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Synthesis and Characterization of New 3,5-Dinaphthyl Substituted 2-Pyrazolines and Study of Their Antimicrobial Activity
Department of Chemistry, Faculty of Science, Bu-Ali Sina University, Zip Code 65174, Hamadan, Iran
* Author to whom correspondence should be addressed.
Received: 12 March 2002; in revised form: 15 November 2002 / Accepted: 17 November 2002 / Published: 31 December 2002
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.
Keywords: Chalcones; (Naphthalene-/substituted naphthalene-1-yl)-2-pyrazolines; Aryl substituted pyrazolines; Pyrazolines; Antimicrobial activity; Heterocyclics
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MDPI and ACS Style
Azarifar, D.; Shaebanzadeh, M. Synthesis and Characterization of New 3,5-Dinaphthyl Substituted 2-Pyrazolines and Study of Their Antimicrobial Activity. Molecules 2002, 7, 885-895.
Azarifar D, Shaebanzadeh M. Synthesis and Characterization of New 3,5-Dinaphthyl Substituted 2-Pyrazolines and Study of Their Antimicrobial Activity. Molecules. 2002; 7(12):885-895.
Azarifar, Davood; Shaebanzadeh, Maseud. 2002. "Synthesis and Characterization of New 3,5-Dinaphthyl Substituted 2-Pyrazolines and Study of Their Antimicrobial Activity." Molecules 7, no. 12: 885-895.