Bulletin of the Korean Chemical Society

  • 제33권8호
  • /
  • Pages.2585-2591
  • /
  • 2012
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Heterocyclic Chalcone Derivatives and Their Radical Scavenging Ability Toward 2,2-Diphenyl-1-Picrylhydrazyl (DPPH) Free Radicals

  • Hwang, Ki-Jun (Research Center of Bioactive Materials, College of Natural Science, Chonbuk National University) ;
  • Kim, Ho-Seok (Research Center of Bioactive Materials, College of Natural Science, Chonbuk National University) ;
  • Han, In-Cheol (Department of Bioactive Material Sciences, College of Natural Science, Chonbuk National University) ;
  • Kim, Beom-Tae (Research Center of Bioactive Materials, College of Natural Science, Chonbuk National University)
  • 투고 : 2012.04.24
  • 심사 : 2012.05.07
  • 발행 : 2012.08.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

A series of heterocyclic chalcone derivatives bearing heterocycles such as thiophene or furan ring as an isostere of benzene ring were carefully prepared, and the influence of heterocycles on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities was systematically investigated. Structure-activity relationships (SAR) analysis showed that the activities of thiophene ring-containing chalcones were higher than those of furan ring-containing chalcones, and the presence of methyl substituent of heterocyclic ring distinctly affected the activities compared with non-substituted heterocycles in an opposite manner, with the 4'-methyl group of thiophene ring increasing activity and the 3'-methyl group of the furan ring decreasing activity. The distinct isosteric effect of heterocycles (i.e., thiophene or furan ring) on radical scavenging activities of heterocyclic chalones was distinctly demonstrated in our work.

키워드

참고문헌

  1. Dimmock, J. R.; Elias, D. W.; Beazely, M. A.; Kandepu, N. M. Curr. Med. Chem. 1999, 6, 1125.
  2. Go, M. L.; Wu, X.; Liu, X. L. Curr. Med. Chem. 2005, 12, 483. https://doi.org/10.2174/0929867053363153
  3. Nowakowska, Z. Eur. J. Med. Chem. 2007, 42, 125. https://doi.org/10.1016/j.ejmech.2006.09.019
  4. Sogawa, S.; Nihro, Y.; Ueda, H.; Miki, T.; Matsumoto, H.; Satoh, T. Biol. Pharm. Bull. 1994, 17, 251. https://doi.org/10.1248/bpb.17.251
  5. Nerya, O.; Musa, R.; Khatib, S.; Tamir, S.; Vaya, J. Phytochemistry 2004, 65, 1389. https://doi.org/10.1016/j.phytochem.2004.04.016
  6. Anto, R. J.; Sukumaran, K.; Kuttan, G.; Rao, M. N. A.; Subbaraju, V.; Kuttan, R. Cancer Lett. 1995, 97, 33. https://doi.org/10.1016/0304-3835(95)03945-S
  7. Calliste, C. A.; Le Bail, J. C.; Trouillas, P.; Pouget, C.; Habrioux, G.; Chulia, A. J.; Duroux, J. L. Anticancer Res. 2001, 21, 3949.
  8. Tapiero, H.; Tew, K. D.; Ba, N.; Math, G. Biomed. Pharm. Ther. 2002, 56, 200. https://doi.org/10.1016/S0753-3322(02)00178-6
  9. Cao, G.; Sofic, E.; Prior, R. L. Free Radic. Biol. Med. 1997, 22, 749. https://doi.org/10.1016/S0891-5849(96)00351-6
  10. Burda, S.; Oleszek, W. J. Agric. Food Chem. 2001, 49, 2774. https://doi.org/10.1021/jf001413m
  11. Arora, A.; Nair, M. G.; Strasburg, G. M. Free Radic. Biol. Med. 1998, 24, 1355. https://doi.org/10.1016/S0891-5849(97)00458-9
  12. Pietta, P.-G. J. Nat. Prod. 2000, 63, 1035. https://doi.org/10.1021/np9904509
  13. Dugas, A. J., Jr.; Castaneda-Acosta, J.; Bonin, G. C.; Price, K. L.; Fischer, N. H.; Winston, G. W. J. Nat. Prod. 2000, 63, 327. https://doi.org/10.1021/np990352n
  14. Rezk, B. M.; Haenen, G. R. M. M.; van der Vijgh, W. F. F.; Bast, A. Biochem. Biophys. Res. Commun. 2002, 295, 9. https://doi.org/10.1016/S0006-291X(02)00618-6
  15. De Vincenzo, R.; Ferlini, C.; Distefano, M.; Gaggini, C.; Riva, A.; Bombardelli, E.; Morazzoni, P.; Valenti, P.; Belluti, F.; Ranelletti, F. O.; Mancuso, S.; Scambia, G. Cancer Chemother Pharmacol 2000, 46, 305. https://doi.org/10.1007/s002800000160
  16. Kim, B.-T.; O, K.-J.; Chun, J.-C.; Hwang, K.-J. Bull. Korean Chem. Soc. 2008, 29(6), 1125. https://doi.org/10.5012/bkcs.2008.29.6.1125
  17. Opletalova, V.; Hartl, J.; Patel, A.; Palat, K., Jr.; Buchta, V. Il Farmaco 2002, 57, 135. https://doi.org/10.1016/S0014-827X(01)01187-9
  18. Lopez, S. N.; Castelli, M. V.; Zacchino, S. A.; Dominguez, J. N.; Lobo, G.; Charris-Charris, J.; Cortes, J. C. G.; Ribas, J. C.; Devia, C.; Rodríguez, A. M.; Enriz, R. D. Bioorg. Med. Chem. 2001, 9, 1999. https://doi.org/10.1016/S0968-0896(01)00116-X
  19. Shiotani, S.; Okada, H.; Nakamata, K.; Yamamoto, T.; Sekino, F. Heterocycles 1996, 43, 1031. https://doi.org/10.3987/COM-96-7421
  20. Wang, W.; Zou, J.; Hua, Y.; Liu, H. Zhuanli Shenqing Gongkai Shuomingshu; 2007; p 7.

