Please use this identifier to cite or link to this item: https://doi.org/10.1021/jm9905662
Title: Synthesis and evaluation of tryprostatin B and demethoxyfumitremorgin C analogues
Authors: Wang, H. 
Usui, T.
Osada, H.
Ganesan, A. 
Issue Date: 20-Aug-2000
Citation: Wang, H., Usui, T., Osada, H., Ganesan, A. (2000-08-20). Synthesis and evaluation of tryprostatin B and demethoxyfumitremorgin C analogues. Journal of Medicinal Chemistry 43 (8) : 1577-1585. ScholarBank@NUS Repository. https://doi.org/10.1021/jm9905662
Abstract: Tryprostatin B and demethoxyfumitremorgin C are fungal inhibitors of mammalian cell cycle progression at the G2/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-β-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-β-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.
Source Title: Journal of Medicinal Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/112098
ISSN: 00222623
DOI: 10.1021/jm9905662
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