Aminophosphonic Acids and Aminobis(phosphonic acids) as Potential Inhibitors of Penicillin-Binding Proteins
(2009) European Journal of Organic Chemistry — n° 1, p. 85-97 (2009)
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- Abstract
- Aminophosphonic acids and aminobis(phosphonic acids) have been prepared by the alkylation of Schiff bases with methyl bromoacetate or ethyl acrylate. Other pathways, like the modified Pudovik reaction and Kabachnik-Fields reaction, have been considered for the synthesis of the a-phosphonic bioisoster of aminocitrate. Partial or complete deprotection of the phosphonate ester have been realised by either acidic hydrolysis or by treatment with trimethylsilyl bromide. Evaluation against penicillin-binding proteins has shown that our compounds are modest inhibitors of class A beta-lactamases, but have an interesting activity against R39 (D,D-peptidase/carboxypeptidase). ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
- Affiliations
Uliège Ctr Ingn Prot Uliège Ctr Rech Cylotron
Citations
Beck, J., Gharbi, S., Herteg-Fernea, A., Vercheval, L., Bebrone, C., Lassaux, P., Zervosen, A., & Marchand-Brynaert, J. (2009). Aminophosphonic Acids and Aminobis(phosphonic acids) as Potential Inhibitors of Penicillin-Binding Proteins. European Journal of Organic Chemistry, 1, 85-97. https://doi.org/10.1002/ejoc.200800812 (Original work published 2009)