title: Synthesis and biological evaluation of α-hydroxyalkylphosphonates as new antimicrobial agents.
abstract: A set of α-quaternary 3-chloro-1-hydroxyalkylphosphonates, analogues of fosfomycin and fosfonochlorin, some of which are new compounds, was synthesized. The compounds were screened for bioactivity against several clinical and standard microbial isolates. Some were found to have moderate activity. The activity was higher with phenyl protection of the phosphoryl ester groups and α-phenyl substitution. Compound 11 was as effective or more potent than fosfomycin or chloramphenicol against several Gram-negative bacteria as well as against some Gram-positive ones.
authors.affiliation: Department of Chemistry, CQFB-REQUIMTE, Faculty of Sciences and Technology, Universidade Nova de Lisboa, Campus de Caparica, Quinta da Torre, 2829-516 Caparica, Portugal. Electronic address: amfp@fct.unl.pt.
authors.forename: Ana Maria
authors.initials: AM
authors.lastname: Faísca Phillips
authors.affiliation: Department of Chemistry, CQFB-REQUIMTE, Faculty of Sciences and Technology, Universidade Nova de Lisboa, Campus de Caparica, Quinta da Torre, 2829-516 Caparica, Portugal. Electronic address: mtb@fct.unl.pt.
authors.forename: Maria Teresa
authors.initials: MT
authors.lastname: Barros
authors.affiliation: Microbiology and Biotechnology Laboratory, Center for Biodiversity, Functional and Integrative Genomics, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, Portugal.
authors.forename: Marta
authors.initials: M
authors.lastname: Pacheco
authors.affiliation: Microbiology and Biotechnology Laboratory, Center for Biodiversity, Functional and Integrative Genomics, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, Portugal.
authors.forename: Ricardo
authors.initials: R
authors.lastname: Dias
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D006090:Gram-Negative Bacteria / Q000187:drug effects*; D006094:Gram-Positive Bacteria / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D063065:Organophosphonates
keywords: Antimicrobial activity; Clinical isolates; Gram-negative; Gram-positive; Phosphonates