General Papers ARKIVOC 2009 (xiv) 64-74
An efficient one-pot synthesis and in vitro antimicrobial activity of new pyridine derivatives bearing the tetrazoloquinoline nucleus
Divyesh C. Mungra, Manish P. Patel, and Ranjan G. Patel*
Department of Chemistry, S. P. University, Vallabh Vidyanagar-388 120, Gujarat, India E-mail: patelranjanben@yahoo.com
Abstract
A new series of 2-amino-3-cyano-4-tetrazoloquinolinylpyridine derivatives has been synthesized by the one-pot cyclocondensation reaction of a tetrazolo[1,5-a]quinoline-4-carbaldehyde, malononitrile, a heterocyclic/aromatic methyl ketone and ammonium acetate. All the synthesized compounds were subjected to in vitro antimicrobial screening against a panel of pathogenic strains of bacteria and fungi. Some of the compounds were found to be equipotent or more potent than commercial antibiotics as evident from the results.
Keywords: 2-Amino-3-cyano-4-tetrazoloquinolinylpyridine, tetrazolo[1,5-a]quinoline-4carbaldehyde, one-pot synthesis, antimicrobial activity, MIC
Introduction
Many naturally occurring and synthetic compounds bearing pyridine scaffold possess interesting biological properties.1 In association with those, 2-amino-3-cyanopyridine derivatives have been identified as IKK-ß inhibitors2 along with its importance and utility as intermediates in preparing variety of heterocyclic compounds.3 Consequently, the synthesis of 2-amino-3-cyanopyridine derivatives keeps on attracting much interest in organic chemistry. Various routes for the synthesis of 2-amino-3-cyanopyridine derivatives have been reported using two-component as well as three-component reactions.4-7 Tu and coworkers have reported a facile synthesis of 2amino- 3-cyanopyridine derivatives in a one-pot reaction using aromatic aldehyde, methyl ketone, malononitrile and ammonium acetate.4 A literature survey shows that a number of pyridine derivatives have been synthesized using various aldehydes but not a single reference have been found where tetrazolo[1,5-a]quinoline-4-carbaldehyde is used. We wish to report herein this heterocyclic aldehyde which is biologically active8-10 with a view to obtaining more active heterocyclic system containing two biologically active moieties quinoline11-13 and pyridine14,15 together. The most suitable protocol for the synthesis of functionalized organic compounds would be a one-pot reaction due to the fact that the synthesis can be performed without the
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