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)

Artigo Revisado por pares

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)

1992; Elsevier BV; Volume: 2; Issue: 4 Linguagem: Inglês

10.1016/s0960-894x(01)80203-1

ISSN

1464-3405

Autores

Gunda I. Georg, Zacharia S. Cheruvallath, Richard H. Himes, Magdalena R. Mejillano,

Tópico(s)

Synthetic Organic Chemistry Methods

Resumo

Two novel taxol analogues, baccatin III 13-(N-(p-chlorobenzoyl)-(2′R,3′S)-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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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)