Lactacystin derivatives

Details Lactacystin derivatives Lactacystin derivatives

1997-11-28

1999-02-09

Powers, Fiona T.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548530, 548534, C07D20712, C07D40112

Patent

active

058696750

ABSTRACT:
Novel lactacystin derivatives other than lactacystin per se, with superior activity for the genesis of neurites and highly selective toxicity and low cytotoxicity as compared with known lactacystin have been prepared, of the formula ##STR1## wherein R is lower alkoxy, --S--(CH.sub.2).sub.n R.sup.1 or --S--(CH.sub.2) .sub.n --CH(R.sup.2)-(R.sup.3), in which R.sup.1 is branched or straight-chain lower alkyl, hydroxy, carboxyl, lower alkoxycarbonyl, optionally substituted phenyl, substituted or unsubstituted amino or pyridyl, R.sup.2 is substituted or unsubstituted amino, lower alkyl or amino acid residue, R.sup.3 is carboxyl, lower alkoxycarbonyl, lower alkenyloxycarbonyl or amino acid residue, and n is 0-4, or a pharmacologically acceptable salt thereof.

REFERENCES:
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Corey et al., Synthesis of (6R, 7S)-Lactacystin and 6-Deoxylactacystin from a Common Intermediate, Tetrahedron Letters, vol. 34, No. 44, 1993, pp. 6973-6976.
Corey et al., "Studies of the Total Synthesis of Lactacystin, and Improved Aldol Coupling Reaction and a .beta.-Lactone Intermediate in Thiol Ester Formation", Tetrahedron Letters, vol. 34, No. 44, 1993, pp. 6977-6980.
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