Synthesis and analgesic-antiinflammatory activities of novel acylarylhydrazones with a 5-phenyl-4-R-3-pyrrolyl-acyl moiety (original) (raw)
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Medicinal Chemistry Research
A variety of novel 3-(3-methoxyphenyl)-2-substituted amino-quinazolin-4(3H)-ones were synthesized by reacting the amino group of 2-hydrazino-3-(3-methoxyphenyl)-quinazolin-4(3H)-one with a variety of aldehydes and ketones. The starting material 2-hydrazino-3-(3-methoxyphenyl)-quinazolin-4(3H)-one was synthesized from 3-methoxy aniline. The title compounds were investigated for analgesic, anti-inflammatory, and ulcerogenic behavior. Among these the compound 2-(1-methyl butylidene-hydrazino)-3-(3-methoxyphenyl)-3H-quinazolin-4-one (AS3) emerged as the most active compound for the analgesic activity, while the compound 2-(1-ethyl propylidene-hydrazino)-3-(3-methyoxyphenyl)-3H-quinazolin-4-one (AS2) showed most potent anti-inflammatory activity of the series and these compounds are moderately more potent when compared to the reference standard diclofenac sodium. Interestingly the test compounds showed only mild ulcerogenic potential when compared to acetylsalicylic acid.
Chemical Biology & Drug Design, 2009
A new series of 3-(3-ethylphenyl)-2-substituted hydrazino-3H-quinazolin-4-ones were synthesized by reacting the amino group of 2-hydrazino-3-(3ethylphenyl)-3H-quinazolin-4-one with a variety of aldehydes and ketones. The title compounds were investigated for analgesic, anti-inflammatory and ulcerogenic index behavior. The compound 2-(N¢-3-pentylidene-hydrazino)-3-(3-ethylphenyl)-3H-quinazolin-4-one (AS2) emerged as the most active compound in exhibiting analgesic activity and the compound 2-(N¢-2-pentylidene-hydrazino)-3-(3ethylphenyl)-3H-quinazolin-4-one (AS3) emerged as the most active compound in exhibiting antiinflammatory activity; and these compounds are moderately potent when compared with the reference standard diclofenac sodium. Interestingly, the test compounds showed only mild ulcerogenic potential when compared with aspirin.
Acta Pharmaceutica, 2000
Nonsteroidal anti-inflammatory drugs (NSAIDs) are commonly prescribed for the treatment of acute and chronic inflammation, pain and fever. However, long-term clinical usage of NSAIDs is associated with significant side effects such as gastrointestinal lesions, bleeding, and nephrotoxicity. Therefore, discovery of new safer anti-inflammatory drugs represents a challenging goal in a research area (1-4). In our ongoing medicinal chemistry research program, we found that quinazolines and condensed quinazolines exhibit potent central nervous system (CNS) activity, including analgesic, anti-inflammatory (5) and anticonvulsant behavior (6). Quinazolin-4(3H)-ones with 2,3-substitution are reported to possess significant analgesic, anti-inflammatory (7, 8) and anticonvulsant 75
Chemical Biology & Drug Design, 2007
A variety of novel 3-butyl-2-substituted amino-3Hquinazolin-4-ones were synthesized by reacting the amino group of 3-butyl-2-hydrazino-3H-quinazolin-4-one with various aldehydes and ketones. The title compounds were investigated for analgesic, anti-inflammatory and ulcerogenic index activities. The compound 3-butyl-2-(1-methylbutylidene-hydrazino)-3H-quinazolin-4-one (AS3) emerged as the most active analgesic agent. Compound 3-butyl-2-(1-ethylpropylidene-hydrazino)-3H-quinazolin-4-one (AS2) emerged as the most active anti-inflammatory agent and is moderately more potent when compared to the reference standard diclofenac sodium. Interestingly, the test compounds showed only mild ulcerogenic potential when compared to aspirin.
Synthesis, Analgesic and Anti-Inflammatory Evaluation of Some New 3H-Quinazolin-4-one Derivatives
Archiv der Pharmazie, 2008
In this study, we have synthesized a series of 3H-quinazolin-4-ones in order to obtain new compounds with potential analgesic and anti-inflammatory activity. The structures of the newly synthesized compounds were confirmed by means of infrared, nuclear magnetic resonance and mass spectroscopy. Some compounds were evaluated for their analgesic and anti-inflammatory activities by writhing and carrageenan-induced rat paw edema tests, respectively. In comparison to the standard drug indomethacine, compounds 4, 6c, 12-14, 16, 18, 19, and 22 induced significant reduction in the writhing response while compounds 6c, 12, 14, 16, 18, and 22 produced a good dose-dependent anti-inflammatory activity. The best dual analgesic / anti-inflammatory relative activity was observed with compounds 6c, 14, 16, 18, and 22.