피인용 문헌

  1. Synthesis and Regioselective Reaction of Some Unsymmetrical Heterocyclic Chalcone Derivatives and Spiro Heterocyclic Compounds as Antibacterial Agents vol.20, pp.12, 2015, https://doi.org/10.3390/molecules201219827
  2. Synthesis of the Hydrazones of 2-((3,5-Di-tert-butyl-4-hydroxybenzyl)thio) acetohydrazide and the Study of their Radical Scavenging Activity by the DPPH Assay and the Computational Method vol.36, pp.11, 2015, https://doi.org/10.1002/bkcs.10553
  3. Synthesis of 4-(2-Amino)ethoxy-3′,4′-dihydroxychalcones and Their Antioxidant and Cytotoxic Effects on Human Tumor Cells vol.36, pp.5, 2015, https://doi.org/10.1002/bkcs.10253
  4. A Potent Tyrosinase Inhibitor, (E)-3-(2,4-Dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with Anti-Melanogenesis Properties in α-MSH and IBMX-Induced B16F10 Melanoma Cells vol.23, pp.10, 2018, https://doi.org/10.3390/molecules23102725
  5. Thiochalcone substituted phthalocyanines for dye-sensitized solar cells: Relation of optical and electrochemical properties for cell performance vol.71, pp.10, 2018, https://doi.org/10.1080/00958972.2018.1468027
  6. -pyrazol-1yl)thiazole derivatives vol.48, pp.11, 2018, https://doi.org/10.1080/00397911.2018.1440600
  7. Palladium(0) catalyzed Suzuki cross-coupling reaction of 2,5-dibromo-3-methylthiophene: selectivity, characterization, DFT studies and their biological evaluations vol.12, pp.1, 2018, https://doi.org/10.1186/s13065-018-0404-7
  8. “1,3-di(thiophen-2-yl) prop-2-en-1-one” kalkon türevinin antifungal, anti-biyofilm ve anti-kanser aktivitelerinin belirlenmesi vol.39, pp.2, 2012, https://doi.org/10.7197/223.v39i29491.316366
  9. Divergent Synthesis and Evaluation of the in vitro Cytotoxicity Profiles of 3,4‐Ethylenedioxythiophenyl‐2‐propen‐1‐one Analogues vol.14, pp.15, 2012, https://doi.org/10.1002/cmdc.201900225