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Synthesis and evaluation of tryprostatin B and demethoxyfumitremorgin C analogues

Synthesis and evaluation of tryprostatin B and demethoxyfumitremorgin C analogues
Synthesis and evaluation of tryprostatin B and demethoxyfumitremorgin C analogues
Tryprostatin B and demethoxyfumitremorgin C are fungal inhibitors of mammalian cell cycle progression at the G(2)/M transition. N-Alkyl derivatives of the L-TrP-L-Pro diketopiperazine were prepared as analogues of tryprostatin B, and two of these were more active than the natural product. A second series of cis- and trans-tetrahydro-beta-carbolines annulated to a diketopiperazine were prepared as analogues of demethoxyfumitremorgin C. The nature of the alkyl substituent, as well as its cis or trans relationship in the tetrahydro-beta-carboline ring, was found to have a significant effect on cytotoxic activity. Small cis-alkyl substituents fall into the demethoxyfumitremorgin C family, whereas bulky benzyl trans compounds appear to act via a different mechanism of action.
mammalian-cell cycle, pictet-spengler reaction, dna topoisomerase-ii, aspergillus-fumigatus, spirotryprostatin-b, g2/m phase, inhibitors, fumitremorgins, azatoxin, cleavage
0022-2623
1577-1585
Wang, H. S.
95a22b69-5405-4653-91d3-9bf3888c0b94
Usui, T.
06430abb-aa70-4af8-b14c-c0c0badd6571
Osada, H.
7424e294-ca6d-4297-b682-e19cf426d99f
Ganesan, A.
62aa5a87-9308-4383-8686-99726b6bcfb9
Wang, H. S.
95a22b69-5405-4653-91d3-9bf3888c0b94
Usui, T.
06430abb-aa70-4af8-b14c-c0c0badd6571
Osada, H.
7424e294-ca6d-4297-b682-e19cf426d99f
Ganesan, A.
62aa5a87-9308-4383-8686-99726b6bcfb9

Wang, H. S., Usui, T., Osada, H. and Ganesan, A. (2000) Synthesis and evaluation of tryprostatin B and demethoxyfumitremorgin C analogues. Journal of Medicinal Chemistry, 43 (8), 1577-1585. (doi:10.1021/jm9905662).

Record type: Article

Abstract

Tryprostatin B and demethoxyfumitremorgin C are fungal inhibitors of mammalian cell cycle progression at the G(2)/M transition. N-Alkyl derivatives of the L-TrP-L-Pro diketopiperazine were prepared as analogues of tryprostatin B, and two of these were more active than the natural product. A second series of cis- and trans-tetrahydro-beta-carbolines annulated to a diketopiperazine were prepared as analogues of demethoxyfumitremorgin C. The nature of the alkyl substituent, as well as its cis or trans relationship in the tetrahydro-beta-carboline ring, was found to have a significant effect on cytotoxic activity. Small cis-alkyl substituents fall into the demethoxyfumitremorgin C family, whereas bulky benzyl trans compounds appear to act via a different mechanism of action.

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More information

Published date: 20 April 2000
Keywords: mammalian-cell cycle, pictet-spengler reaction, dna topoisomerase-ii, aspergillus-fumigatus, spirotryprostatin-b, g2/m phase, inhibitors, fumitremorgins, azatoxin, cleavage

Identifiers

Local EPrints ID: 18885
URI: http://eprints.soton.ac.uk/id/eprint/18885
ISSN: 0022-2623
PURE UUID: d70e9467-d727-4aff-a4bc-2d821a2732e3

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Date deposited: 05 Jan 2006
Last modified: 15 Mar 2024 06:08

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Contributors

Author: H. S. Wang
Author: T. Usui
Author: H. Osada
Author: A. Ganesan

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