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

Abstract

Two novel taxol analogues, baccatin III 13-(N-(p-chlorobenzoyl)-(2'R,3'S)-3'-phenylisoserinate) (2) and baccatin III 13-(N-benzoyl-(2'R,3'S)-3'-(p-chlorophenyl)isoserinate) (3) were synthesized from 7-triethylsilyl baccatin III (4) and N-acyl 3-ethoxyethyloxy-4-aryl-2-azetidinones 5 and 6 in two steps and excellent overall yield. Both derivatives demonstrated activity in the microtubule assembly assay and cytotoxicity against B16 melanoma cells comparable to taxol.

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