Antibacterial Activity of Some 3-(Arylideneamino)-2-phenylquinazoline-4(3H)-ones: Synthesis and Preliminary QSAR Studies

Abstract

Synthesis of ten 3-(arylideneamino)-2-phenylquinazoline-4(3H)-ones is reported. All the compounds contained a common phenyl group at the 2-position, while the substituents on the arylideneamino group were varied. The compounds were investigated for their antimicrobial activity against both Gram-positive (Staphylococcus aureus 6571 and Bacillus subtilis) and Gram-negative bacteria (Escherichia coli K12 and Shigella dysenteriae 6) using a turbidometric assay method. It was found that the incorporation of the 3-arylideneamino substituent enhanced the anti-bacterial activity of the quinazolone system. The preliminary QSAR studies were done using some computer derived property descriptors, calculated values of partition coefficients as well as usual Hammett's sigma constants and the substituent's molar refractivity.

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

“…Br C6H5 Benziimidazolyl 8p Br C3H7 Benziimidazolyl Some 3-(arylideneamino)-2-phenylquinazoline-4(3H)-ones derivatives (9a-k) exhibited antibacterial activity [24].…”

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“…On standing for 1 h, solidification occur, the product was filtered off, washed with water and dried. (6)(7)(8)(9)(10)(11)(12)(13)(14): To a solution of the appropriate acetophenones (0.01mol) dissolved in ethanol (20ml), was added different substituted 3-amino-2-phenylquinazolin-4-one derivative (5a-5c) (0.01mol) and pH of the resultant solution was adjusted to 4.0-4.5 using glacial acetic acid. The resulting mixture was refluxed for 2-3 h. The solid thus obtained was filtered and purified by column chromatographic method using n-hexane/ethyl acetate (75:25) as eluents.…”

“…Quinazolin-4(3H)-one represents a versatile lead molecule for the design of potential bioactive agents [1][2][3][4][5][6][7] and the pharmaceuticals containing quinazolinone nucleus show varied biological activities as different substitution patterns results in diverse biological properties [8][9][10] . Number of quinazoline derivatives with different substitutions at 2,3,4,6 positions have been reported and studied as antitumor 11 , antibacterial 12 , anticonvulsant 13 , antimalarials 14 and antiviral agents 15 as shown in Table 1.…”

Synthesis, spectro-analytical, computational and biological studies of novel 6-methyl-3-(1-(4-oxo-2-phenylquinazolin-3(4H)-ylimino) ethyl)-2H-pyran-2, 4(3H)-dione and its Co (II), Cu (II) and Hg (II) metal complexes

“…Quinazolinones are the heterocyclic compounds showing broad spectrum of biological significance such as anticancer [1], antitumour [2], antifungal [3,4], antibacterial [5,6], antitubercular [7], antihistaminic [8], antiinflammatory [9], anticonvulsant [10], immunotropic [11], hypolipidemic [12], antiulcer [13], analgesic [14,15] and CNS depressant [16] activities. The compound 3-acetyl-6-methyl-2H-Pyran-2, 4(3H)-dione upon complexation with transition metals exhibited numerous biological applications [17][18][19][20].…”