PDF icon Download PDF
Arzneimittelforschung 2005; 55(2): 107-113
DOI: 10.1055/s-0031-1296831
Antibiotics · Antiviral Drugs · Chemotherapeutics · Cytostatics
Editio Cantor Verlag Aulendorf (Germany)

Synthesis and Evaluation of the Antibacterial and Antitubercular Activity of Some N1-Aral-N4-(3-Chloro-4-fluorophenyl) thiosemicarbazones and their Copper(I) Complexes

Imtiyazahmed M. Khazi
a   Post Graduate Department of Studies in Chemistry, Karnatak University, Dharwad, India
,
Rajesh S. Koti
a   Post Graduate Department of Studies in Chemistry, Karnatak University, Dharwad, India
,
Monica V. Chadha
b   Department of Medicinal Chemistry, College of Pharmacy, Jawaharlal Nehru Medical College, Belgaum, India
,
Channabasappa S. Mahajanshetti
b   Department of Medicinal Chemistry, College of Pharmacy, Jawaharlal Nehru Medical College, Belgaum, India
,
Andanappa K. Gadad
b   Department of Medicinal Chemistry, College of Pharmacy, Jawaharlal Nehru Medical College, Belgaum, India
› Author Affiliations
Further Information

Publication History

Publication Date:
23 December 2011 (online)

 PDF Download  Permissions and Reprints
Preview

Summary

New N1-aral-N4-(3-chloro-4-fluoro-phenyl)thiosemicarbazones (2a-h) and their Cu(I) complexes (3a-h) have been prepared and characterized by elemental analysis and spectral methods (IR and 1H-NMR). Thiosemicarbazones 2a-h bind to copper(I) as bidentate ligand via nitrogen and thione sulphur centers to afford 3a-h. Both ligands and their complexes are screened against Escherichia coli (National Collection of Type Culture 10418) and Staphylococcus aureus (National Collection of Type Culture 5571) to evaluate their antibacterial properties and against human virulent H37Rv strain of Mycobacterium tuberculosis for their antitubercular properties. Ligands 2d-h showed promising antibacterial activity while their Cu(I) complexes 3d-h exhibited excellent activity. The compounds 2a, 2d, 2f, 2g and their Cu(I) complexes 3a, 3d, 3f and 3g were evaluated for their antitubercular activity. It was observed that compounds 2a, 2g, 3a, 3d showed moderate activity while 3f and 3g exhibited promising antitubercular activity.

Zusammenfassung

Synthese und Bewertung der antibakteriellen und antituberkulösen Wirkung von N1-Aral-N4-(3-chloro-4-fluorophenyl) thiosemicarbazonen und ihren Kupfer(I)-Komplexen

Neue N1-Aral-N4-(3-chloro-4-fluoro-phenyl)thiosemicarbazone (2a-h) und ihre Cu(I)-Komplexe (3a-h) wurden synthetisiert und mittels Elementaranalyse sowie spektrometrisch (IR and 1H-NMR) charakterisiert. Die Thiosemicarbazone 2a-h banden an Kupfer(I) als zweifache Liganden via Stickstoff- und Thion-Schwefel-Zentren und ergaben 3a-h.

Beide Liganden sowie ihre Komplexe wurden an Escherichia coli (National Collection of Type Culture 10418) und Staphylo-coccus aureus (National Collection of Type Culture 5571) getestet, um ihre antibakteriellen Eigenschaften zu bewerten, sowie am menschlichen virulenten H37Rv-Stamm von Mycobacterium tuberculosis, um ihre antituberkulöse Wirkung zu untersuchen. Die Liganden 2d-h zeigten vielversprechende antibakterielle Wirkung, während die Wirkung ihrer Cu(I)-Komplexe 3d-h ausgezeichnet war. Die Verbindungen 2a, 2d, 2f, 2g sowie ihre Cu(I)-Komplexe 3a, 3d, 3f und 3g wurden auf antituberkulöse Wirkung geprüft. Dabei waren 2a, 2g, 3a, 3d moderat wirksam, während 3f und 3g vielversprechende antituberkulöse Wirkung zeigten.

Key words

N1-Aral-N4-(3-chloro-4-fluorophenyl) thiosemicarba-zones, antibacterial activity - antitubercular activity, synthesis - Cu(I) complexes of N1-aral-N4- (3-chloro-4-fluorophenyl) - thiosemicarbazones, antibacterial - activity, antitubercular activity, synthesis