Synthesis and evaluation of tryprostatin B and demethoxyfumitremorgin C analogues


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).

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Description/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.

Item Type: Article
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Keywords: mammalian-cell cycle, pictet-spengler reaction, dna topoisomerase-ii, aspergillus-fumigatus, spirotryprostatin-b, g2/m phase, inhibitors, fumitremorgins, azatoxin, cleavage
Subjects: Q Science
Q Science > QD Chemistry
Divisions: University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 18885
Date Deposited: 05 Jan 2006
Last Modified: 27 Mar 2014 18:08
URI: http://eprints.soton.ac.uk/id/eprint/18885

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