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 )

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

doi:10.1016/S0960-894X(01)80203-1

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 )

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

Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

28 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	295-298
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	2
Issue number	4
DOIs	https://doi.org/10.1016/S0960-894X(01)80203-1
State	Published - 1992

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SDG 3 Good Health and Well-being

Keywords

Taxol analogues
cytotoxicity
microtubule assembly
synthesis
β-lactams

Publisher link

10.1016/S0960-894X(01)80203-1

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Georg, G. I., Cheruvallath, Z. S., Himes, R. H., & Mejillano, M. R. (1992). 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 and Medicinal Chemistry Letters, 2(4), 295-298. https://doi.org/10.1016/S0960-894X(01)80203-1

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 ). / Georg, Gunda I.; Cheruvallath, Zacharia S.; Himes, Richard H. et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 2, No. 4, 1992, p. 295-298.

Research output: Contribution to journal › Article › peer-review

Georg, GI, Cheruvallath, ZS, Himes, RH & Mejillano, MR 1992, '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 and Medicinal Chemistry Letters, vol. 2, no. 4, pp. 295-298. https://doi.org/10.1016/S0960-894X(01)80203-1

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abstract = "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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doi = "10.1016/S0960-894X(01)80203-1",

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AU - Georg, Gunda I.

AU - Cheruvallath, Zacharia S.

AU - Himes, Richard H.

AU - Mejillano, Magdalena R.

PY - 1992

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AB - 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.

KW - Taxol analogues

KW - cytotoxicity

KW - microtubule assembly

KW - synthesis

KW - β-lactams

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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 )

Abstract

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