Design, synthesis, and anticonvulsant activity of novel quinazolinone analogues

Gawad, Nagwa M. Abdel; Georgey, Hanan H.; Youssef, Riham M.; Sayed, Nehad A. El

doi:10.1007/s00044-010-9465-4

Cited by 31 publications

(11 citation statements)

References 17 publications

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“…Quinazolin‐4(3 H )‐ones (aka 4‐oxoquinazolines) are a structural sub‐category that have interesting properties such as antitumor ( e. g ., quinazolinone 1 ), anticonvulsant, and antitubercular behavior . In particular, 2‐cyanoquinazolin‐4(3 H )‐ones are useful synthetic scaffolds for the preparation of derivatives with anti‐inflammatory activity, antitumor derivatives of the natural product Luotonin A, and NMDA receptor antagonists .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2‐Cyanoquinazolin‐4‐ones from 3′,5′‐Dichloro‐1H‐spiro(quinazoline‐2,4′‐[1,2,6]thiadiazin)‐4(3H)‐ones

2020

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A two‐step synthesis of five 2‐cyanoquinazolin‐4‐ones starting from 3,4,4,5‐tetrachloro‐4H‐1,2,6‐thiadiazine is presented. The latter reacts with 2‐aminobenzamides to give 3′,5′‐dichloro‐1H‐spiro(quinazoline‐2,4′‐[1,2,6]thiadiazin)‐4(3H)‐ones, which can be degraded with either excess polymer bound triphenylphosphine or catalytic amounts of benzyltriethylammonium iodide to give the 2‐cyanoquinazolin‐4‐ones in 46–97% yields. The single crystal X‐ray diffraction analysis of 2‐cyanoquinazolin‐4(3H)‐one is also reported.

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Section: Introductionmentioning

confidence: 99%

Synthesis of 2‐Cyanoquinazolin‐4‐ones from 3′,5′‐Dichloro‐1H‐spiro(quinazoline‐2,4′‐[1,2,6]thiadiazin)‐4(3H)‐ones

2020

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“…We have reported that S ‐glycosylated hydantoin derivatives showed potent activity against the herpes simplex virus , the human immunodeficiency virus , and the leukemia subpanel . In continuation of our work on the synthesis of novel nucleosides as potential antiviral and antitumor agents and keeping in mind the biological significance of 2‐thioxoquinazolin‐4‐ones , we hereby report the synthesis and spectroscopy of a new series of S ‐alkylated and S ‐glycosylated 3‐substituted 2‐thioxo‐2,3‐dihydro‐1 H ‐benzo[ g ]quinazolin‐4‐one bases (Schemes and ). This is the first time to prepare S ‐glycosides of 3‐substituted 2‐thioxo‐2,3‐dihydro‐1 H ‐benzo[ g ]quinazolin‐4‐ones via new synthetic strategies.…”

Section: Introductionmentioning

confidence: 99%

Simple and Efficient Synthesis of Novel 3‐Substituted 2‐Thioxo‐2,3‐dihydro‐1H‐benzo[g]quinazolin‐4‐ones and Their Reactions with Alkyl Halides and α‐Glycopyranosyl Bromides

Khodair

Elsafi

Alissa

2019

Journal of Heterocyclic Chem

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A series of 3‐substituted 2‐thioxo‐2,3‐dihydro‐1H‐benzo[g]quinazolin‐4‐ones 4a–e were synthesized from the reaction of 3‐aminonaphthalene‐2‐carboxylic acid 1 with isothiocyanate derivatives 2a–e. The alkylation of 4a–e with alkyl halides gave 3‐substituted 2‐alkylsulfanyl‐2,3‐dihydro‐1H‐benzo[g]quinazolin‐4‐ones 5a–o. S‐Glycosylation was carried out via the reaction of 4a–e with glycopyranosyl bromides 7a and 7b under anhydrous alkaline conditions. The structure of the compounds was established as S‐nucleoside and not N‐nucleoside. Conformational analysis has been studied by homonuclear and heteronuclear two‐dimensional NMR methods (2D DFQ‐COSY, heteronuclear multiple quantum coherence, and heteronuclear multiple bond correlation). The S site of alkylation and glycosylation was determined from the 1H and 13C heteronuclear multiple quantum coherence experiments.

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“…Quinazoline is one of the most frequently encountered heterocycles in medicinal chemistry. Quinazoline derivatives have shown significant biological activities such as analgesic , anti‐inflammatory , antifungal , antibacterial , anticancer , antitumor , anti‐HIV , antituberculosis , and anticonvulsant activities. Non‐proteinogenic amino acids are a major component in a number of drugs including β‐lactam antibiotics, glutamate antagonists, and antiviral drugs .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Methyl 2‐(2‐(2‐Arylquinazolin‐4‐yl)oxy) Acetylamino Alkanoates

Megahed

Fathalla

Alsheikh

2018

Journal of Heterocyclic Chem

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A series of methyl 2-(2-(2-arylquinazolin-4-yl)oxy) acetylamino alkanoate have been developed via N,N 0dicyclohexylcarbodiimide coupling of (2-arylquinazolin-4-yloxy) acetic acids with amino acid ester hydrochlorides. The O-substituted carboxylic acids were prepared by two-step reactions from the corresponding 2arylquinazolin-4(3H)-one starting with chemoselective O-alkylation with ethyl chloroacetate and then hydrolysis of the produced esters. The reason for this O-chemoselective behavior of 2-arylquinazolin-4(3H)one toward electrophiles was explained by theoretical density functional theory computational calculations on the model compound 2-phenylquinazolin-4(3H)-one. The antimicrobial activity of the synthesized compounds was evaluated, showing the best inhibition zone for (2-arylquinazolin-4-yloxy) acetic acids, methyl 2-(2-(2-arylquinazolin-4-yl)oxy) acetylamino acetates, and methyl 2-(2-(2-phenylquinazolin-4-yl)oxy) acetylamino-3-methylbutanoate.Scheme 2. Synthesis of methyl 2-(2-(2-arylquinazolin-4-yl)oxy) acetylamino alkanoates 7-8(a-f).

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Design, synthesis, and anticonvulsant activity of novel quinazolinone analogues

Cited by 31 publications

References 17 publications

Synthesis of 2‐Cyanoquinazolin‐4‐ones from 3′,5′‐Dichloro‐1H‐spiro(quinazoline‐2,4′‐[1,2,6]thiadiazin)‐4(3H)‐ones

Synthesis of 2‐Cyanoquinazolin‐4‐ones from 3′,5′‐Dichloro‐1H‐spiro(quinazoline‐2,4′‐[1,2,6]thiadiazin)‐4(3H)‐ones

Simple and Efficient Synthesis of Novel 3‐Substituted 2‐Thioxo‐2,3‐dihydro‐1H‐benzo[g]quinazolin‐4‐ones and Their Reactions with Alkyl Halides and α‐Glycopyranosyl Bromides

Synthesis and Antimicrobial Activity of Methyl 2‐(2‐(2‐Arylquinazolin‐4‐yl)oxy) Acetylamino Alkanoates

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