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.

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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.

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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.

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