European Journal of Chemistry

Synthesis and biological evaluation of shikimic acid derivatives



Main Article Content

Van Hung Nguyen
Van Cuong Pham
Huong Doan Thi Mai
Thanh Nguyen Le
Thi Minh Hang Nguyen
Van Nam Vu
Huu Giap Tran
Thi Thao Do
Wim Dehaen
Van Minh Chau

Abstract

From shikimic acid, new series of oseltamivir analogues containing either ether sulfur or ether oxygen at C-3 position were prepared and evaluated for their biological activities. This is the first report on synthesis of oseltamivir analogues with ether sulfur at C-3. Except for compounds 4d, 4f, 7c and 7d, the remaining compounds were found to be active against MCF-7, LU-1 and KB cell lines. As oseltamivir had no cytotoxicity against different cell lines such as MCF-7, LU-1, KB, MDCK, MRC-5, VERO, MK and 293, the modification of alkyl groups at C-3 of the oseltamivir ring framework could significantly increase the cytotoxicity for this class of compounds. Loss of neuraminidase inhibition activity of these synthetic oseltamivir analogues suggested that the alkyl ether groups at C-3 should be critical for their anti-neuraminidase activity.


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Nguyen, V. H.; Pham, V. C.; Mai, H. D. T.; Le, T. N.; Nguyen, T. M. H.; Vu, V. N.; Tran, H. G.; Do, T. T.; Dehaen, W.; Chau, V. M. Synthesis and Biological Evaluation of Shikimic Acid Derivatives. Eur. J. Chem. 2014, 5, 601-606.

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Supporting Agencies

Vietnam National Foundation for Science and Technology Development (NAFOSTED) and the Research Foundation Flanders (FWO) (Project No, 04/2010).
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