약학회지 (YAKHAK HOEJI)

  • 제53권2호
  • /
  • Pages.89-92
  • /
  • 2009
  • /
  • 0377-9556(pISSN)
  • /
  • 2383-9457(eISSN)
대한약학회 (The Pharmaceutical Society of Korea)
권호 표지

Bis(pyronyl)acrylic Acid Ester 유도체의 합성

Synthesis of Bis(pyronyl)acrylic Acid Ester Derivatives

  • 남승옥 (경희대학교 약학대학 나노의약생명과학과 의약화학실) ;
  • 김동한 (경희대학교 약학대학 나노의약생명과학과 의약화학실) ;
  • 이용섭 (경희대학교 약학대학 나노의약생명과학과 의약화학실)
  • Nam, Seung-Ok (Medicinal Chemistry Laboratory, Department of Life and Nanopharmaceutical Science, Kyung Hee University) ;
  • Kim, Dong-Han (Medicinal Chemistry Laboratory, Department of Life and Nanopharmaceutical Science, Kyung Hee University) ;
  • Lee, Yong-Sup (Medicinal Chemistry Laboratory, Department of Life and Nanopharmaceutical Science, Kyung Hee University)
  • 발행 : 2009.04.30
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

Dicaffeoyltartaric acid has a structural feature consisting of two caffeic acid units separated by tartaric acid linker and has been found to be a potent inhibitor of HIV-1 integrase and an antioxidant. In this study, bis(pyronyl)acrylic acid esters joined through a 5-membered ring as a linker were synthesized as the analogues of dicaffeoyltartaric acid.

키워드

참고문헌

  1. Cheng, J.-C., Dai, F., Zhou, B., Yang, L. and Liu, Z.-L. : Antioxidant activity of hydroxycinnamic acid derivatives in human low density lipoprotein: Mechanism and structureactivity relationship. Food Chemistry 104, 132 (2007) https://doi.org/10.1016/j.foodchem.2006.11.012
  2. Fiuza, S. M., Gomes, C., Teixeira, L. J., Girao da Cruz, M. T., Cordeiro, M. N. D. S., Milhazes, N., Borges, F. and Marques, M. P. M. : Phenolic acid derivatives with potential anticancer properties-a structure-activity relationship study. Part 1: methyl, propyl and octyl esters of caffeic and gallic acids. Bioorg. Med. Chem. 12, 3581 (2004) https://doi.org/10.1016/j.bmc.2004.04.026
  3. Uwai, K., Osanai, Y., Imaizumi, T., Kanno, S.-i., Takeshita, M. and Ishikawa, M. : Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages. Bioorg. Med. Scheme 1 Chem. 16, 7795 (2008) https://doi.org/10.1016/j.bmc.2008.07.006
  4. Scarpati, M. L. and Oriente, G. : Chicoric acid (dicaffeyltartaric acid): Its Isolation from chicory (Chicorium intybus) and synthesis. Tetrahedron 4, 43 (1958) https://doi.org/10.1016/0040-4020(58)88005-9
  5. Thygesen, L., Thulin, J., Mortensen, A., Skibsted, L. H. and Molgaard, P. : Antioxidant activity of cichoric acid and alkamides from Echinacea purpurea, alone and in combination. Food Chemistry 101, 74 (2006)
  6. Charvat, T. T., Lee, D. J., Robinson, W. E. and Chamberlin, A. R. : Design, synthesis, and biological evaluation of chicoric acid analogs as inhibitors of HIV-1 integrase. Bioorg. Med. Chem. 14, 4552 (2006) https://doi.org/10.1016/j.bmc.2006.02.030
  7. King, P. J., Ma, G., Miao, W., Jia, Q., McDougall, B. R., Reinecke, M. G., Cornell, C., Kuan, J., Kim, T. R. and Robinson, W. E. Jr. : Structure-Activity Relationships: Analogs of the Dicaffeoylquinic and Dicaffeoyltartaric Acids as Potent Inhibitors of Human Immunodeficiency Virus Type 1 Integrase and Replication. J. Med. Chem. 42, 497 (1999) https://doi.org/10.1021/jm9804735
  8. Hwang, D. J., Kim, S. N., Choi, J. H. and Lee, Y. S. : Dicaffeoylor digalloyl pyrrolidine and furan derivatives as HIV integrase inhibitors. Bioorg. Med. Chem. 9, 1429 (2001) https://doi.org/10.1016/S0968-0896(01)00013-X
  9. Kim, S. N., Lee, J. Y., Kim, H. J., Shin, C. G., Park, H. and Lee, Y. S. : Synthesis and HIV-1 integrase inhibitory activities of caffeoylglucosides. Bioorg. Med. Chem. Lett. 10, 1879-82 (2000) https://doi.org/10.1016/S0960-894X(00)00355-3
  10. Bringmann, G., Gunther, C. and Jumbam, D. N. : Isolation of 4-O-$\beta$-D-glucopyranosylcaffeic acid and gallic acid from Cyathea dregei KUNZE (Cyatheaceae). Pharmaceutical and Pharmacological Letters 9, 41 (1999)
  11. Kang, S. S., Kim, H. J., Jin, C. and Lee, Y. S. : Synthesis of tyrosinase inhibitory (4-oxo-4H-pyran-2-yl)acrylic acid ester derivatives. Bioorg. Med. Chem. Lett. 19, 188 (2009) https://doi.org/10.1016/j.bmcl.2008.10.119
  12. Ohta, S., Shimabayashi, A., Aono, M. and Okamoto, M. : A general convenient one-pot procedure for the conversion of carboxylic acids into their tert-butyl esters which is also applicable to aliphatic carboxylic acids. Synthesis 833 (1982)