title: exo-Imino to endo-iminocyclitol rearrangement. A general route to five-membered antiviral azasugars.
abstract: A facile synthesis is reported for five-membered iminocyclitols which allows for variation in stereochemistry at all the chiral centers, diverse C1- and N-substitution, and the potential for a three-component combinatorial process. The key step is inversion at the C4 stereocenter (L-lyxo sugar --> D-ribono azasugar). The exo-imino to endo-iminocyclitol process was extended to the D-lyxo and the D- and L-hexose series. Some analogues were found to be more potent than N-butyl DNJ and N-nonyl DNJ in antiviral activity.
authors.affiliation: University of Illinois at Chicago, Department of Chemistry, Chicago, Illinois 60607, USA. moriarty@uic.edu
authors.forename: Robert M
authors.initials: RM
authors.lastname: Moriarty
authors.forename: Carmen I
authors.initials: CI
authors.lastname: Mitan
authors.forename: Norica
authors.initials: N
authors.lastname: Branza-Nichita
authors.forename: Kenneth R
authors.initials: KR
authors.lastname: Phares
authors.forename: Damon
authors.initials: D
authors.lastname: Parrish
mesh_terms: D017485:1-Deoxynojirimycin / Q000737:chemistry / Q000494:pharmacology*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D050113:Imino Furanoses / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000998:Antiviral Agents; D001372:Aza Compounds; D050113:Imino Furanoses; D017485:1-Deoxynojirimycin