Synthesis, Characterization and Anti-Inflammatory Evaluation of Substituted Quinazolinone Derivatives (original) (raw)
Related papers
2012
S. Bhattacharya, Yusra Ahmad, Meenu Chaudhary* 1 Dr. S. Bhattacharya, Professor, Department of pharmaceutical Chemistry, SIP, Allahabad, Utter Pradesh211003, India 2 Dr. Yusra Ahmed, Associate Professor, Department of Pharmacology, Uttrakhand Technical University, Dehradun, Uttrakhand-248001, India *3 Meenu Chaudhary, Senior Lecturer, Division of Pharmaceutical Sciences, S.G.R.R.I.T.S. Patel Nagar, Dehradun, Uttrakhand-248001, India
Synthesis, Characterization, and Anti-Inflammatory Activity of Newer Quinazolinone Analogs
Journal of Pharmaceutics, 2013
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.
Some 4(3H)-quinazolinone and its derivatives with potential anti-inflammatory properties were synthesized from the reaction of anthranilamide and the proper triethyl orthoacetate, triethyl orthoformate and triethyl orthobenzoate. All the compounds synthesized were unequivocally confirmed by means of infrared, Nuclear Magnetic Resonance (1 H and 13 C), Gas chromatography Mass Spectrophotometer, and elemental analysis. The quinazolinones were evaluated pharmacologically for their in vivoanti-inflammatory activities by carrageenan-induced rat paw oedema. All the investigated compounds exhibited significant anti-inflammatory activity in the range of 81-96% in comparison to control.
Arkivoc, 2006
Two series of 6,8-disubstituted 2-phenyl-3-[substituted benzothiazol-2-yl]-4(3H)-quinazolinones [3a-m and 4a-m] have been synthesized and characterized by elemental analysis and spectral data. The anti-inflammatory activity of the title compounds (3a-m and 4a-m) was evaluated and the most active compounds were evaluated for COX-1 and COX-2 inhibitory activity and ulcerogenic activity. All the test compounds were administered orally/intraperitoneally at a dose 50 mg/Kg body weight and percentage inhibitions were determined. Further more all the compounds were also tested against Gram negative, Gram positive bacteria and fungi. Among the compounds tested in this study, compounds 2-phenyl-3-(4-methoxybenzothiazol-2-yl)-4(3H)quinazolinone (3e), 2-phenyl-3-(5-methylbenzothiazol-2-yl)-4(3H)-quinazolinone (3f) and 2phenyl-3-(4-6-dimethylbenzothiazol-2-yl)-4(3H)-quinazolinone (3l) showed most prominent anti-inflammatory activity with low gastric ulceration incidence compare to reference standard Indomethacin. Further compounds, 3e, 3f and 3l revealed superior inhibitory profile against COX-2 enzyme, when compared with reference standard Indomethacin. Among all the compounds, compounds 4g and 4j posses a broad spectrum of antibacterial activities against both Gram positive and Gram negative bacteria but insignificant antifungal and anti-inflammatory activity.
Benzoxazinones and quinazolinones have a wide spectrum of biological activity. In this paper we focused on studying the antimicrobial and anti-inflammatory activities of some newly synthesized benzoxazinone and quinazolinone derivatives. Thus we prepared 2-[α-benzoylaminostyryl]-6,8-dibromo-3,1-benzoxazin-4(H)-one 2 which underwent a reaction with primary and secondary amines, and hydrazine hydrate to give compounds 3, 4 and 5, respectively. Treatment of 2 with hydroxylamine hydrochloride, formamide and/or NaN 3 / AcOH afforded compounds 7, 8, 11 and 12, respectively. Also, compound 2 reacted with maleic anhydride, aromatic hydrocarbons and/or active methylene compounds to produce compounds 13, 15a–c and 16, respectively. Most of the newly synthesized compounds showed significant antimicrobial and anti-inflammatory activities comparable to ampicillin, mycostatine and indomethacin positive controls.
Saudi Pharmaceutical Journal, 2014
Some novel 6,8-diiodo-2-methyl-3-substituted-quinazolin-4(3H)-ones bearing sulfonamide derivatives (4-11) were synthesized in good yields and evaluated for their possible antibacterial, anti-inflammatory activities and acute toxicity. The structures of the synthesized compounds were confirmed on the basis of their spectral data and elemental analysis. Their antibacterial activities were evaluated by the agar well diffusion method while their anti-inflammatory activities were evaluated by the carrageenan-induced hind paw edema test. All the tested compounds showed considerable antibacterial activities and high to moderate anti-inflammatory activities that last for 12 h compared to ibuprofen. All the tested compounds showed no toxic symptoms or mortality rates 24 h post-administration at tested anti-inflammatory doses. In addition, LD50 for all tested compounds was higher than that for ibuprofen implying their good safety margin. The obtained results showed that the most active compounds could be useful as a template for future design, modification and investigation to produce more active analogs.
