한국응용과학기술학회지 (Journal of the Korean Applied Science and Technology)

  • 제27권1호
  • /
  • Pages.20-28
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  • 2010
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  • 1225-9098(pISSN)
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  • 2288-1069(eISSN)
한국응용과학기술학회 (The Korean Society of Applied Science and Technology)
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Quinazolinylmethoxybenzene 유도체 합성 및 흑색종 세포증식 저해효능

Synthesis and Antiproliferative Activity of Quinazolinylmethoxybenzene Derivatives against Melanoma Cell Line

  • 이준상 (한국과학기술연구원 바이오소재센터) ;
  • 유경호 (한국과학기술연구원 바이오소재센터)
  • Lee, Jun-Sang (Biomaterials Center, Korea Institute of Science and Technology) ;
  • Yoo, Kyung-Ho (Biomaterials Center, Korea Institute of Science and Technology)
  • 투고 : 2010.01.28
  • 심사 : 2010.03.10
  • 발행 : 2010.03.30
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초록

Melanoma is the most aggressive form of skin cancer and is the fastest growing type of cancer in the United States. We report here the synthesis of a novel series of quinazolinylmethoxybenzene derivatives 1a-c and their antiproliferative activities against A375 human melanoma cell line. Among them, urea compound 1a ($IC_{50}\;=\;4.8\;{\mu}M$) having 4-chloro-3-trifluoromethylphenyl moiety showed superior antiproliferative activity to Sorafenib ($IC_{50}\;=\;5.5\;{\mu}M$) as a reference compound. These results will helpful for designing structure of a therapeutic agent for the treatment of melanoma.

