Conventional and Microwave Assisted Synthesis of 3-(Substituted)-2-phenyl quinazolin-4(3H)-one and their Antibacterial and Anthelmintic Activity

DOI:

https://doi.org/10.37285/ijpsn.2011.4.2.6

Authors

  • Subal Debnath
  • S Y Manjunath

Abstract

 The present research work was aimed to synthesize a series of various substituted quinazolinone containing 3-(substituted)-2-phenylquinazolin-4(3H)-one.  The compound 3-[(2-oxo-4-phenylazetidin-1-yl)-carbonyl]-2-phenylquinazolin-4(3H)-one, II was prepared by treating 4-oxo-2-phenyl-N-[(E)-phenylmethylidene]quinazoline-3(4H)-carboxamide, I with acetyl chloride and triethylamine (TEA) in benzene by conventional and microwave irradiation method. Synthesis of 3-[{2-oxo-3-(2,4-dichlorophenoxy)-4-phenylazetidin-carbonyl]-2-phenylquinazolin-4(3H)-one, III was carried out by reacting, I with 2,4-dichlorophenoxyacetic acid and thionyl chloride in benzene. The compound 2-phenyl-3-(5-phenyl-1H-1,2,4-triazol-3-yl)quinazolin-4(3H)-one, IV was obtained by reacting I with hydrazine hydrate in ethanol. Synthesis of 2-phenyl-3-(5-phenyl-1,2,4-oxadiazol-3-yl)-quinazolin-4(3H)-one, V was done by reacting I with hydroxylamine hydrochloride in ethanol. These derivatives were prepared by microwave as well as the conventional method. Structure of the compounds has been established by means of IR, 1H-NMR and MS. All the compounds were evaluated for antibacterial activity against Gram-positive bacteria like Staphylococcus aureus, Bacillus subtilis and Gram-negative bacteria like Pseudomonas aeroginosa, Escherichia coli. Most of the compounds showed significant antibacterial activities when compared with the standard drug ciprofloxacin at the concentration of 500 µg/ml and 250 µg/ml.  In this research work, in vitro anthelmintic activity of 3-(substituted)-2-phenylquinazolin-4(3H)-one carried out in comparison with piperazine citrate. These newly synthesized quinazolinone derivatives showed paralysis and were followed by death at concentrations of 10 mg/ml for the screening of the anthelmintic activity.

 

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Keywords:

Quinazolin-4(3H)-one, azetidinone, triazole, oxadiazole

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Published

2011-08-31

How to Cite

1.
Debnath S, Manjunath SY. Conventional and Microwave Assisted Synthesis of 3-(Substituted)-2-phenyl quinazolin-4(3H)-one and their Antibacterial and Anthelmintic Activity. Scopus Indexed [Internet]. 2011 Aug. 31 [cited 2024 Jun. 20];4(2):1408-11. Available from: http://www.ijpsnonline.com/index.php/ijpsn/article/view/426

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Section

Research Articles

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