Beni-Suef University Journal of Basic and Applied Sciences
Background: Quinazolin-4(1H)-one nucleus has attracted the attention of medicinal chemists due to their clinical uses. Modification of quinazolinone ring for the development of pharmaceutical and clinical compound for its antiinflammatory potential. Results: In vitro anti-inflammatory activity of the synthesized compounds was performed by using egg albumin protein denaturation assay, while in vivo anti-inflammatory activity was performed by using carrageenan-induced rat paw edema and cotton pellet-induced granuloma pouch model. In the present study, we synthesized a new series of 2,3-disubstituted quinazolin-4(1H)-one derivatives and evaluated their in vivo, in vitro anti-inflammatory effect. Their chemical structures are confirmed by FTIR, 1 HNMR, and mass spectrum. Among all the synthesized compounds, G1 and G3 exhibit the significant anti-inflammatory activity by inhibiting release of inflammatory mediators like prostaglandin, histamine, and serotonin. in both in vivo and in vitro models as compared to compound G2. Conclusion: These synthesized compounds showed anti-inflammatory activity by inhibiting prostaglandins and COX enzymes. So, all test compounds may be used for both inflammation as well as inflammation-induced cancer therapy. Future various screening method related with inflammation and inflammation-induced cancer needs to be evaluated pre-clinically and clinically.
Synthesis and Biochemical Evaluation of Some Novel Anti-inflammatory Quinazolines
2011
This study was carried out to synthesis of some novel of anti-inflammatory triazoloquinazoline and triazinoquinazoline derivatives. When compound 2 was reacted with sulfa merazine the thioureido derivative 3 was obtained. Refluxing of compound 3 with hydrazine hydrate in ethanol afforded the N-aminoquinazoline derivative 4. When compound 4 was reacted with aromatic aldehydes with aromatic aldehydes in acetic acid containing fused sodium acetate, triazoloquinazoline derivatives 5 – 7 were produced. In a similar manner, acetic anhydride and/or 2- chlorobenzoylcholoride were reacted with compound 4 to furnish the triazoloquinazoline derivatives 8, 9, respectively. In addition, the corresponding triazinoquinazoline derivative 11 was obtained via reaction of compound 4 with ethyl chloroacetate. The triazoloquinazoline 16 was obtained in good yield via reaction of 4 with diethyloxalate. The results of the pharmacological study indicated that some of the derivatives which were tested, espe...
Various 2-(substitutedphenylmethyleneimino)aminoacetylmethylene-3-(2 0 -substitutedindol-3 0 -yl)-halosubstituted-4(3H)quinazolinones (5a-5i) and 2-(substituted phenylaminomethyleneacetyl-4 0 -oxo-1 0 -thiazolidinyl-3-(2 00 -substitutedindol-3 00 -yl) 4(3H)-quinazolinones (6a-6i) have been synthesized in the present studies. The structure of these compounds have been elucidated by elemental (C, H, N) and spectral (IR, 1 H NMR and mass) analysis. Furthermore, above said compounds were evaluated for their anti-inflammatory, analgesic, ulcerogenic activities and acute toxicity study. Compound 6d was found to be most potent. Compound exihibiting less ulcerogenic liability and ALD 50 > 2000 mg/kg po. #
Quinazolinone is a compound made up of two fused six member simple aromatic benzene ring and a number of substituted quinazolinone are known for their biological importance like anticancer, antibiotic , anti-microbial, anti-HIV, anti-oxidant, anti-tubercular, anti-malarial, anti-viral, anti-psychotics and anti-inflammatory activity. In the present investigation an attempt has been made for the 1,2 di-substituted quinazolinone, using N-substituted derivative of aniline & derivative of aldehyde. Further these 1,2 di-substituted quinazolinone has condensed with various primary amine containing drug like acetamide, sulfanilamide, thiourea and with aromatic amine like o-chloro benzoic acid, derivative of aniline and derivative of aldehyde. The synthesized compound have been established on the basis of Infra-Red, Nuclear Magnetic Resonance spectral data, Thin Layer Chromatography and Melting Point or Boiling Point .These compound are also screened for biological activity like anti-microbial activity using standard disk method by measuring inhibition of zone. Ceftriaxone was used as standard drug. The synthesized compound was shown to good anti-microbial activity as compared with standard.