Synthesis of 2-aziridinyl phosphonates by modified Gabriel–Cromwell reaction and their antibacterial activities

• Published in: European journal of medicinal chemistry 2011-06, Vol.46 (6), p.2485-2489
• Main Authors: Doğan, Özdemir, Babiz, Hakan, Gözen, Ayşe Gül, Budak, Songül
• Format: Article
• Language: English
• Subjects: Ampicillin - pharmacology; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial activity; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Aziridines - chemical synthesis; Aziridines - chemistry; Aziridines - pharmacology; Aziridinyl phosphonates; Bacteria - drug effects; Bacteria - growth & development; Biological and medical sciences; Medical sciences; Microbial Sensitivity Tests; Molecular Structure; Organophosphonates - chemical synthesis; Organophosphonates - chemistry; Organophosphonates - pharmacology; Pharmacology. Drug treatments; Stereoisomerism; Streptomycin - pharmacology; Structure-Activity Relationship
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2011.03.037

A set of new aziridinyl phosphonates (4a–g) were synthesized by using the Gabriel–Cromwell reaction and its modified version developed in this study and their structures confirmed by HRMS, IR, and NMR spectra. All the compounds were screened for their antibacterial activity. They all showed comparable moderate to good growth inhibitory activity in reference to ampicillin and streptomycin. New 2-aziridinyl phosphonates were synthesized by the modified Gabriel–Cromwell reaction and their antibacterial activity were measured. [Display omitted] ► A new method for the synthesis of 2-aziridinyl phosphonates was developed. ► Using this method eight new aziridinyl phosphonates were synthesized in 70–92% yield. ► The antibacterial activities of synthesized compounds were tested for the first time. ► Their activity is in borderline with respect to the reference antibiotics.