A computational study of open-chain epothilone analogue

Molecular mechanics (MM/Ambers) calculations were applied to probe the conformational profile of open‐chain epothilone analogue [Org Lett 2006, 8, 685], cytotoxic against some cell lines. Geometries of the most stable conformers were optimized at DFT level using the B3LYP functional and then compare...

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Bibliographic Details
Published in:International journal of quantum chemistry 2008, Vol.108 (5), p.967-973
Main Authors: Kamel, Karol, Rusinska-Roszak, Danuta
Format: Article
Language:English
Subjects:
anticancer agents
B3LYP
conformation
DFT
epothilone
hydrogen bonding
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Summary:Molecular mechanics (MM/Ambers) calculations were applied to probe the conformational profile of open‐chain epothilone analogue [Org Lett 2006, 8, 685], cytotoxic against some cell lines. Geometries of the most stable conformers were optimized at DFT level using the B3LYP functional and then compared to known both experimental and virtual conformers of epothilone. One of the most stable structures is III (1.47 kcal/mol above global minimum) which represents high similarity to the appropriate fragment of the Taylor's model of epothilone A, but two other conformers: XIV and XX, although they have almost the same conformation as the mother structure, are very unstable (6.7 and 12.4 kcal/mol above the global minimum). © 2007 Wiley Periodicals, Inc. Int J Quantum Chem, 2008
ISSN:0020-7608
1097-461X
DOI:10.1002/qua.21566