European Journal of Chemistry 2014, 5(4), 601-606. doi:10.5155/eurjchem.5.4.601-606.1096

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, Accepted: 17 Jul 2014, Published: 31 Dec 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.


Keywords


Sulfur; Azides; Amines; Cytotoxicity; Asymmetric synthesis; Nucleophilic substitution

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DOI: 10.5155/eurjchem.5.4.601-606.1096

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[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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How to cite


Nguyen, V.; Pham, V.; Mai, H.; Le, T.; Nguyen, T.; Vu, V.; Tran, H.; Do, T.; Dehaen, W.; Chau, V. Eur. J. Chem. 2014, 5(4), 601-606. doi:10.5155/eurjchem.5.4.601-606.1096
Nguyen, V.; Pham, V.; Mai, H.; Le, T.; Nguyen, T.; Vu, V.; Tran, H.; Do, T.; Dehaen, W.; Chau, V. Synthesis and biological evaluation of shikimic acid derivatives. Eur. J. Chem. 2014, 5(4), 601-606. doi:10.5155/eurjchem.5.4.601-606.1096
Nguyen, V., Pham, V., Mai, H., Le, T., Nguyen, T., Vu, V., Tran, H., Do, T., Dehaen, W., & Chau, V. (2014). Synthesis and biological evaluation of shikimic acid derivatives. European Journal of Chemistry, 5(4), 601-606. doi:10.5155/eurjchem.5.4.601-606.1096
Nguyen, Van, 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. "Synthesis and biological evaluation of shikimic acid derivatives." European Journal of Chemistry [Online], 5.4 (2014): 601-606. Web. 19 Nov. 2019
Nguyen, Van, Pham, Van, Mai, Huong, Le, Thanh, Nguyen, Thi, Vu, Van, Tran, Huu, Do, Thi, Dehaen, Wim, AND Chau, Van. "Synthesis and biological evaluation of shikimic acid derivatives" European Journal of Chemistry [Online], Volume 5 Number 4 (31 December 2014)

DOI Link: https://doi.org/10.5155/eurjchem.5.4.601-606.1096

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