Archiv Der Pharmazie, 2010
A novel series of 2-substituted-quinazolin-4(3H)-ones were synthesized by reacting 3,5-disubstituted-anthranilic acid with acetic anhydride/benzoyl chloride, which were further reacted with different primary amines to obtain 2,6,8-substituted-quinazolin-4(3H)-ones 6a-f, 7, 8. All the synthesized compounds were characterized and screened for analgesic and anti-inflammatory activities. Compounds 6,8-dibromo-2-phenyl-3-(49-carboxyl phenyl)quinazolin-4(3H)-one 7 and 6,8dibromo-2-phenyl-3-(29-phenylethanoic acid)quinazolin-4(3H)-one 8 displayed good analgesic and anti-inflammatory activity in comparison to the reference standards acetyl salicylic acid and indomethacin, respectively.
A novel series of 6-bromo-2-(4-pyridyl)-quinazolin-4(3H)-ones were synthesized by reacting 5-bromo anthranilic acid with isonictinoly chloride in the presence of acetic anhydride, which were further reacted with p-amino acetophenone to obtain 3-(4-acetylphenyl)-6-bromo-2-(pyridin-4-yl)quinazolin-4(3H)-one (3). Compound 3 underwent further reactions with different aldehydes to afford chalcone derivatives 4-10, which in turn underwent various cyclization reactions to afford cyclized products 15-18. 2-aminothiazole derivatives 12 obtained by reaction of 3 with bromine then with thiourea. Compound 14 obtained by treatment of 11 with KSCN followed by cyclization. Some of the synthesized compounds 4, 5, 12, 14, 15 and 18 were screened for both analgesic and anti-inflammatory activities. All tested compounds showed good analgesic and anti-inflammatory activity in comparison to the reference standard indomethacin. Compounds 4 and 5 showed the highest anti-inflammatory activity, while compounds 14 and 15 showed the highest analgesic activity among all the tested compounds.
Biological and Pharmaceutical Bulletin, 2005
Bacterial infections often produce pain and inflammation. In normal practice, two groups of agents (chemotherapeutic, analgesic and anti-inflammatory) are prescribed simultaneously. Compounds possessing all three activities are not common. Quinazolines and condensed quinazolines exhibit potent antimicrobial 1) and central nervous system (CNS) activities like analgesic, 2) anti-inflammatory 3) and anticonvulsant 4) activities. In view of these facts and to develop our earlier reported 2-phenyl-3-substituted quinazolines, 5) 2,3-disubstituted quinazolines, 6) 2-methyl-3-substituted quinazolin-4-(3H)-ones 7) and 2-methylthio-3-substituted quinazolin-4-(3H)-ones 8) that exhibited good analgesic and anti-inflammatory activities, in the present study we aimed to synthesize some 2-butyl-3-substituted quinazolin-4(3H)-ones. The title compounds were synthesized by nucleophilic substitution of (2-butyl-4-oxo-3H-quinazolin-3-yl)dithiocarbamic acid methyl ester with different amines. The (2-butyl-4-oxo-3H-quinazolin-3-yl)dithiocarbamic acid methyl ester was synthesized by reacting the amino group of 3-amino-2butylquinazoline with carbondisulphide and dimethyl sulphate. The 3-amino-2-butylquinazoline was synthesized from anthranilic acid (Chart 1). Spectral data (IR, NMR and mass
2011
A new series of antiinflammatory active Ibuprofen derivatives comprises quinazolinone moiety was synthesized. Ibuprofen was converted into its acid chloride 1 and reacted with anthranilic acid to give the anilide 2. The anilide 2 was refluxed with acetic anhydride to form benzoxazinone 3. The later on reaction with nitrogen nucleophile such as hydrazine hydrate, gave 3-aminoquinazolinone 4. The compound 4 was used as key starting material to synthesize twelve quinazolinone derivatives 5, 6, 7a-c, 8a-c, 9a-c, and 10. The structures of the synthesized compounds have been established on the basis of spectral and analytical data. All the synthesized compounds have been estimated as anti-inflammatory with minimal ulceroginc effect.