Chemical Synthesis and Biological Evaluation of C-2 Taxoids

K. C. Nicolaou; J. Renaud; P. G. Nantermet; E. A. Couladouros; R. K. Guy; W. Wrasidlo

doi:10.1021/ja00114a005

Chemical Synthesis and Biological Evaluation of C-2 Taxoids

K. C. Nicolaou, J. Renaud, P. G. Nantermet, E. A. Couladouros, R. K. Guy, W. Wrasidlo

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Abstract

An efficient, general method for the synthesis of 1,2-hydroxy esters by regioselective nucleophilic opening of 1,2-cyclic carbonate systems has been developed. A reliable and practical route giving access to the taxoid carbonate 2 from the readily available 10-deacetylbaccatin III (13) has been established. Nucleophilic opening of the carbonate 2 with a variety of nucleophiles provided a number of novel C-2 Taxols. Water-soluble taxoid onium salts (e.g., 31e, 31n, 32, and 34b) were also synthesized and studied. A selected number of taxoids were subjected to cytotoxicity and tubulin polymerization assays as well as in vivo studies. The results of these studies are reported herein.

Original language	English
Pages (from-to)	2409-2420
Number of pages	12
Journal	Journal of the American Chemical Society
Volume	117
Issue number	9
DOIs	https://doi.org/10.1021/ja00114a005
State	Published - 1995

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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title = "Chemical Synthesis and Biological Evaluation of C-2 Taxoids",

abstract = "An efficient, general method for the synthesis of 1,2-hydroxy esters by regioselective nucleophilic opening of 1,2-cyclic carbonate systems has been developed. A reliable and practical route giving access to the taxoid carbonate 2 from the readily available 10-deacetylbaccatin III (13) has been established. Nucleophilic opening of the carbonate 2 with a variety of nucleophiles provided a number of novel C-2 Taxols. Water-soluble taxoid onium salts (e.g., 31e, 31n, 32, and 34b) were also synthesized and studied. A selected number of taxoids were subjected to cytotoxicity and tubulin polymerization assays as well as in vivo studies. The results of these studies are reported herein.",

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year = "1995",

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T1 - Chemical Synthesis and Biological Evaluation of C-2 Taxoids

AU - Nicolaou, K. C.

AU - Renaud, J.

AU - Nantermet, P. G.

AU - Couladouros, E. A.

AU - Guy, R. K.

AU - Wrasidlo, W.

PY - 1995

Y1 - 1995

N2 - An efficient, general method for the synthesis of 1,2-hydroxy esters by regioselective nucleophilic opening of 1,2-cyclic carbonate systems has been developed. A reliable and practical route giving access to the taxoid carbonate 2 from the readily available 10-deacetylbaccatin III (13) has been established. Nucleophilic opening of the carbonate 2 with a variety of nucleophiles provided a number of novel C-2 Taxols. Water-soluble taxoid onium salts (e.g., 31e, 31n, 32, and 34b) were also synthesized and studied. A selected number of taxoids were subjected to cytotoxicity and tubulin polymerization assays as well as in vivo studies. The results of these studies are reported herein.

AB - An efficient, general method for the synthesis of 1,2-hydroxy esters by regioselective nucleophilic opening of 1,2-cyclic carbonate systems has been developed. A reliable and practical route giving access to the taxoid carbonate 2 from the readily available 10-deacetylbaccatin III (13) has been established. Nucleophilic opening of the carbonate 2 with a variety of nucleophiles provided a number of novel C-2 Taxols. Water-soluble taxoid onium salts (e.g., 31e, 31n, 32, and 34b) were also synthesized and studied. A selected number of taxoids were subjected to cytotoxicity and tubulin polymerization assays as well as in vivo studies. The results of these studies are reported herein.

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M3 - Article

AN - SCOPUS:0000585732

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EP - 2420

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 9

ER -

Chemical Synthesis and Biological Evaluation of C-2 Taxoids

Abstract

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