255903-84-5Relevant articles and documents
Synthesis of L-4,4-difluoroglutamic acid via electrophilic difluorination of a lactam.
Konas,Coward
, p. 2105 - 2107 (1999)
[formula: see text] An enantiomerically pure bicyclic lactam proved to be an excellent substrate for electrophilic difluorination using N-fluorobenzenesulfonimide. The resulting difluorinated lactam can be easily converted into L-4,4-difluoroglutamic acid. To the best of our knowledge, this is the first example of a synthetically useful electrophilic difluorination of an unactivated lactam.
Synthesis, evaluation of anti-HIV-1 and anti-HCV activity of novel 2′,3′-dideoxy-2′,2′-difluoro-4′-azanucleosides
Martínez-Montero, Saúl,Fernández, Susana,Sanghvi, Yogesh S.,Theodorakis, Emmanuel A.,Detorio, Mervi A.,McBrayer, Tamara R.,Whitaker, Tony,Schinazi, Raymond F.,Gotor, Vicente,Ferrero, Miguel
, p. 6885 - 6893 (2013/01/15)
A series of 2′,3′-dideoxy-2′,2′-difluoro-4′- azanucleosides of both pyrimidine and purine nucleobases were synthesized in an efficient manner starting from commercially available L-pyroglutamic acid via glycosylation of difluorinated pyrrolidine derivative 15. Several 4′-azanucleosides were prepared as a separable mixture of α- and β-anomers. The 6-chloropurine analogue was obtained as a mixture of N 7 and N9 regioisomers and their structures were identified based on NOESY and HMBC spectral data. Among the 4′-azanucleosides tested as HIV-1 inhibitors in primary human lymphocytes, four compounds showed modest activity and the 5-fluorouracil analogue (18d) was found to be the most active compound (EC50 = 36.9 μM) in this series. None of the compounds synthesized in this study demonstrated anti-HCV activity.
