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Synthesis and biological evaluation of shikimic acid derivatives
Van Hung Nguyen (1)
, Van Cuong Pham (2,*) , Huong Doan Thi Mai (3) , Thanh Nguyen Le (4) , Thi Minh Hang Nguyen (5) , Van Nam Vu (6) , Huu Giap Tran (7) , Thi Thao Do (8) , Wim Dehaen (9) , Van Minh Chau (10) (1) Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet Road, Cau Giay, Hanoi, Vietnam
(2) Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet Road, Cau Giay, Hanoi, Vietnam
(3) Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet Road, Cau Giay, Hanoi, Vietnam
(4) Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet Road, Cau Giay, Hanoi, Vietnam
(5) Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet Road, Cau Giay, Hanoi, Vietnam
(6) Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet Road, Cau Giay, Hanoi, Vietnam
(7) Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet Road, Cau Giay, Hanoi, Vietnam
(8) Institute of Biotechnology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet Road, Cau Giay, Hanoi, Vietnam
(9) Department of Chemistry, Cathonic University of Leuven, Celestijnenlaan 200F 3001, Leuven, Belgium
(10) Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet Road, Cau Giay, Hanoi, Vietnam
(*) Corresponding Author
Received: 25 May 2014 | Revised: 14 Jul 2014 | Accepted: 17 Jul 2014 | Published: 31 Dec 2014 | Issue Date: December 2014
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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DOI: 10.5155/eurjchem.5.4.601-606.1096
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Funding information
Vietnam National Foundation for Science and Technology Development (NAFOSTED) and the Research Foundation Flanders (FWO) (Project No: 04/2010).
Citations
[1]. Nuno R. Candeias, Benedicta Assoah, Svilen P. Simeonov
Production and Synthetic Modifications of Shikimic Acid
Chemical Reviews 118(20), 10458, 2018
DOI: 10.1021/acs.chemrev.8b00350
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DOI Link: https://doi.org/10.5155/eurjchem.5.4.601-606.1096
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European Journal of Chemistry 2014, 5(4), 601-606 | doi: https://doi.org/10.5155/eurjchem.5.4.601-606.1096 | Get rights and content
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