Antimicrobial studies of some novel quinazolinones fused with [1,2,4]-triazole, [1,2,4]-triazine and [1,2,4,5]-tetrazine rings

Pandey, Sarvesh Kumar; Singh, Abhishek; Singh, Ashutosh; Nizamuddin, .

doi:10.1016/j.ejmech.2008.05.033

Cited by 115 publications

(42 citation statements)

References 15 publications

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“…Sheldrick, G. M. (2008 Heterocyclic compounds have so far been synthesized mainly due to the wide range of biological activities. At present, the role of heterocyclic compounds has become increasingly important in designing new class of structural entities of medicinal importance (Pandey et al, 2009;Nasser, 2000). Imidazole is a nitrogen containing heterocyclic ring which possesses biological and pharmaceutical importance (Ozkay, et al, 2010).…”

Section: Methodsmentioning

confidence: 99%

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2-Hydroxymethyl-1,3-dimethyl-1H-imidazol-3-ium triiodide

et al. 2013

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Section: Methodsmentioning

confidence: 99%

“…For the importance of heterocyclic compounds and their applications, see: Pandey et al (2009);Nasser (2000). For the biological activity of imidazole and imidazolium derivatives, see: Ucucu et al (2001); Dominianni et al (1989); Ozkay et al (2010).…”

Section: Related Literaturementioning

confidence: 99%

2-Hydroxymethyl-1,3-dimethyl-1H-imidazol-3-ium triiodide

et al. 2013

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“…-A mixture of 2-5 (0.01 mol) and hydrazine hydrate (1.0 g, 0.02 mol) in butanol (30 mL) was refluxed for 5 h. After cooling the reaction mixture was poured onto ice water and the solid obtained was recrystallized from dioxane to give 6-9, respectively. N-substituted-4-(9-oxo-2-phenyl [1,2,4]triazolo [5,1-b]quinazolin-3(9H)-yl)benzenesulfonamides (10)(11)(12)(13)(14)(15)(16)(17)(18). -A mixture of 6-8 (0.01 mol) and aromatic aldehyde (0.01 mol) in glacial acetic acid (20 mL) containing fused sodium acetate (0.5 g) was heated under reflux for 4 h, the solvent was concentrated and the residue was recrystallized from dioxane to give 10-18, respectively.…”

Section: Methodsmentioning

confidence: 99%

“…From the literature survey, it was found that the corresponding triazoloquinazolinones seemed to be more potent than tetrazinoquinazolinones and indolotriazinoquinazolinones. The presence of triazole nucleus at N-1 and C-2 of quinazolinone ring works better for antimicrobial activity of this series of compounds than the others (14) which showed moderate to good antifungal activity (15). Moreover, sulfonamides constitute an important class of drugs, with several types of pharmacological activities, specially antimicrobial activities (6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19).…”

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Synthesis and pharmacophore modeling of novel quinazolines bearing a biologically active sulfonamide moiety

Ghorab

Ismail²,

Radwan³

et al. 2013

Acta Pharmaceutica

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In the present work, interaction of the strategic starting material, methyl 2-isothiocyanatobenzoate (1), with sulfa drugs resulted in the formation of methyl 2-[3-(4-(N-substituted sulfamoyl)phenyl)thioureido] benzoates 2-5, which upon reaction with hydrazine hydrate afforded N-amino derivatives 6-9. Triazoloquinazoline derivatives 10-18 were obtained via reaction of compounds 6-8 with aromatic aldehydes. Also, the reaction of compound 8 with formic acid gave the corresponding triazoloquinazoline derivative 19. Triazinoquinazoline derivatives 22, 23 were obtained via reaction of N-amino derivatives 6 or 8 with ethyl chloroacetate. Interaction of 6 with diethyloxalate yielded triazoloquinazoline 26. The synthesized compounds were screened for their in vitro antimicrobial activities and some of them exhibited promising antibacterial activity compared to ampicillin as positive control. Compounds that revealed significant activity are able to satisfy effectively the proposed pharmacophore geometry.

