Synthesis and biological evaluation of α-hydroxyalkylphosphonates as new antimicrobial agents

Ana Maria Madeira Martins Faísca Phillips; Maria Teresa Barros; Marta Pacheco; Ricardo J. Dias

doi:10.1016/j.bmcl.2013.12.002

Synthesis and biological evaluation of α-hydroxyalkylphosphonates as new antimicrobial agents

Ana Maria Madeira Martins Faísca Phillips, Maria Teresa Barros, Marta Pacheco, Ricardo J. Dias

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

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.

Original language	English
Pages (from-to)	49-53
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	24
Issue number	1
DOIs	https://doi.org/10.1016/j.bmcl.2013.12.002
Publication status	Published - 1 Jan 2014

Keywords

Antimicrobial activity
Clinical isolates
Gram-negative
Gram-positive
Phosphonates

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10.1016/j.bmcl.2013.12.002

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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.",

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AU - Barros, Maria Teresa

AU - Pacheco, Marta

AU - Dias, Ricardo J.

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AB - 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.

KW - Antimicrobial activity

KW - Clinical isolates

KW - Gram-negative

KW - Gram-positive

KW - Phosphonates

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JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

SN - 0960-894X

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ER -

Synthesis and biological evaluation of α-hydroxyalkylphosphonates as new antimicrobial agents

Abstract

Keywords

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