Synthesis of UDP-glucose:
Disclosed is a novel enantiomeric synthesis ceramide-like inhibitors of UDP-glucose: N-acylsphingosine glucosyltransferase. Also disclosed are novel intermediates formed during the synthesis.
1. A compound represented by the following structural formula:
the enantiomer of the compound, a salt of the compound, or a salt of the enantiomer, wherein:
R 1 is a substituted or unsubstituted aromatic group;
R 2 and R 3 are independently —H, a substituted or unsubstituted aliphatic group or, taken together with the nitrogen atom to which they are bonded, are a substituted or unsubstituted non-aromatic heterocyclic ring;
R 4 is O or H 2 ; and
R 5 is a substituted or unsubstituted aromatic group.
2. The compound of claim 1 wherein:
R 1 and R 5 are independently a substituted or unsubstituted phenyl group; and
R 2 and R 3 are independently —H, an unsubstituted C1-C5 alkyl group or, taken together with the nitrogen atom to which they are bonded, are an unsubstituted C3-C10 non-aromatic heterocyclic ring.
3. The compound of claim 2 wherein R 5 is a phenyl group.
4. The compound of claim 3 wherein R 2 and R 3 taken together with the nitrogen atom to which they are bonded, are pyrrolidinyl, piperazinyl, azetidinyl, morpholinyl, thiomorpholinyl, azacycloheptyl, piperidinyl or N-phenylpiperazinyl.
5. A compound represented by the following structural formula:
the enantiomer of the compound, a salt of the compound, or a salt of the enantiomer, wherein R 1 is a substituted or unsubstituted phenyl group and R 4 is H 2 or O.
6. The compound of claim 5 wherein the phenyl group represented by R 1 is substituted with —OCH 2 O—, —OCH 2 CH 2 O—, halo, —O(lower alkyl), —OH, lower alkyl thiol, —O(phenyl), —OCH 2 (phenyl), —O—CH 2 — (phenyl), lower alkyl, amino, lower alkyl amino or lower dialkyl amino.