Synthesis and photodecomposition of antibiotics containing ethanolamine and oxazolidine moieties.
Abstract
AbstractAntimicrobial resistance is a leading cause of death globally and is on the rise. The discoveryof new antibiotics is declining, and the synthesis of new scaffolds with decomposing propertiesis more important now than ever to combat the rise of antimicrobial resistance. The goal of thisproject was to synthesize photodecomposable antibiotics containing the ethanolamine moiety,and further modify this to the corresponding oxazolidine.1-((2,5-Dichloro-4-nitrophenyl)amino)-3-phenylpropan-2-ol (3a) was successfully synthesizedto a yield of 13%. Compound 3a was used to synthesize 5-benzyl-3-(2,5-dichloro-4-nitrophenyl)oxazolidine (4) in a yield of 31%. Photodecomposition was conducted forcompounds 3a and 4, and they were fully photodecomposed after approximately 24 hours asjudged by 1H NMR. Compounds 3a and 4 have been submitted for biological testing and resultsare expected later this spring. Results from biological testing are therefore not included in thisreport.Attempts were also made to synthesize 1-((2,6-dichloro-4-nitrophenyl)amino)-3-phenylpropan-2-ol (3b) using the appropriate aniline (1b) and (2,3-epoxypropyl)benzene (2).None of the reactions that were attempted were successful. AbstractAntimicrobial resistance is a leading cause of death globally and is on the rise. The discoveryof new antibiotics is declining, and the synthesis of new scaffolds with decomposing propertiesis more important now than ever to combat the rise of antimicrobial resistance. The goal of thisproject was to synthesize photodecomposable antibiotics containing the ethanolamine moiety,and further modify this to the corresponding oxazolidine.1-((2,5-Dichloro-4-nitrophenyl)amino)-3-phenylpropan-2-ol (3a) was successfully synthesizedto a yield of 13%. Compound 3a was used to synthesize 5-benzyl-3-(2,5-dichloro-4-nitrophenyl)oxazolidine (4) in a yield of 31%. Photodecomposition was conducted forcompounds 3a and 4, and they were fully photodecomposed after approximately 24 hours asjudged by 1H NMR. Compounds 3a and 4 have been submitted for biological testing and resultsare expected later this spring. Results from biological testing are therefore not included in thisreport.Attempts were also made to synthesize 1-((2,6-dichloro-4-nitrophenyl)amino)-3-phenylpropan-2-ol (3b) using the appropriate aniline (1b) and (2,3-epoxypropyl)benzene (2).None of the reactions that were attempted were successful.