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“…They exhibit diverse biological properties like, antimicrobial, [1][2][3] antiviral, 4) anticancer, 5) anticonvulsant, 6) CNS depressant 7) and antihypertensive activity. 8) Amongst these, C-2 and N-3 disubstituted quinazolines with aryl and heteroaryl groups at N-3 position have shown enhanced anti-inflammatory activity as a result of their nitric oxide inhibitory activities.…”

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confidence: 99%

A Study of Anti-inflammatory and Analgesic Activity of New 2,3-Disubstituted 1,2-Dihydroquinazolin-4(3H)-one Derivative and Its Transition Metal Complexes

Hunoor

Patil

Badiger

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Quinazolinones and their derivatives have drawn much attention owing to their various pharmacological properties. They exhibit diverse biological properties like, antimicrobial, [1][2][3] antiviral, 4) anticancer, 5) anticonvulsant, 6) CNS depressant 7) and antihypertensive activity. 8) Amongst these, C-2 and N-3 disubstituted quinazolines with aryl and heteroaryl groups at N-3 position have shown enhanced anti-inflammatory activity as a result of their nitric oxide inhibitory activities. 9)A good deal of research has been carried out on the coordinating behavior of 2,3-disubstituted quinazolin-4(3H)-ones which offer various potential donor sites. [10][11][12][13][14][15] In comparison, 2,3-disubstituted 1,2-dihydroquinazolinones and their metal complexes are not much explored. We have recently reported the synthesis of 1,2-dihydroquinazolinones by the condensation of 2-aminobenzoylhydrazide with aryl and heteroaryl aldehydes and their chelating behavior towards transition and inner transition metal ions. [16][17][18][19][20][21][22] Their antimicrobial potency is also tested against different bacterial and fungal strains. Our continued research in this perspective resulted in a new approach, in which 2-aminobenzoylhydrazide is converted to hydrazone in the first step. The reaction of this hydrazone with aromatic aldehydes results in the formation of biologically active 1,2-dihydroquinazolinones, with different substituent at C-2 and N-3 positions.Aroylhydrazones of salicylaldehyde, which typically act as tridentate planar chelate coordinating through phenolic oxygen, amide oxygen and imine nitrogen (Chart 1a) are known for their interesting biological activities.23) Keeping the framework of coordinating sites of aroylhydrazones intact, we have designed quinazoline analogue (Chart 1b) of aroylhydrazone of o-hydroxyacetophenone which is structurally similar with aroylhydrazones of salicylaldehyde. Recent investigation show that coordination of organic molecules and anti-inflammatory drugs with Co(II), Ni(II), Cu(II), Fe(II) and Zn(II) metal ions resulted in the enhancement of their activity. [24][25][26] Thus, the present article charts the progress of our methodology in the synthesis of new 1,2-dihydroquinazolin-4(3H)-one derivative viz., 2-hydroxy-2-ethyl-(3-carboxylideneamino)-3-(2-(4-methyl-phenyl))-1,2-dihydroquinazolin-4(3H)-one (HECMDQ) (C1) with different substituent at C-2 and N-3 positions and its coordinating behavior towards Co(II), Ni(II), Cu(II) and Zn(II) ions. The results of analgesic activity are impressive and perhaps suggestive of future success. ExperimentalMaterials Methylanthranilate (S.D. Fine Chemicals, India), hydrazinehydrate (Spectrochem, India) o-hydroxyacetophenone (Himedia, India), pmethylbenzaldehyde (Spectrochem, India) and metal(II) chlorides used in the present study were of AR grade and used as supplied. All the solvents were distilled before use. o-Aminobenzoylhydrazide 27) and o-hydroxyacetophenone-o-aminobenzoylhydrazone 28) were prepared following the literature procedures.P...

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Antimicrobial studies of some novel quinazolinones fused with [1,2,4]-triazole, [1,2,4]-triazine and [1,2,4,5]-tetrazine rings

Cited by 115 publications

References 15 publications

2-Hydroxymethyl-1,3-dimethyl-1H-imidazol-3-ium triiodide

2-Hydroxymethyl-1,3-dimethyl-1H-imidazol-3-ium triiodide

Synthesis and pharmacophore modeling of novel quinazolines bearing a biologically active sulfonamide moiety

A Study of Anti-inflammatory and Analgesic Activity of New 2,3-Disubstituted 1,2-Dihydroquinazolin-4(3H)-one Derivative and Its Transition Metal Complexes

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