title: Synthesis of AZA analogues of TSAO.
abstract: TSAO derivatives which were first synthesized in 1992 have shown strong inhibitory effect and selectivity against HIV-1 (Camarasa, M.J.; Pérez-Pérez, M.J.; San-Félix, A.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1992, 35, 2721-2727). The structure-activity relationship of these derivatives has shown strong binding between the amino acids constituting the reverse transcriptase and the different pharmacophore (tert-butyldimethylsilyl group, amino and sulfonate groups of the TSAO derivatives) (Camarasa, M.J.; San-Félix, A.; Pérez-Pérez, M.J.; Velázquez, S., Alvarez, R.; Chamorro, C.; Jimeno, M.L.; Pérez, C.; Gago, F.; De Clercq, E.; Balzarini, J. J. Carbohydr. Chem. 2000, 19, 6403-6406). We described the synthesis of an original TSAO analogue where, basically, the O-1'' atom is replaced by a nitrogen atom.
authors.affiliation: Laboratoire des Glucides, Université de Picardie-Jules Verne, Amiens, France.
authors.forename: Albert
authors.initials: A
authors.lastname: Nguyen Van Nhien
authors.forename: Cyrille
authors.initials: C
authors.lastname: Tomassi
authors.forename: Christophe
authors.initials: C
authors.lastname: Len
authors.forename: José Luis
authors.initials: JL
authors.lastname: Marco-Contelles
authors.forename: Denis
authors.initials: D
authors.lastname: Postel
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D019380:Anti-HIV Agents; D001372:Aza Compounds; D013141:Spiro Compounds