Synthesis of 3-(2-pyridyl)-2-substituted-quinazolin-4(3H)-ones as new analgesic and anti-inflammatory agents

Alagarsamy, V.; Solomon, V. Raja; Murugan, M.; Sankaranarayanan, Ranjini; Periyasamy, P.C.; Deepa, R.; Anandkumar, T. Durai

doi:10.1016/j.biopha.2006.10.003

Cited by 15 publications

(11 citation statements)

References 15 publications

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“…The chemistry of Quinazolines class compounds are very promising because it shows wide spectram of biological activity like analgesic and anti-inflammatoryanti, antimicrobial, antihypertensive, anticancer [1][2][3][4] etc. activities.…”

Section: Introductionmentioning

confidence: 99%

Separation of Amino Acids Based on Thin-Layer Chromatography by a Novel Quinazoline Based Anti-Microbial Agent

Sen¹,

Sarkar²,

Kundu³

et al. 2012

AJAC

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A newly designed quinazoline based compound, 6-pyridin-2-yl-5,6-dihydro-benzo[4,5]imidazo[1,2-c] quinazoline (PDBIQ) has shown the ability for the easy detection of nineteen amino acids on thin-layer chromatography plates as a spray reagent. This new reagent enabled to produce various distinguishable colors with amino acids with different R<sub>F</sub> values. The detection limits and the binding ability of PDBIQ with amino acids have been calculated. PDBIQ is also able to detect aminoacids from hydrolised seed protein. The title compound also exhibited profound inhibitory action against some gm (+ve) and gm (-ve) bacterial organisms. This paper deals with synthesis, spectroscopic application and biological evaluation of the organic moity

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Section: Introductionmentioning

confidence: 99%

Separation of Amino Acids Based on Thin-Layer Chromatography by a Novel Quinazoline Based Anti-Microbial Agent

Sen¹,

Sarkar²,

Kundu³

et al. 2012

AJAC

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“…The reactions were catalyzed with triethylamine (TEA) and maintained at 70-80°C. An alcohol (6) and diol (7) with imidazoquinazoline ring were obtained with an equimolar amount of EO or 2-molar excess of EO as described in BIntroduction^ [4,5]. It was expected to produce etherols (9)(10)(11) with the imidazoquinazoline ring in the reaction of (4) with 3-molarexcess of EO, under conditions analogous to the synthesis of (6) and (7).…”

Section: Resultsmentioning

confidence: 99%

“…The compound (4) could be reacted with ethylene oxide (EO, 5), and then, alcohol (6) [4] and diol (7) [5] with the imidazoquinazoline rings were successively produced according to the scheme shown in Fig. 2.…”

Section: Introductionmentioning

confidence: 99%

“…Compounds containing imidazoquinoline and imidazoquinazoline rings have interesting properties. Quinazoline derivatives have a wide spectrum of biological properties, which allow their use in the production of antiinflammatory [6], anti-parasitic [7], anti-histamine [8], antidiuretic [9], and anti-cancer [10] drugs. In turn, imidazoquinazoline derivatives have wide application in medicine and pharmacy due to their anti-tumor, anti-viral, antibacterial or anti-convulsive, and anti-oxidative activity [11][12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

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Unprecedented reaction course of 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione with 3-M excess of ethylene oxide

et al. 2019

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The reaction of 1-phenyl-2H,6H-imidazo[1,5-c]quinazolino-3,5-dione (4) with 3-molar excess ethylene oxide was described. The resulting product was characterized by spectroscopic techniques (1 H-, 13 C-NMR, IR, and UV) and by X-ray crystallography. It was expected to produce a product of the subsequent reaction in the hydroxyl groups of the initially formed diol-1-phenyl-2,6-bis(2-hydroxyethyl)imidazo[1,5-c]quinazoline-3,5-dione (7) with ethylene oxide (5). However, crystallographic studies revealed that the proper and only product of the reaction is 3-{2-[1,3-bis(2hydroxyethyl)-2-oxo-4-phenylimidazolidin-5-yl]phenyl}-1,3-oxazolidin-2-one (8). This product was formed by quinazoline ring opening which occurred in the presence of more than 2-molar excess ethylene oxide. In the work, the exemplary reaction mechanism explaining the formation of the unexpected product was proposed. In order to understand the reasons of quinazoline ring opening, the quantum mechanical modeling was performed. Energy of transition states indicated that the reaction with the third mole of ethylene oxide was controlled by kinetics.

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“…The quinazolinone skeleton is a frequently encountered heterocycle in medicinal chemistry literature with applications including analgesic-anti-inflammatory 1 , antibacterial 2 , antimalarial 3 , CNS depressant-anticonvulsant 4 , antihistaminic 5 , antiviral 6 , antitumor 7 and antitubercular 8 activities.…”

Section: Introductionmentioning

confidence: 99%

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2012

IJPSR

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Some new series of 3-(4-substituted-phenyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one, 3-(4-substituted-phenyl)-2-(methylthio)quinazolin-4(3H)-one and 3-(4-substituted-phenyl)-2-hydrazinylquinazolin-4(3H)-one were synthesized by cyclization of 4-substituted-phenylcarbamodithioate with methyl anthranilate followed by reaction with dimethylsulphate and then prepared compound was refluxed with hydrazinehydrate respectively. The starting material 4-substituted-phenylcarbamodithioate was synthesized from 4-substituted-aniline. The title compounds were investigated for antibacterial and antifungal activity by disc diffusion technique. Compound IIa, IIb and IIIa showed moderate activity against B. subtilis, E. coli and A. niger as compared to standard drug. Compound IIIb and Iva exhibited good activity against A. niger. Compound IIIc and IVc was found to be most active compound against E. coli and moderately active against B. subtilis and A. niger, of the prepared series.

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Synthesis of 3-(2-pyridyl)-2-substituted-quinazolin-4(3H)-ones as new analgesic and anti-inflammatory agents

Cited by 15 publications

References 15 publications

Separation of Amino Acids Based on Thin-Layer Chromatography by a Novel Quinazoline Based Anti-Microbial Agent

Separation of Amino Acids Based on Thin-Layer Chromatography by a Novel Quinazoline Based Anti-Microbial Agent

Unprecedented reaction course of 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione with 3-M excess of ethylene oxide

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