New quinazolinone–pyrimidine hybrids: Synthesis, anti-inflammatory, and ulcerogenicity studies

Abbas, Samir Y.; Awadallah, Fadi M.; Ibrahin, Nashwa A.; Said, Eman G.; Kamel, Gehan M.

doi:10.1016/j.ejmech.2012.03.050

Cited by 82 publications

(47 citation statements)

References 39 publications

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“…The synthesis of 3-aryl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one (3a-e) was carried out according the synthetic route shown in Scheme 1 involving treatment of substituted anilines with carbon disulfide and sodium hydroxide in dimethyl sulfoxide to afford sodium dithiocarbamates (2). Quinazolin-4(1H)-ones (3a-e) were * Correspondence: aamersaeed@yahoo.com obtained by adding methyl anthranilate to the solution of the latter in ethanol using anhydrous potassium carbonate as a weak base.…”

Section: Resultsmentioning

confidence: 99%

“…The solid obtained was filtered, washed, and recrystallized from ethanol to give methyl substituted phenylcarbamodithioate (2). To the solution of 2 (0.01 mol) in ethanol (20 mL) methyl anthranilate (0.01 mol) and anhydrous potassium carbonate (100 mg) were added and the reaction mixture was refluxed for 25 h. The reaction mixture was added to ice cold water and a solid product was obtained.…”

Section: General Procedures For the Synthesis Of 3-aryl-2-thioxo-23-dmentioning

confidence: 99%

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Synthesis and characterization of new (E)-N''-(substituted benzylidene)-2-(3-(2-methyl)-4-oxo-3,4-dihydroquinazolin-2-ylthio)acetohydrazides

Saeed¹,

Mahmood²,

Flörke³

2014

Turk J Chem

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A small library of new azomethine derivatives of 3-aryl-2-thioxo-2,3-dihydroquinazolin-4(1 H) -ones was synthesized. The key intermediates 2-thioxo-quinazolinones (3a-e), obtained in 2 steps from the corresponding anilines, were treated with methyl chloroacetate to afford S-substituted esters (4a,d), which were then converted into corresponding acetohydrazides (5a,d). Further, acetohydrazide (5d) was converted to the azomethines derivatives (6a-k) by reacting with a number of suitably substituted benzaldehydes. FTIR, 1 H NMR, 13 C NMR, GC-MS, and elemental analyses were used to confirm the assigned structures of the synthesized compounds. Further, compounds 3a, 5, and 6j were also confirmed by X-ray diffraction data.

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Section: Resultsmentioning

confidence: 99%

Section: General Procedures For the Synthesis Of 3-aryl-2-thioxo-23-dmentioning

confidence: 99%

Synthesis and characterization of new (E)-N''-(substituted benzylidene)-2-(3-(2-methyl)-4-oxo-3,4-dihydroquinazolin-2-ylthio)acetohydrazides

Saeed¹,

Mahmood²,

Flörke³

2014

Turk J Chem

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“…The synthesis of these quinazolinone derivatives is not only of interest from an economical point of view, but in many cases also offers considerable advantages in terms of yield, selectivity, and simplicity of the reaction procedure. Quinazoline-4(3H)-ones are versatile nitrogen heterocyclic compounds, displaying a broad spectrum of biological and pharmacological activities such as anti-fungal (Liu et al, 2006), anti-histaminic (Lemura et al, 1989), anti-cancer (Abbas et al, 2012), anti-viral (Dinakaran et al, 2003), anti-inflammatory (Amin et al, 2010), and anti-bacterial (Kini and Grover, 2006). Recent studies assert that some sulfonamides also work as anti-inflammatory drugs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structure–activity relationships, and bioactivity evaluation of 6-bromo-quinazolinone derivatives