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참고문헌

  1. B. J. Druker and N. B. Lydon, Lessons Learned from the Development of an Abl Tyrosine Kinase Inhibitor for Chronic Myelogenous Leukemia, J. Clin. Invest, 105, 3 (2000). https://doi.org/10.1172/JCI9083
  2. D. Raben, B. A. Helfrich, D. Chan, G. Johnson, and P. A. Bunn, Jr., ZD1839, A Selective Epidermal Growth Factor Receptor Tyrosine Kinase Inhibitor Alone and in Combination with Radiation and Chemotherapy as a New Therapeutic Strategy in Non-small Cell Lung Cancer, Semin. Oncol., 29 (Supplement 4), 37 (2002). https://doi.org/10.1053/sonc.2002.31521
  3. R. Perez-Soler, A. Chachoua, L. A. Hammond, E. K. Rowinsky, M. Huberman, D. Karp, J. Rigas, G. M. Clark, P. Santabarbara, and P. Bonomi, Determinants of Tumor Response and Survival with Erlotinib in Patients with Non-Small-Cell Lung Cancer, J. Clin. Oncol., 22, 3238 (2004). https://doi.org/10.1200/JCO.2004.11.057
  4. C. Garbe, A. Hauschild, M. Volkenandt, D. Schadendorf, W. Stolz, U. Reinhold, R. D. Kortmann, C. Kettelhack, B. Frerich, U. Keilholz, R. Dummer, G. Sebastian, W. Tilgen, G. Schuler, A. Mackensen, and R. Kaufmann, Evidence and Interdisciplinary Consense-based German Guidelines: Diagnosis and Surveillance of Melanoma, Melanoma Res., 17, 393 (2007). https://doi.org/10.1097/CMR.0b013e3282f05039
  5. J. A. Carlson, J. S. Ross, A. Slominski, G. Linette, J. Mysliborski, J. Hill, and M. Mihm, Jr., Molecular Diagnostics in Melanoma, J. Am Acad. Dermatol., 52, 743 (2005). https://doi.org/10.1016/j.jaad.2004.08.034
  6. A. C. Buzaid and C. M. Anderson, The Changing Prognosis of Melanoma, Curr. Oncol. Rep., 2, 322 (2000). https://doi.org/10.1007/s11912-000-0025-9
  7. M. R. Middleton, J. J. Grob, N. Aaronson, G. Fierlbeck, W. Tilgen, S. Seiter, M. Gore, S. Aamdal, J. Cebon, A. Coates, B. Dreno, M. Henz, D. Schadendorf, A. Kapp, J. Weiss, U. Fraass, P. Statkevich, M. Muller, and N. Thatcher, Randomized Phase III Study of Temozolomide versus Dacarbazine in the Treatment of Patients with Advanced Metastatic Malignant Melanoma, J. Clin. Oncol., 18, 158 (2008).
  8. A. Y. Bedikian, M. Millward, H. Pehamberger, R. Conry, M. Gore, U. Trefzer, A. C. Pavlick, R. DeConti, E. M. Hersh, P. Hersey, J. M. Kirkwood, and F. G. Haluska, B치-2 Antisense (oblimersen sodium) Plus Dacarbazine in Patients With Advanced Melanoma: The Oblimersen Melanoma Study Group, J. Clin. Oncol., 24, 4738 (2006). https://doi.org/10.1200/JCO.2006.06.0483
  9. D. H. Lawson, Choices in Adjuvant Therapy of Melanoma, Cancer Control, 12, 236 (2005). https://doi.org/10.1177/107327480501200405
  10. S. A. Rosenburg, M. T. Lotze, J. C. Yang, P. M. Aebersold, W. M. Linehan, C. A. Seipp, and D. E. White, Experience with the Use of High Dose Interleukin-2 in the Treatment of 652 Cancer Patients, Ann. Surg., 210, 474 (1989). https://doi.org/10.1097/00000658-198910000-00008
  11. M. B. Atkins, M. T. Lotze, J. P. Dutcher, R. I. Fisher, G. Weiss, K. Margolin, J. Abrams, M. Sznol, D. Parkinson, M. Hawkins, C. Paradise, L. Kunkel, and S. A. Rosenberg, High-dose Recombinant Interleukin 2 Therapy for Patients with Metastatic Melanoma: Analysis of 270 Patients Treated between 1985 and 1993, J. Clin. Oncol., 17, 2105 (1999). https://doi.org/10.1200/JCO.1999.17.7.2105
  12. C. M. Anderson, A. C. Buzaid, and S. S. Legha, Systemic Treatments for Advanced Cutaneous Melanoma, Oncology, 9, 1149 (1995).
  13. L. Serrone, M. Zeuli, F. M. Sega, and F. Cognetti, Dacarbazine-based Chemotherapy for Metastatic Melanoma: Thirty-year Experience Overview, J. Exp. Clin. Cancer Res., 19, 21 (2000).
  14. W. S. Fletcher, D. S. Daniels, V. K. Sondak, B. Dana, R. Townsend, H. E. Hynes, L. F. Hutchins, and J. R. Pancoast, Evaluation of Cisplatin and DTIC in Inoperable Stage III and IV Melanoma, Am. J. Clin. Oncol., 16, 359 (1993). https://doi.org/10.1097/00000421-199308000-00018
  15. B. S. Nam and K. H. Yoo, Synthesis of New Benzaminoquinoline Derivatives with Antiproliferative Activity against Melanoma Cell Line, J. Kor. Oil Chem. Soc, 26, 297 (2009).
  16. V. Kumar, G. Bhargava, P. D. Dey, and M. P. Mahajan, A Convenient Route to Biologically Important Quinazolines Using N-Arylamino-1,3-diazabuta-1,3-dienes, Curr. Med Chem, 11, 2549 (2004). https://doi.org/10.2174/0929867043364423
  17. G.-Y. Li, X.-H. Qianc, S.-G. Yan, J.-N. Cui, Q.-C. Huang, R. Zhang, F. -Y. Liu, and D.-W. Cui, Synthesis and Biological Activity of Novel Symmetrical Bis-2-phenyliminothiazolidine Derivatives, J. Med Chem, 48, 3354 (2005). https://doi.org/10.1021/jm049061o
  18. L. V. Dubey and I. V. Dubey, Side Reactions of Onium Coupling Reagents BOP and HBTU in the Synthesis of Silica Polymer Supports, Ukr. Bioorg. Acta, 1, 13 (2005).
  19. S. M. Wilhelm, L. Adnane, P. Newell, A. Villanueva, J. M. Llovet, and M. Lynch, Preclinical Overview of Sorafenib, a Multikinase Inhibitor that Targets Both Raf and VEGF and PDGF Receptor Tyrosine Kinase Signaling, Mol. Cancer Ther., 7, 3129 (2008). https://doi.org/10.1158/1535-7163.MCT-08-0013