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Synthesis and Characterization of New 3,5-Dinaphthyl Substituted 2-Pyrazolines and Study of Their Antimicrobial Activity

Author(s): Davood Azarifar | Maseud Shaebanzadeh

Journal: Molecules ISSN 1420-3049
Volume: 7; Issue: 12; Start page: 885; Date: 2002;
Original page

Keywords: Chalcones | (Naphthalene-/substituted naphthalene-1-yl)-2-pyrazolines | Aryl substituted pyrazolines | Pyrazolines | Antimicrobial activity | Heterocyclics

ABSTRACT
A number of chalcones were prepared by condensing either 1-acetylnaphthalene or substituted 1-acetylnaphthalenes with 1-naphthaldehyde or 4-dimethylamino-1-naphthaldehyde in ethanolic NaOH solutions. These chalcones were immediately reacted with hydrazine hydrochloride, phenyl hydrazine and semicarbazide hydrochloride in the presence of dry acetic acid to obtain the corresponding 2-pyrazolines. The synthesised heterocycles were characterized on the basis of their chemical properties and spectroscopic data. These compounds were tested for antimicrobial activity against a variety of test organisms: Escherichia coli, Staphylococcus aureus, Klebsiella pneumoniae, Proteus mirabillis, Shigella dysentry and Salmonella typhii. The compounds containing chloro, hydroxo and dimethylamino - N(CH3)2 group as substituents on the naphthalene rings have been found to be very effective antimicrobial agents. In addition, the presence of a carboxamido -CONH2 substituent group at the N-1 position of the 2-pyrazoline rings is shown to contribute substantially to the antimicrobial activity.