European Journal of Chemistry

Synthesis of new curcumin analogues from Claisen-Schmidt condensation



Main Article Content

Nouara Ziani
Assia Sid
Albert Demonceau
Quentin Willem
Benjamin Dassonneville
Kaddour Lamara

Abstract

A series of new curcumin analogues were obtained by Claisen-Schmidt condensation of substituted benzaldehydes with cyclohexanone derivatives using the ratio of 1:2 of ketone to aldehyde in dilute ethanolic solution under base catalyzed (NaOH) conditions at room temperature in good yields. The structures of the synthesized compounds were confirmed by data of IR, 1H NMR, and 13C NMR spectra.

4_2_146_148

icon graph This Abstract was viewed 2553 times | icon graph Article PDF downloaded 1070 times

How to Cite
(1)
Ziani, N.; Sid, A.; Demonceau, A.; Willem, Q.; Dassonneville, B.; Lamara, K. Synthesis of New Curcumin Analogues from Claisen-Schmidt Condensation. Eur. J. Chem. 2013, 4, 146-148.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Kuttan, R.; Sudheeran, P. C.; Josph, C. D. Cancer Lett. 1985, 29, 197-202.
http://dx.doi.org/10.1016/0304-3835(85)90159-4

[2]. Kuttan, R.; Sudheeran, P. C.; Josph, C. D. Tumori. 1987, 73, 29-31.
PMid:2435036

[3]. Cole, G. M. T.; Morihara, G. P.; Yang, F. A.; Begum, S. A.; Frautschy, A. N. Y. Acad. Sci. 2004, 1035, 68-84.
http://dx.doi.org/10.1196/annals.1332.005
PMid:15681801

[4]. Cheng, A. L.; Hsu, C. H.; Lin. J. K.; Hsu, M. M.; Ho, Y. F.; Shen, T. S.; Ko, J. Y.; Lin, J. T.; Lin, B. R.; Ming-Shiang, W.; Yu, H. S.; Jee, S. H.; Chen, G. S.; Chen, T. M.; Chen, C. A.; Lai, M. K.; Pu, Y. S.; Pan, M. H.; Wang, Y. J.; Tsai, C. C.; Hsieh, C. Y. Anticancer Res. 2001, 21, 2895-2900.
PMid:11712783

[5]. Gescher, A. J. Chemother. 2004, 4, 3-6.

[6]. Vajragupta, O.; Boonchoong, P.; Morris, G. M.; Olson, A. J. Bioorg. Med. Chem. Lett. 2005, 15, 3364-3368.
http://dx.doi.org/10.1016/j.bmcl.2005.05.032
PMid:15950462

[7]. Reddy, R. C.; Vatsaala, P. G.; Keshamouni, V. G.; Padmanaban, G.; Rangarajan, P. N. Biochem. Biophy. Res. Commun. 2005, 326, 472-474.
http://dx.doi.org/10.1016/j.bbrc.2004.11.051
PMid:15582601

[8]. Hsu, C. H.; Cheng, A. L. Adv. Exp. Med. Biol. 2007, 595, 471-480.
http://dx.doi.org/10.1007/978-0-387-46401-5_21
PMid:17569225

[9]. Pan, M. H.; Huang, T. M.; Lin, J. K. Drung Metab. Dispos. 2000, 27, 486-494.

[10]. Sharma, R. A.; Steward, W. P.; Gescher, A. J. Adv. Exp. Med. Biol. 2007, 595, 453-470.
http://dx.doi.org/10.1007/978-0-387-46401-5_20
PMid:17569224

[11]. Dimmock, J. R.; Arora, V. K.; Wonko, S. L.; Hamon, N. W.; Quail, J. W.; Jia, Z.; Warrington, R. C.; Fang, W. D.; Lee, J. S. Drug Des. Deliv. 1990, 6, 183-194.
PMid:2076179

[12]. Dimmock, J. R.; Nyathi, C. B.; Smith, P. J. J. Pharm. Sci. 1978, 67, 1543-1546.
http://dx.doi.org/10.1002/jps.2600671113

[13]. Broom, A. D.; Shim, J. L.; Anderson, G. L. J. Org. Chem. 1976, 41, 1095-1099.
http://dx.doi.org/10.1021/jo00869a003

[14]. Grivsky, E. M.; Lee, S.; Sigel, C. W.; Duch, D. S.; Nichol, C. A. J. Med. Chem. 1980, 23, 327-329.
http://dx.doi.org/10.1021/jm00177a025

[15]. Matsumoto, J.; Minami, S. J. Med. Chem. 1975, 18, 74-79.
http://dx.doi.org/10.1021/jm00235a017

[16]. Suzuki, N. Chem. Pharm. Bull. 1980, 28, 761-763.
http://dx.doi.org/10.1248/cpb.28.761

[17]. Deyanov, A. B.; Niyazov, R. K.; Nazmetdinov, F. Y.; Syropytov, B. Y.; Kolla, V. E.; Konshin, M. E. Khim. Farm. Zh. 1991, 25, 26-28.

[18]. Agarwal, A.; Ashutosh, R.; Goyal, N.; Chauhan, P. M. S.; Gupta, S. Bioorg. Med. Chem. 2005, 13, 6226-6232.
http://dx.doi.org/10.1016/j.bmc.2005.06.052
PMid:16054819

[19]. Behr, L. C.; Fusco, F.; Jarboe, C. H. In Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings; Wiley, R.H., Ed. The Chemistry of Heterocyclic compounds; Wiley- Interscience: New York, NY. 1967.

[20]. Sid, A.; Lamara, K.; Moktari, M.; Ziani, N.; Mosset, P. Eur. J. Chem. 2011, 2(3), 311-313.
http://dx.doi.org/10.5155/eurjchem.2.3.311-313.414

[21]. Ziani, N.; Lamara, K.; Sid, A.; Willem, Q.; Dassonneville, B.; Demonceau, A. Eur. J. Chem. 2013, 4(2), 176-179.

http://dx.doi.org/10.5155/eurjchem.4.2.176-179.757

[22]. Kok, W. L.; Chau, L. T.; Choi, Y. L.; Ahmad, S. M; Basyaruddin, A, R.; Daud, A. I.; Nordin, H. L. Med. Chem. Res. 2012, 21, 333-344.

Supporting Agencies

Laboratory of Applied Chemistry and Materials Technology, Chemistry Institute, University Larbi Ben M’hidi of Oum El Bouaghi, Rue de Constantine, 04000, Algeria
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).