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Benzotriazole-Mediated Synthesis and Antibacterial Activity of Novel N-Acylcephalexins. 2016

Khalid A Agha, and Nader E Abo-Dya, and Tarek S Ibrahim, and Eatedal H Abdel-Aal, and Wael A Hegazy
Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig 44519, Egypt. aghanet2010@yahoo.com.

Cephalexin (1) was acylated using N-acylbenzotriazoles (3a-k') derived from various carboxylic acids including aromatic, heterocyclic and N-Pg-α-amino acid to afford N-acylcephalexins in excellent yields (82%-96%). Antibacterial screening of the novel cephalosporins revealed that all targets (4a-j) retained the antibacterial activity of cephalexin against Staphylococcus aureus (ATCC 6538). N-Nicotinylcephalexin (4c) and N-(3,4,5-trimethoxybenzoyl)cephalexin (4g) exhibited a broader spectrum of antibacterial activity towards standard strains of Staphylococcus aureus (ATCC 6538), Paenibacillus polymyxa (ATCC 842), and Escherichia coli (ATCC 10536) as well as a resistant strain of Pseudomonas aeruginosa (ATCC 27853).

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