Planta Med 2006; 72 - P_091
DOI: 10.1055/s-2006-949891

Synthesis and biological activity of a new benzothiazol derivative of curcumin

MC Lozada 1, EV Avila 2, JL Montiel 3, ML Villarreal 3, RG Enríquez 4, D Gnecco 5
  • 1Departamento de Sistemas Biológicos, UAM-Xochimilco, Calzada del Hueso 1100, Villa Quietud, Coyoacán, 04960, D. F, México
  • 2Departamento de Ciencias de la Salud, UAM-Iztapalapa, Av. San Rafael Atlixco 186, Vicentina, Iztapalapa, 09340, D. F, México
  • 3Universidad Autónoma del Estado de Morelos Av. Universidad 1001, 62210, Morelos, México
  • 4Instituto de Química, UNAM, Cd. Universitaria, Coyoacán, 04510, D. F, México
  • 5Centro de Química, Instituto de Ciencias, BUAP, 72000, Puebla, México

Recently much attention has been focused in the research of curcumin, a secondary metabolite isolated from Curcuma longa L. and from other species of Curcuma. Current investigation of curcumin is fastly increasing due to its biological activities (anti-inflammatory, [1] antioxidant, anti-HIV, [2] including cytotoxic effects on several cancer line cells [3, 4] and upon cystic fibrosis [5]).

A benzothiazol derivative of curcumin was obtained by systematic structural modification of curcumin (Scheme). We have described previously the synthesis of new heterocyclic derivatives of curcumin including the compound 4 [6].

The benzothiazol 4 was prepared by the reaction of 3 and 2-aminobenzenethiol. During the ring formation a part of the molecule of curcumin suffered fragmentation. The structure of 4 was assessed by spectroscopic methods (IR, 1D and 2D NMR, mass spectrometry), also the crystal structure was analyzed by X-ray crystallography.

In our preliminary biological studies, compound 4 has shown important cytotoxic effect toward a nasopharyngeal carcinoma cell line KB (ED50 =3.38µg/mL) as well as modification of the percentage of cells on cell cycle phases of the monocytic human cell line TPH1.

Acknowledgements: CONACYT of México (37821-N and 40959-Q); DGAPA of UNAM (IN232202).

References: 1. Ali, M., et al. (1995), Ind. J. Chem. 34B: 884. 2. Artico, M., et al. (1998), J. Med. Chem., 41: 3948. 3. Huang, M.T., et al. (1992), ACS Symposium Series 507: 338. 4. Ishida, J. et al. (2002), Biorg. Med. Chem. 10: 3481. 5. Egan, M. F. et al. (2004), Science, 304: 600. 6. M. Concepción Lozada, et al., (2004), Heterocycles 65: 49.