Novel alpha-aminophosphonic acids. Design, characterization, and biological activity.
Novel alpha-aminophosphonic acids are synthesized reacting 1,3-oxazolidin-2-one derivatives with formaldehyde and phosphorus trichloride. Treatment of N-(phosphonomethyl)oxazolidinones with aqueous NaOH gave the expected alpha-aminophosphonic acids. The oxidation of (2-hydroxy-1,1-dimethylethylamino)methyl phosphonic acid in the presence of CdO and water resulted in N-phosphonomethyl-2-methyl-1-propanoic acid. Their structures were proved by means of IR, 1H, 13C, and 31P NMR spectroscopy. The genotoxic, clastogenic, and antiproliferative effects of newly synthesized original aminophosphonic acids were investigated for the first time.
Naydenova
Emilia
E
University of Chemical Technology and Metallurgy, Department of Organic Chemistry, Sofia 1756, Bulgaria.
Topashka-Ancheva
Margarita
M
Todorov
Petar
P
Yordanova
Ts
Ts
Troev
Kolio
K
D000818:Animals; D001854:Bone Marrow Cells / Q000187:drug effects; D049109:Cell Proliferation / Q000187:drug effects; D002869:Chromosome Aberrations / Q000187:drug effects; D020732:Cytogenetic Analysis / Q000379:methods; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D051379:Mice; D008810:Mice, Inbred C57BL; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D063065:Organophosphonates