2-Arylethenylchromone Derivatives : Synthesis and Anticancer Activity

2-Arylethenylchronlones유도체의 합성 및 항암활성 검색

  • 문창상 (한국과학기술연구원 생체과학연구부 의약화학센터) ;
  • 이경원 (경희대학교 약학대학) ;
  • 이지용 (한국과학기술연구원 생체과학연구부 의약화학센터) ;
  • 이재열 (한국과학기술연구원 생체과학연구부 의약화학센터) ;
  • 정봉영 (고려대학교 화학과) ;
  • 이경태 (경희대학교 약학대학) ;
  • 이용섭 (한국과학기술연구원 생체과학연구부 의약화학센터)
  • Published : 2003.12.01

Abstract

2-Arylchromones, also known as flavones, are among the most ubiquitous classes of natural products occurring in the plant kingdom. On the other hand, 2-styrylchromones are relatively scarce in nature and only a few compounds has been isolated from the blue-green algae species. Therefore, new 2-arylethenylchromone derivatives ( 4a∼n, 5a∼f) were synthesized by the aldol condensation of 2-methylchromone ( 3) with several aromatic aldehydes in order to evaluate their cytotoxicities using a MTT assay on three tumor cells. 2-Arylethenylchromone derivative 4a showed the significant cytotoxic activities on KB, HL-60 and P-388 cell lines with $IC_{50}$/ values of 25.2, 63.59 and 49.51 $\mu$M, respectively, indicating that 2-arylethenylchromone skeleton has a potential anti-tumor application.

Keywords

References

  1. Gerwik, W. H., Lopez, A., Van Duyne, G. D., Clardy, J., Ortiz, W. and Baez, A. : Hormothamnione, a novel cytotoxic styrylchromone from the marine cyanophyte hormothamnion enteromorphoides grunow. Tetrahedron Lett. 27, 1979 (1986) https://doi.org/10.1016/S0040-4039(00)84426-3
  2. Gerwik, W. H. : 6-Desmethoxyhormothamnione, A new cytotoxic strylchromone from the marine cryptophyte chrysophaeum taylori. J. Nat. Prod. 52, 252 (1989) https://doi.org/10.1021/np50062a005
  3. Pinto, D. C. G. A., Silva, A. M. S. and Cavaleire, J. A. S. : A convenient synthesis of (E)-5-hydroxy-2-styrylchromones by modification of the Baker-Venkataraman method. New J. Chem. 24, 85 (2000) https://doi.org/10.1039/a908539d
  4. Yokoe, I., Higuchi, K, Shrataki, Y. and Komatsu, M. : Photochemistry of flavonoids. V. Photocyclization of 2-styryl-4H-chromene-4-ones. Chem. Pharm. Bull. 29, 2670 (1981)
  5. Pinto, D. C. G. A., Silva, A. M. S., Cavaleire, J. A. S., Foces-Foces, C., Liamas-Saiz, A. L., jagerovic, N. and Elguero, J. : Synthesis and molecular structure of 3-(2-benzyloxy-6-hydroxyphenyl)-5-styrylpyrazoles. Reaction of 2-styrylchro-mones and hydrazine hydrate. Tetrahedron 55, 10187 (1999)
  6. Reddy, B. P. and Krupadanam, G. L. D. : The synthesis of 8-allyl- 2-styrylchromones by the modified Baker-Venkataraman transformation. J. Het. Chem. 33, 1561 (1996) https://doi.org/10.1002/jhet.5570330602
  7. Rao, C. B., Subramanyam, G. and Venkateswrlu, V. : Synthesis of chromone. II. Some derivatives of 7-hydroxy-2-methylchro-mone. J. Org. Chem. 52, 683 (1959)
  8. Chatterjee, A. and Biswas, K. M. : Acylation of indoles by duff reaction and Vilsmeier-Haack formylation and conformation of N-formylindoles. J. Org. Chem. 38, 4002 (1973) https://doi.org/10.1021/jo00987a009
  9. Hollinshed, S. P. : Stereoselective Synthesis of Highly func-tionalised pyrrolidines via 1,3-dipolar cycioaddition reactions on a solid support. Tetrahedron Lett. 51, 9157 (1996)