Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Synthesis, Cytotoxicity and Antitumor Activity of 2,3-Diarylcyclopent-2-ene-1-ones

  • Nam, Nguyen-Hai (College of Pharmacy, Chungnam National University) ;
  • Kim, Yong (College of Pharmacy, Chungnam National University) ;
  • You, Young-Jae (College of Pharmacy, Chungnam National University) ;
  • Hong, Dong-Ho (College of Pharmacy, Chungnam National University, Research Institute of Biosciences and Biotechnology) ;
  • Kim, Hwan-Mook (Research Institute of Biosciences and Biotechnology) ;
  • Ahn, Byung-Zun (College of Pharmacy, Chungnam National University)
  • Published : 2002.10.01
Download PDF
⟨ Previous Next ⟩

Abstract

Two series of 2,3-diarylcyclopent-2-ene-1-ones including 2-aryl-3-(2,5-dihydroxyphenyl)cyclopent-2-ene-1-ones (2a∼2f) and 3-aryl-2-(3',4',5'-trimethoxyphenyl)cyclopent-2-ene-1-one (3a∼3j) were synthesized and evaluated for the cytotoxicity against three tumor cell lines; B16F10, HCT116 and A431. It was found that the 3,4,5-trimethoxy substituent was optimal for the bioactivity of compounds in series 2. Meanwhile, compounds in series 3 exhibited the most potent cytotoxicity with 3-aryl ring being 4-methoxyphenyl (compound 3f), (3-hydroxy-4-methoxy)phenyl (compound 3e), or (3-amino-4-methoxy)phenyl (compound 3j).

Keywords

References

  1. Kim, Y., Kim, S. B., You, Y. J., Ahn, B. Z. Deoxypodophyllotoxin; The Cytotoxic and Antiangiogenic Component from Pulsatilla koreana. Planta Med., 68, 271 (2002) https://doi.org/10.1055/s-2002-23140
  2. Nam, N. H., You, Y. J., Kim, Y., Hong D. H., Kim, H. M., Ahn, B. Z., Combretoxazolones: Syntheses and biological activity. Bioorg. Med. Chem. Lett., 11, 3073-3076 (2001a) https://doi.org/10.1016/S0960-894X(01)00622-9
  3. Nam, N. H., You, Y. J., Kim, Y., Hong D. H., Kim, H. M., Ahn, B. Z., Syntheses of Certain 3-Aryl-2-propenoates and Evaluation of their Cytotoxicity. Bioorg. Med. Chem. Lett., 11, 1173-1176 (2001b). https://doi.org/10.1016/S0960-894X(01)00165-2
  4. Nam, N. H., You, Y. J., Kim, Y., Hong D. H., Kim, H. M., Ahn, B. Z., Synthesis and Cytotoxicity of Some Rigid Derivatives of Methyl 2,5-Dihydroxycinnamates. Submitted to Arch. Pharm. Res. (2002a)
  5. Nam, N. H., You, Y. J., Kim, Y., Hong D. H., Kim, H. M., Ahn, B. Z., Antitumor, Antiangiogenic and Antiinvasive Activity of the Ephedra Sinica Extract. Phytother. Res., In press (2002b)
  6. Nam, N. H., You, Y. J., Kim, Y., Hong D. H., Kim, H. M., Ahn, B. Z., Synthesis and Antitumor Activity of Novel Combretastatins: Combretocyclopentenones and Related Analogues. Bioorg. Med. Chem. Lett., 12, 1955-1958 (2002c) https://doi.org/10.1016/S0960-894X(02)00321-9
  7. Nam, N. H., You, Y. J., Kim, Y., Hong D. H., Kim, H. M., Ahn, B. Z., Synthesis and Antitumor Activity of Water Soluble Prodrugs of 3-[(3-Amino-4-methoxy)phenyl]-2-(3,4,5-trime-thoxyphenyl)cyclopent-2-ene-1-one. Bioorg. Med. Chem., Submitted (2002d)
  8. Skehan, P., Storeng, R., Scudiero, D., Monk,A., MacMahon,J., Vistica, D., Warren, J., Bokesch, H., Kenny, S., Boyd, M. R. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Nat. Cancer Inst., 82, 1107 (1990) https://doi.org/10.1093/jnci/82.13.1107