“…Over the past fewyears, both pyrazoles and their derivatives have attracted much attention because they possess awide spectrum of biological activities, such as antimicrobial [1], anti-inflammatory [2], antiviral [ 3],a nticancer [4], insecticidal [5], herbicidal [6]a nd plantgrowthregulatory [7]. Many pyrazoles are currently being tested and clinically evaluated as potential new drugs [8,9].Also theaminothiazole ring system hasauseful structural element in medicinal chemistry [10][11][12][13][14].…”

In vivo metabolism of 2-[1′-phenyl-3′-(3-chlorophenyl)-2′-propenylyden]hydraz ino-3-methyl-4(3H)-quinazolinone in rats

“…hydrazino-3-methyl-4(3H)-quinazolinone (substrate), 2-hydrazino-3-methyl-4(3H)-quinazolinone (M1) and 3-(3-chlorophenyl)-1-phenylprop-2-en-1-one (M2) were synthesized as reported previously [22]. All the reagents used for chromatographic separation were of analytical grade and obtained from Fluka and Merck.…”

“…hydrazide compounds, produce the corresponding hydrolytic products [20,21]. We therefore decided to investigate the in vivo metabolism of 2-[ 1'-phenyl-3'-(3-chlorophenyl)-2'-propenylyden] hydrazino-3-methyl-4(3H)-quinazolinone containing a large quinazolinone moiety that had previously been synthesized and determined to be an effective analgesic and anti-inflammatory agent [22].…”

Synthesis, characterization and evaluation of in vitro antioxidant and anti-inflammatory activity of 2-(4-oxo-2-phenylquinazolin-3(4H)-yl) substituted acetic acids

“…Among a wide variety of nitrogen heterocycles that have been explored for developing pharmaceutically, quinazolinone plays an important role in medicinal chemistry and subsequently have emerged as a pharmacophore . Quinazolinones are classes of fused heterocycles that are of considerable interest because of the diverse range of their biological activities such as farnesyltransferase, gastric H+/K+-ATPase and MAP kinase p38 inhibitory properties [1],anticancer [2][3][4][5], antiulcer [6],anti-tubercular [7], anti-bacterial and antifungal [8][9][10][11],anti-HIV [12],CNS depressant [13] , anticonvulsant [14], antihelmintic [15], analgesic and antiinflammatory [16][17][18], antihypertensive [19], antidiabetic [20] and anti-oxidant activities [21].…”