Email this article 
Hide
Show all
OPEN ACCESS | 
PEER-REVIEWED |
RESEARCH ARTICLE
|
DOWNLOAD PDF
|
VIEW FULL-TEXT PDF
| TOTAL VIEWS
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.
Keywords
Full Text:
PDF
DOI: 10.5155/eurjchem.5.4.601-606.1096
Links for Article
| | | | | | |
| | | | | | |
| | |
Related Articles
Article Metrics
This Abstract was viewed 1396 times |
PDF Article downloaded 726 times
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
References
[1]. Rohloff, J. C.; Kent, K. M.; Postich, M. J.; Becker, M. W.; Chapman, H. H.; Kelly, D. E.; Lew, W.; Louie, M. S.; McGee, L. R.; Prisbe, E. J.; Schultze, L. M., Yu, R. H.; Zhang, L. J. Org. Chem. 1998, 63, 4545-4550.
http://dx.doi.org/10.1021/jo980330q
[2]. Federspiel, M.; Fischer, R.; Hennig, M.; Mair, H. J.; Oberhauser, T.; Rimmler, G.; Albiez, T.; Bruhin, J.; Estermann, H.; Gandert, C.; Göckel, V.; Götzö, S.; Hoffmann, U.; Huber, G.; Janatsch, G.; Lauper, S.; Röckel-Stäbler, O.; Trussardi, R.; Zwahlen, A. G. Org. Process Res. Dev. 1999, 3, 266-274.
http://dx.doi.org/10.1021/op9900176
[3]. Abrecht, S.; Harrington, P.; Iding, H.; Karpf, M.; Trussardi, R.; Wirz, B.; Zutter, U. Chimia 2004, 58, 621-629.
http://dx.doi.org/10.2533/000942904777677605
[4]. Karpf, M.; Trussardi, R. J. Org. Chem. 2001, 66, 2044-2051.
http://dx.doi.org/10.1021/jo005702l
[5]. Harrington, P. J.; Brown, J. D.; Foderaro, T.; Hughes, R. C. Org. Proc. Res. Dev. 2004, 8, 86-91.
http://dx.doi.org/10.1021/op0302107
[6]. Genovese, S.; Curini, M.; Epifano, F. Phytochemistry 2009, 70, 1082-1091.
http://dx.doi.org/10.1016/j.phytochem.2009.06.016
[7]. Floss, H. G. Nat. Prod. Rep. 1997, 14, 433-452.
http://dx.doi.org/10.1039/np9971400433
[8]. Kishore, G. M.; Shah, D. M. Annu. Rev. Biochem. 1988, 57, 627-663.
http://dx.doi.org/10.1146/annurev.bi.57.070188.003211
[9]. Zamir, L. O.; Luthe, C. Can. J. Chem. 1984, 62, 1169-1175.
http://dx.doi.org/10.1139/v84-191
[10]. Sutherland, J. K.; Watkins, W. J.; Snow, G. A.; Davies G. M. U. S. Patent 5 164 382, 1992.
[11]. Davies, G. M.; Barrett-Bee, K. J.; Jude, D. A.; Lehan, M.; Nichols, W. W.; Pinder, P. E.; Thain, J. L.; Watkins, W. J.; Wilson, R. G. Antimicrob. Agents Ch. 1994, 38, 403-406.
http://dx.doi.org/10.1128/AAC.38.2.403
[12]. Numata, A.; Iritani, M.; Yamada, T.; Minoura, K.; Matsumura, E.; Yamori, T.; Tsuruo T. Tetrahedron Lett. 1997, 38, 8215-8218.
http://dx.doi.org/10.1016/S0040-4039(97)10198-8
[13]. Aghil, O.; Bibby, M. C.; Carrington, S. J.; Double, J.; Douglas, K. T.; Phillips, R. M.; Shing, T. K. Anti-cancer Drug Des. 1992, 7, 67-82.
[14]. McConkey, G. A. Antimicrob. Agents Ch. 1999, 43, 175-177.
[15]. Johansson, L.; Liden, G. J. Biotechnol. 2006, 126, 528-545.
[16]. Yamada, T.; Iritani, M.; Ohishi, H.; Tanaka, K.; Minoura, K.; Doi, M.; Numata, A. Org. Biomol. Chem. 2007, 5, 3979-3986.
http://dx.doi.org/10.1039/b713060k
[17]. Nguyen, Q. C.; Doan, T. M. H.; Le, A. T.; Pham, X. V.; Tran, T. T. T.; Pham, V. C.; Nguyen, V. H. Tap. Chi. Hoa. Hoc. 2006, 44, 745-748.
[18]. Mosmann T. J. Immunol. Methods 1983, 65, 55-63.
[19]. Nie, L. D.; Shi, X. X. Tetrahedron-Asymmetry 2009, 20, 124-129.
http://dx.doi.org/10.1016/j.tetasy.2008.11.027
[20]. Liang-Deng, N.; Xiao-Xin, S.; Kwang, H. K.; Wei-Dong, L. J. Org. Chem. 2009, 74, 3970-3973.
http://dx.doi.org/10.1021/jo900218k
[21]. Yadav, J. S.; Reddy, B. V. S.; Kumar, G. M.; Murthy, C. V. S. R. Synthetic Commun. 2002, 32, 1797-1802.
http://dx.doi.org/10.1081/SCC-120004058
[22]. Lew, W.; Escarpe, P. A.; Mendel, D. B.; Sweeny, D. J.; Kim, C. U. Bioorg. Med. Chem. Lett. 1999, 9, 2811-2814.
http://dx.doi.org/10.1016/S0960-894X(99)00479-5
[23]. Oseltamivir Medical Review. US FDA Center for Drug Evaluation and Research, Application No. 021087, 25 October 1999.
[24]. Kim, C. U.; Lew, W.; Williams, M. A.; Liu, H.; Zhang, L.; Swaminathan, S.; Bischofberger, N.; Chen, M. S.; Mendel, D. B.; Tai, C. Y.; Laver, W. G.; Stevens, R. C. J. Am. Chem. Soc. 1997, 119, 681-690.
http://dx.doi.org/10.1021/ja963036t
How to cite
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.5.4.601-606.1096
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
Save to Zotero
Save to Mendeley
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
Refbacks
- There are currently no refbacks.
Copyright (c)
© Copyright 2010 - 2021 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2010-2021 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.