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






  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


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

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.5.4.601-606.1096

Links for Article


| | | | | | |

| | | | | | |

Related Articles




Article Metrics

This Abstract was viewed 1086 times | PDF Article downloaded 622 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


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. 15 Aug. 2020
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)

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 - 2020  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 2010-2020 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.

hatay escort hatay escort corlu escort corum escort burgaz escort giresun escort aydin escort ordu escort erzincan escort hatay escort sivas escort rize escort edirne escort aksaray escort kibris escort isparta escort erzurum escort tekirdag escort usak escort urfa escort kastamonu escort kibris escort manisa escort giresun escort urfa escort nevsehir escort sivas escort yalova escort ordu escort hatay escort yalova escort amasya escort kayseri escort ordu escort maras escort canakkale escort yalova escort balikesir escort manisa escort urfa escort mugla escort trabzon escort bolu escort corlu escort diyarbakir escort isparta escort kutahya escort elazig escort erzurum escort sakarya escort afyon escort kutahya escort konya escort agri escort cesme escort sinop escort sivas escort konya escort kibris escort adapazari escort luleburgaz escort adana escort kibris escort rize escort sakarya escort alanya escort isparta escort burdur escort konya escort bitlis escort canakkale escort sivas escort amasya escort mus escort aydin escort van escort yalova escort kastamonu escort mardin escort bolu escort afyon escort sakarya escort isparta escort tokat escort trakya escort bayburt escort urfa escort mardin escort