Synthesis, Characterization and Antimicrobial Activity of New 2-Phenylquinoline-4(3H)-one Derivatives
نویسنده
چکیده
Quinazolinones is an important chemical synthesis with different physiological significance and pharmacological utility. Reaction of anthranilic acid with benzoyl chloride in pyridine yielded 2-phenyl4H-benzo[d][1,3]oxazin-4-one, which on condensation reaction with the tryptophan in glacial acetic acid afforded 3-(1H-indol-3-yl)-2-(4-oxo-2-phenylquinazolin-3(4H)-yl) propanoic acid (2). Treatment of compound (2) with thionyl chloride produced 3-(1H-indol-3-yl)-2-(4-oxo-2-phenylquinazolin-3(4H)-yl) propanoyl chloride (3).Condensation of compound (3) with hydrazine hydrate gave 3-(1H-indol-3-yl)2-(4-oxo-2-phenylquinazolin-3(4H)-yl) propanehydrazide (4). Condensation of compound (4) with ethyl aceto acetate in glacial acetic acid yielded 3-(3-(1H-indol-3-yl)-1-(3-methyl-5-oxo-4,5-dihydro-1Hpyrazol-1-yl)-1-oxopropan-2-yl)-2-phenylquinazolin-4(3H)-one (5). The reaction of compound (4) with carbon disulfide and sodium hydroxide yielded3-(2-(1H-indol-3-yl)-1-(5-mercapto-1,3,4-oxadiazol-2yl) ethyl)-2-phenylquinazolin-4(3H)-one (6).Condensation of compound (6) with hydrazine hydrate afforded 2-hydrazinyl-5(2-(1H-indol-3-yl) ethyl)-2-phenylquinazolin-4(3H)-one(7). Compound (8) 2-(3-(1H-indol-3-yl)-2-(4-oxo-2-phenylquinazolin-3(4H)-yl)propanoyl)-2,3-dihydrophthalazine-1,4dione was synthesized by condensing compound (4) with phthalic anhydride in glacial acetic acid. When compound (4) was reacted with different aromatic aldehydes in abs. ethanol afforded different substituted (9a-d).Moreover, N-(1,5-dioxo-3-substituted-1,5-dihydrobenzo[e][1,3] oxazepin-4(3H)yl)-3-(1H-indol-3-yl)-2-(4-oxo-2-phenylquinazolin-3(4H)-yl) propanamide (10a,b) were prepared from the cyclic condensation of Schiff bases compounds with phthalic anhydride. The structures of newly synthesized compounds were characterized by m.p., TLC, FTIR and 1H, 13C-NMR spectral analysis. The antimicrobial activity of the synthesized phenylquinazoline on two kinds of bacteria namely, staphylococcus aureous and Escherichia coli was investigated. keywords: Phenylquinazoline, oxadiazole, triazole, pyrazole, oxazepin
منابع مشابه
Synthesis and study of antimicrobial agent 3 - ( 3 - substituted - 1 H - indon - 1 - yl ) - 2 - phenylquinoline - 4 - carboxylic acid
Present work describes the Synthesis of 3-(3-substituted-1H-indon-1-yl)-2-phenylquinoline-4carboxylic acid derivatives by Pfitzinger reaction of isatin with 2(1H-indol-1-yl)-1-phenyl ethanone and 1-phenyl-2-[-3-(substituted)-1-H-indole-1-yl] ethanone. The structures of all the compounds are established by elemental analysis, IR, H NMR and Mass spectral data. These compounds possess excellent an...
متن کاملThiamine hydrochloride (vitamin B1) as an efficient catalyst for the synthesis of 4-(3H)-Quinazolinone derivatives using grinding method.
Herein we explore facile synthesis of 4-(3H)-Qunazolinone derivatives, achieved by the cyclocondensation of anthranilic acid, aromatic amines and triethyl orthoformate in presence of thiamine hydrochloride (Vitamin B1) as a catalyst, using grinding method. This protocol offers several advantages such as reusability of catalyst, excellent yield, shorter reaction time and economic availability.Qu...
متن کاملThiamine hydrochloride (vitamin B1) as an efficient catalyst for the synthesis of 4-(3H)-Quinazolinone derivatives using grinding method.
Herein we explore facile synthesis of 4-(3H)-Qunazolinone derivatives, achieved by the cyclocondensation of anthranilic acid, aromatic amines and triethyl orthoformate in presence of thiamine hydrochloride (Vitamin B1) as a catalyst, using grinding method. This protocol offers several advantages such as reusability of catalyst, excellent yield, shorter reaction time and economic availability.Qu...
متن کاملNew Benzimidazoles Derivatives: Synthesis, Characterization and Antifungal Activities
One of the most important goals in medicinal chemistry is the development of new heterocyclic compounds with pharmaceutical activity. Thus, a novel series of the derivatives of benzimidazole were synthesized and the structures of all the synthesized compounds have been confirmed by IR, 1 H- and 13C-NMR, Mass Spectroscopy and elemental analysis. The title compounds have been evaluated for antifu...
متن کاملSynthesis and Antimicrobial Activity of Some New Isatin Derivatives
Some new 3-[(5-benzylidene-2-phenyl)-3, 5-dihydro-4-H-imidazol-4-one-3-(4-bezoylhydrazono)]-indole-2-ones (VIII) have been synthesized from different isatinhydrazones (II) by condensing with 2-phenyl-5-benzylidene- 3-N (4-acetyl phenyl)-1, 5-dihydro-imidazol-4-one (VII). Their chemical structures have been confirmed by IR, 1HNMR, MASS and by elemental analysis. Investigation of antimicrobial ac...
متن کامل