exo-Imino to endo-iminocyclitol rearrangement. A general route to five-membered antiviral azasugars.
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.
Moriarty
Robert M
RM
University of Illinois at Chicago, Department of Chemistry, Chicago, Illinois 60607, USA. moriarty@uic.edu
Mitan
Carmen I
CI
Branza-Nichita
Norica
N
Phares
Kenneth R
KR
Parrish
Damon
D
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
D000998:Antiviral Agents; D001372:Aza Compounds; D050113:Imino Furanoses; D017485:1-Deoxynojirimycin