Literature

Abstract

A series of novel heterocyclic taxol analogues has been synthesized utilizing 2-azetidinones derived from the ester enolate-imine cyclocondensation. 2-Azetidinones possessing stereochemistry complementary to that of taxol's phenylisoserine side chain were synthesized in fair to high enantiomeric purity utilizing the chiral glycolate derived from Oppolzer's chiral auxiliary and the appropriate Ntrimethylsilylaldimines. These novel analogues were evaluated in the microtubule assembly assay as well as tested for cytotoxicity against B16 melanoma cells. The 2-furyl analogue 29 proved to be more active than the parent, taxol.

DOI： 10.1016/S0960-894X(01)80366-8

Heteroaromatic Taxol Analogues: The Chemistry and Biological Activities of 3′-Furyl and 3′-Pyridyl Substituted Taxanes

Bioorganic & Medicinal Chemistry Letters 1994.0

Synthesis of biologically active taxol analogs with modified phenylisoserine side chains

Journal of Medicinal Chemistry 1992.0

Novel Biologically Active Taxol Analogues: Baccatin III 13-(N-(p-chlorobenzoyl)-(2′R,3′S)-3′-phenylisoserinate) and Baccatin III 13-(N-benzoyl-(2′R,3′S)-3′-(p-chlorophenyl)isoserinate)

Bioorganic & Medicinal Chemistry Letters 1992.0

Semisynthesis and biological activity of taxol analogues: baccatin III 13-(N-benzoyl-(2′R,3′S)-3′-(p-tolyl)isoserinate), baccatin III 13-(N-(p-toluoyl)-2′R,3′S)-3′-phenylisoserinate), baccatin III 13-(N-benzoyl-(2′R,3′S)-3′-(p-trifluoromethylphenyl)isoserinate), and baccatin III 13-(N-(p-trifluoromethylbenzoyl)-(2′R,3′S)-3′-phenylisoserinate)

Bioorganic & Medicinal Chemistry Letters 1992.0

Schotten-Baumann acylation of N-debenzoyltaxol; an efficient route to N-acyl taxol analogues and their biological evaluation

Bioorganic & Medicinal Chemistry Letters 1994.0

Biologically active taxol analogs with deleted A-ring side chain substituents and variable C-2' configurations