title: [Synthesis and biological properties of α-thymidine 5'-aryl phosphonates].
abstract: The interaction of CDI-activated diethyl phosphonoacetate with methyl 4-aminobenzoat or 3,5-difluoromethylphenylamine followed by treatment with Me3SiBr in DMF led to N-aryl aminocarbonylmethyl phosphonates and their ethyl esters. Their coupling with 3'-acetyl-α-thymidine followed by removal of the acetyl groups gave (α-D-thymidine-5'-il) N-[4-(methoxycarbonyl-, aminocarbonyl- and carboxy)phenyl]-aminocarbonylmethyl phosphonates, (α-D-thymidine-5'-il)-[3,5-bis(trifluoromethyl)phenylaminocarbonyl]methyl phosphonate and their ethyl esters. The phosphonates were stable in different conditions, low cytotoxic (in Vero and K562 cells) and were able to penetrate into K562 cells. The only ethyl ester of (α-D-thymidine-5'-il) N-[4-(methoxycarbonyl)phenyl]-aminocarbonylmethyl phosphonate in high concentration (200 μg/mL) inhibited in vitro the growth of laboratory sensitive strain of Mycobacterium tuberculosis H37Rv.
authors.forename: M A
authors.initials: MA
authors.lastname: Ivanov
authors.forename: I L
authors.initials: IL
authors.lastname: Karpenko
authors.forename: L N
authors.initials: LN
authors.lastname: Chernousova
authors.forename: S N
authors.initials: SN
authors.lastname: Andreevskaia
authors.forename: T G
authors.initials: TG
authors.lastname: Smirnova
authors.forename: L A
authors.initials: LA
authors.lastname: Aleksandrova
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D009169:Mycobacterium tuberculosis / Q000187:drug effects* / Q000201:enzymology; D013942:Thymine Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014376:Tuberculosis / Q000188:drug therapy / Q000382:microbiology*
chemical_list: D000890:Anti-Infective Agents; D004791:Enzyme Inhibitors; D013942:Thymine Nucleotides; C119095:thymidine 5'-phosphonate