AntiHIV, antibacterial and antifungal activities of some novel 2-methyl-3-(substituted methylamino)-(3H)-quinazolin-4-ones

Alagarsamy, V.; Murugesan, S.; Dhanabal, K; Murugan, Moorthiraman; Clercq, Erik De

doi:10.4103/0250-474x.33167

Cited by 44 publications

(26 citation statements)

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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%

“…The 3-substitutions were reported in substituted phenyl ring moieties (9), bridged phenyl rings (10), heterocyclic rings (11) and aliphatic systems (12). Also, 2,3-disubstituted-4(3H)-quinazolinones were reported to possess antimicrobial properties (13). From the literature survey, it was found that the corresponding triazoloquinazolinones seemed to be more potent than tetrazinoquinazolinones and indolotriazinoquinazolinones.…”

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confidence: 99%

“…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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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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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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“…The anti-HIV activity of 2-phenyl-3-substituted quinazolin-4-(3H)-ones. the 2-phenyl-3-substituted quinazolin-4-(3H)-ones [59][60][61]. A large number of quinazolines have been synthesized and studied for wide range of anti-viral activity.…”

Section: Compound 45 R=cooh R1= P-c6h5mentioning

confidence: 99%

A Review on a Highly Important Hetrocycle Quinazolinone Compounds and their Diverse Biological Activities

2016

European Reviews of Chemical Research

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Quinazolinone and their derivatives have been studied extensively for various biological activities such as anti-inflammatory, antimicrobial, anticancer, anticonvulsant and anti-HIV activity etc. The purpose of this review was to collate literature work reported by researchers on quinazoline for their various pharmacological activities. Quinazolinone derivatives are one of the most active classes of compounds possessing a wide spectrum of biological activity. Recently several scientists have been reported that introduction of various heterocyclic moieties at quinazolinone nucleus modulate the activity. Various derivatives of quinazolinone have been synthesized and evaluated for their biological activities. This review might be helpful in the development of these novel lead molecules to potential drug candidates for future prospect.Keywords: Quinazoline, antimicrobial, Anti HIV, Anti cancer, biologically active. IntroductionHeterocyclic chemistry comprises at least half of all organic chemistry research worldwide. In particular, heterocyclic structures form the basis of many pharmaceutical, agrochemical and veterinary products. Quinazoline (1) are classes of fused heterocycles that are of considerable interest because of the diverse range of their biological activities such as, antimicrobial, anticancer, anticonvulsant, anti-tubercular, etc [1][2][3][4][5]. Quinazolin is a heterocyclic compound consists of two fused six membered simple aromatic rings, a benzene ring and a pyrimidine ring. The quinazolin nucleus has attracted the attention of medicinal chemists due to its well known anticancer activity, and many substituted quinazolin derivatives have recently earned great interest in chemotherapy as antitumor drugs [6]. Pharmacologically quinazolin particularly quinazolin-4-one (2) or quinazolinone are the most important classes of heterocyclic compounds. Quinazolin-4-one is synthesized when the keto group is introduced in the pyrimidine ring of quinazolin. Quinazolinone compounds possess versatile biological activities; such as anticancer [7][8]

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“…Methaqualone was synthesized for the first time in 1951 and it is the most well-known synthetic quinazolinone drug famous for its sedative hypnotic effects. 9 The structural diversity of quinazolinones has been broadened with the discovery of asperlicin along with asperlicins B, C, D and E. [10][11][12][13][14] The broad spectrum of activity has been further facilitated by the synthetic versatility of quinazolinones which allows the generation of a large number of structurally diverse molecules. 15 Taking into consideration the use of quinazolinone derivatives in the treatment of some diseases, mentioned above, we have tested the antibacterial activity of the synthesized compounds 1 and 2 using strains of staphylococcus aureus, Bacillus …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Activity of 7-chloro-2–methyl-4H-benzo[d][1,3]–oxazin-4-one and 3–amino-7-chloro-2-methyl quinazolin-4(3H)–one

Osarumwense¹,

Iyekowa²

2017

TJNPR

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AntiHIV, antibacterial and antifungal activities of some novel 2-methyl-3-(substituted methylamino)-(3H)-quinazolin-4-ones

Cited by 44 publications

References 0 publications

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

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

A Review on a Highly Important Hetrocycle Quinazolinone Compounds and their Diverse Biological Activities

Synthesis and Antibacterial Activity of 7-chloro-2–methyl-4H-benzo[d][1,3]–oxazin-4-one and 3–amino-7-chloro-2-methyl quinazolin-4(3H)–one

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