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Combination Of Bioactive Moieties With Different Heteroatom(s): Application Of The Suzuki Cross‐coupling Reaction

Rahul V Patel, Jigar K. Patel, Premlata Kumari, Kishor H. Chikhalia
Published 2012 · Chemistry

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Two series of thiophene/benzothiophene-linked quinolinyl oxadiazoles condensed to the substituted N-benzothiazolyl acetamides have been synthesized via the Suzuki cross-coupling reaction. The ester derivative of 6-bromo-substituted quinoline was reacted via the Suzuki cross-coupling reaction with commercially available (benzo)thiophen-2-ylboronic acid at optimized temperature in 1,2-dimethoxy ethane and water in the presence of potassium carbonate and palladium tetrakis. The resulting derivatives were then hydrazinolized using 99% hydrazine hydrate followed by cyclization using carbon disulfide in ethanolic KOH to furnish the corresponding oxadiazoles, which were then condensed with various substituted 2-chloro-N-benzothiazolyl acetamides to produce the final scaffolds involving a unique combination of four heterocycles to be examined for their antimicrobial activity against two Gram-positive bacteria (Staphylococcus aureus and Bacillus cereus), three Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumoniae), and two fungal species (Aspergillus niger and Candida albicans). The investigation of biological screening data revealed that the majority of the compounds tested have demonstrated excellent activity (minimum inhibitory concentrations; 6.25–50 µg/mL) against most of the microorganisms as compared with the standard and hence they warrant more consideration as prospective antimicrobial agents. New products (9a–10i) were characterized by physicochemical, elemental, and spectral (IR, 1H NMR, and 13C NMR) data. © 2012 Wiley Periodicals, Inc. Heteroatom Chem 23:399–410, 2012; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.21027
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