et al. 2014

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6-Bromo-quinazolinone derivatives were prepared and evaluated for the ability to inhibit cyclooxygenase-2 (COX-2). An extensive structure-activity relationship work was carried out, thus some potent and selective COX-2 inhibitors were identified. The key compound isothiocyanate was prepared through a simple and ecological method using di-2-pyridyl thionocarbonate in substitution of the thiophosgene, a potential air pollutant. The cyclization reaction of intermediate derivatives was developed through the methods reporting by Wamhoff. The anti-inflammatory activity of the derivatives (5-12) was evaluated by determining (by Western blot) the expression of cyclooxygenase (COX)-2, of inducible NO synthase (iNOS) and of intercellular adhesion molecule-1 (ICAM-1). The biological assays showed that the derivatives 7, 9, 10, 12 act as potent inhibitors of COX-2, iNOS, and ICAM-1 expression in human keratinocytes NCTC-2544 cells. This work showed that the new derivatives could be used as a novel class of antiinflammatory agents.

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“…These two compounds also showed more COX-2 inhibition as compared to COX-1 inhibition. 15 Tetrahydropyrimidine and adamantane hybrids were synthesized and evaluated for their antiinflammatory activity. It was found that compounds that contain a methyl group or benzyl group at position # 1 of the tetrahydropyrimidine ring showed excellent antiinflammatory activity, while those containing a phenyl group were found to be less active.…”

Section: Pyrimidine Dihydropyrimidines Tetrahydropyrimidine and Tementioning

confidence: 99%

“…13,14 In designing new drug molecules, synthesis of the hybrid molecular technique is also being used in addition to the synthesis of new derivatives. 15 In molecular hybridization constituents are linked directly, with the help of some linker, or the active structural parts are merged into a single molecule. 16 In our work, we studied the hybrid molecules prepared by a combination of NSAIDs with other synthetic and natural molecules.…”

Section: Introductionmentioning

confidence: 99%

Hybrid organic molecules as antiinflammatory agents; a review of structural features and biological activity

Mohsin¹,

Ahmad²

2018

Turk J Chem

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Nonsteroidal antiinflammatory drugs (NSAIDs) are widely used for the treatment of pain and inflammation.Some undesirable effects are linked with NSAIDs such as the gastrointestinal tract (GIT) toxicity and cardiovascular disturbances. At present the preparation of a hybrid molecular technique is being used to produce new analgesic and antiinflammatory molecules. Attachment of NSAIDs with nitric oxide and hydrogen sulfide releasing molecules produced some gastroprotective agents with improved analgesic and antiinflammatory activities. Combination of NSAIDs with different biologically active 5-membered, 6-membered, and condensed heterocyclic rings has also led to the formation of some potent molecules. Some of these hybrid molecules, e.g., ibuprofen-thiazole, exhibited less GIT toxicity, while others showed selectivity for COX-2 enzyme, e.g., quinazolinone-pyrimidine and benzothiophene-rhodanine hybrids. COX-2 selectivity was also exhibited by hybrids of NSAIDs with natural molecules such as salicylates-resveratrol, chromoneoxindole, and chrysin-indole-pyrazole. The preparation of new hybrid molecules is significant because they can serve as a lead compound for the discovery and development of safer analgesic and antiinflammatory agents.

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New quinazolinone–pyrimidine hybrids: Synthesis, anti-inflammatory, and ulcerogenicity studies

Cited by 82 publications

References 39 publications

Synthesis and characterization of new (E)-N''-(substituted benzylidene)-2-(3-(2-methyl)-4-oxo-3,4-dihydroquinazolin-2-ylthio)acetohydrazides

Synthesis and characterization of new (E)-N''-(substituted benzylidene)-2-(3-(2-methyl)-4-oxo-3,4-dihydroquinazolin-2-ylthio)acetohydrazides

Synthesis, structure–activity relationships, and bioactivity evaluation of 6-bromo-quinazolinone derivatives

Hybrid organic molecules as antiinflammatory agents; a review of structural features and biological activity

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