약학회지 (YAKHAK HOEJI)

  • 제50권6호
  • /
  • Pages.398-402
  • /
  • 2006
  • /
  • 0377-9556(pISSN)
  • /
  • 2383-9457(eISSN)
대한약학회 (The Pharmaceutical Society of Korea)
권호 표지

2-치환 플라본 유도체의 합성

Synthesis of 2-Substituted Flavone Derivatives

  • 단온화 (중앙대학교 약학대학 의약화학 교실) ;
  • 김수진 (중앙대학교 약학대학 의약화학 교실) ;
  • 임채욱 (중앙대학교 약학대학 의약화학 교실)
  • Dan, On-Wha (Division of Medicinal Chemistry, College of Pharmacy, Chung-ang University) ;
  • Kim, Su-Jin (Division of Medicinal Chemistry, College of Pharmacy, Chung-ang University) ;
  • Im, Chae-Uk (Division of Medicinal Chemistry, College of Pharmacy, Chung-ang University)
  • 발행 : 2006.12.31
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초록

Flavone was found to inhibit tyrosinase and reduce synthesis of melanin to show skin-lightening effect. With the hope of identifying skin-lightening flavones, we synthesized flavone analogs. Substituted benzoic acids (1) were treated with oxalyl chloride in DMF to yield benzoyl chlorides (2), which were reacted with 2-hydroxyacetophenones (3) to afford 2-benzoyloxyacetophenones (4). These acetophenones (4) were converted into 1,3-diketones (5) with base and then treated with acid to give flavone derivatives (6).

키워드

참고문헌

  1. 권경옥, 권영두, 김상진, 김주덕, 박성순, 이화순 : 신화장품학. 동화기술, 서울 p. 41, 201 (1997)
  2. Rao, Y. K., Fang, S. H. and Tzeng, Y. M. : Synthesis, growth inhibition, and cell cycle evaluations of novel flavonoid derivatives. Bioorganic & Medicinal Chemistry 13(24), 6850 (2005) https://doi.org/10.1016/j.bmc.2005.07.062
  3. Arima, H., Ashida, H. and Danno, G. I. : Rutin-enhanced antibacterial activities of flavonoids against Bacillus cereus and Salmonella enteritidis. Bioscience, Biotechnology, and Biochemistry 66(5), 1009 (2002) https://doi.org/10.1271/bbb.66.1009
  4. Amaral, A. C. F., Kuster, R. M., Goncalves, J. L. S. and Wigg, M. D. : Antiviral investigation on the flavonoids of Chamaesyce thymifolia. Fitoterapia 70(3), 293 (1999) https://doi.org/10.1016/S0367-326X(99)00008-8
  5. Park, K. H., Park, Y. D., Han, J. M., Im, K. R., Lee, B. W., Jeong, I. Y., Jeong, T. S. and Lee, W. S. : Anti-atherosclerotic and anti-inflammatory activities of catecholic xanthones and flavonoids isolated from Cudrania tricuspidata. Bioorganic & Medicinal Chemistry Letters 16(21), 5580 (2006) https://doi.org/10.1016/j.bmcl.2006.08.032
  6. Coskun, O., Kanter, M., Armutcu, F., Cetin, K., Kaybolmaz, B. and Yazgan, O. : Protective effects of quercetin, a flavonoid antioxidant, in absolute ethanol-induced acute gastric ulcer. European Journal of General Medicine 1(3), 37 (2004) https://doi.org/10.29333/ejgm/82201
  7. Masuda, T., Yamashita, Y. and Makara, T. : Skin-lightening cosmetics containing biflavonoids from Garcinia. JP 2005041821 A220050217 (2005)
  8. Yamaguchi, R. : Tyrosinase inhibitors, melanin formation inhibitors, fibroblast-proliferating agents, estrogenic agents, and skin-lightening and antiaging cosmetics. JP 2004083476 A2 20040318, (2004)
  9. Ha, T. J., Hwang, S. W., Jung, H. J., Park, K. H. and Yang, M. S. : Apigenin, tyrosinase inhibitor isolated from the flowers of Hemisteptia lyrata Bunge. Agricultural Chemistry and Biotechnology 45(4), 170, (2002)
  10. Sasaki, K. and Yoshizaki, F. : Nobiletin as a tyrosinase inhibitor from the peel of Citrus fruit. Biological & Pharmaceutical Bulletin 25(6), 806 (2002) https://doi.org/10.1248/bpb.25.806
  11. Sato, H. and Chofuku, H. : Tyrosinase inhibitors and cosmetics containing flavonoids. JP 10101543 A2 19980421 (1998)
  12. Wheeler, T. S. : Flavone. Organic Syntheses, Wiley, New York, Collect. 4, 478 (1963)