MS and NMR investigation of bioactive quinazolones

Szabó, Zoltán; Ősz, Erzsébet; Lóránd, Tamás

doi:10.1016/j.jbbm.2004.04.005

Cited by 4 publications

(1 citation statement)

References 9 publications

(10 reference statements)

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“…Reaction of 1 with various alkylating agents like dimethyl sulphate, diethyl sulphate and benzyl chloride (PhCH2Cl) in the presence of K2CO3 as a mild base, by a simple physical grinding of the reaction mixture in a mortar and pestle under solvent-free conditions for 10-15 min at room temperature, followed by processing, gave respectively 2-methylsulfanyl-3H-quinazolin-4-one (2a, i.e., R = CH3), 2-ethylsulfanyl-3Hquinazolin-4-one (2b, i.e., R = C2H5) and 2-benzyl sulfanyl-3H-quinazolin-4-one (2c, i.e., R = PhCH2Cl), as the products identical with the one reported in the earlier methods [17][18][19] in all respects (m.p. m.m.p and co-tlc analysis).…”

Section: Resultssupporting

confidence: 67%

A Green and Facile Synthesis of 2-Alkylsulfanyl-3H-quinazolin-4-one

Reddy¹,

Naidu²,

Dubey³

2013

Asian J. Chem.

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The quinazolinone ring system forms an important class of N-heterocyclic compounds as it is present in a large number of compounds with useful biological properties such as antiinflammatory 1,2 , anticonvulsant 3 , hypotensive 4 and antimalarial 5 types. 2-Thioquinazolinones possess good analgesic activities 6 . 2-Substituted quinazolin-4(3H)-ones exhibit a wide range of pharmacological properties 7,8 , such as good antimicrobial activity against different species of gram positive bacteria 9 , gram-negative bacteria 10 , pathogenic fungi 11,12 , antitubercular activity 13,14 and antitumor chemotherapeutic agent 15,16 . EXPERIMENTALAll the reagents used in this work were obtained from commercial suppliers. Solvents were freshly distilled before being used. Melting points were determined using a Buchi melting point B-545 apparatus and are uncorrected. TLC analyses were done on glass plates coated with silica gel GF-254 and spotting was done using iodine/UV lamp. IR spectra were recorded on a Perkin-Elmer model 446 instrument in KBr phase. 1 H NMR were recorded in CDCl3/DMSO using 400 MHz Varian Gemini spectrometer and mass spectra were recorded on a LC-MS spectrometer, model HP-5989A. Experiments under microwave irradiation were carried out by using the commercially available CEM discover microwave reactor. Elemental analyses were performed by Varian 3LV analyzer series CHN analyzer.Reaction of 2-thioquinazolinone (1) with various alkylating agents like dimethyl sulphate, diethyl sulphate and benzyl chloride in the presence of K2CO3 as a mild base, by a simple physical grinding, microwave irradiation and PEG-600 under solvent-free conditions for 10-15 min at room temperature, followed by processing, gave respectively 2-methylsulfanyl-3H-quinazolin-4-one (2a, i.e., R = CH3), 2-ethylsulfanyl-3H-quinazolin-4-one (2b, i.e., R = C2H5) and 2-benzyl sulfanyl-3H-quinazolin-4-one (2c, i.e., R = PhCH2Cl). It appears from this study that green syntheses such as solid phase synthesis (physical grinding) and microwave irradiation gives better yields, quality and in less reaction time the products over conventional methods involving green solvents like ethanol, PEG-600 etc. The entire sequences of reactions have been carried out using eco-friendly solvents and green conditions.

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Section: Resultssupporting

confidence: 67%

A Green and Facile Synthesis of 2-Alkylsulfanyl-3H-quinazolin-4-one

Reddy¹,

Naidu²,

Dubey³

2013

Asian J. Chem.

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Copper‐Mediated Direct and Selective C−H Thiolation of Quinazolinones

et al. 2019

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Current literature in mass spectrometry

2005

J. Mass Spectrom.

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In order to keep subscribers up‐to‐date with the latest developments in their field, John Wiley & Sons are providing a current awareness service in each issue of the journal. The bibliography contains newly published material in the field of mass spectrometry. Each bibliography is divided into 11 sections: 1 Books, Reviews & Symposia; 2 Instrumental Techniques & Methods; 3 Gas Phase Ion Chemistry; 4 Biology/Biochemistry: Amino Acids, Peptides & Proteins; Carbohydrates; Lipids; Nucleic Acids; 5 Pharmacology/Toxicology; 6 Natural Products; 7 Analysis of Organic Compounds; 8 Analysis of Inorganics/Organometallics; 9 Surface Analysis; 10 Environmental Analysis; 11 Elemental Analysis. Within each section, articles are listed in alphabetical order with respect to author (4 Weeks journals ‐ Search completed at 8th. June 2005)

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MS and NMR investigation of bioactive quinazolones

Cited by 4 publications

References 9 publications

A Green and Facile Synthesis of 2-Alkylsulfanyl-3H-quinazolin-4-one

A Green and Facile Synthesis of 2-Alkylsulfanyl-3H-quinazolin-4-one

Copper‐Mediated Direct and Selective C−H Thiolation of Quinazolinones

Current literature in mass spectrometry

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