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. 2016 Apr 13;84(3):484-496.
doi: 10.3390/scipharm84030484.

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

Khalid A Agha  1 , Nader E Abo-Dya  2   3 , Tarek S Ibrahim  4 , Eatedal H Abdel-Aal  5 , Wael A Hegazy  6
Affiliations

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

Khalid A Agha et al. Sci Pharm. .

Abstract

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).

Keywords: acylation; antibiotics; benzotriazolides; drug research.

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Conflict of interest statement

The authors have no conflicts of interest.

Figures

Figure 1
Figure 1
Cephalexin.
Scheme 1
Scheme 1
Synthesis of 4-methyl-2-(3,4,5-trimethoxybenzamido)thiazole-5-carboxylic acid (2j).
Scheme 2
Scheme 2
Synthesis of target compounds N-acylcephalexins (4a–k′).
Figure 2
Figure 2
Inhibition measured in mm.
See this image and copyright information in PMC

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