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Bazı İmidazol ve İmidazo[1,2-a] Pirazin Türevlerinin Antikanser Aktiviteleri Üzerine QSAR Çalışmaları

Year 2015, Volume: 6 Issue: 2, 65 - 73, 30.12.2015

Abstract

Bu çalışmada, antikanser etkiler (Amerika Ulusal Kanser Enstitüsü (NCI) tarafından, 66 kanserli hücrede yapılmış olan büyüme testlerinden alınan Log(1/C) değerleri)  ile bazı fizikokimyasal parametreler (hidrofobik parametreler olarak clogP, p, elektronik parametreler olarak σ, Ŧ, ve sterik parametreler olarak, Es, MR) arasındaki korelasyonlar incelenmiştir. Buna göre, imidazol türevleri için, biyolojik etki ile p, Ŧ, MR parametreleri arasında ve benzer şekilde, imidazo[1,2-a]pirazin türevleri için, biyolojik etki ile clogP, Es parametreleri arasında önemli miktarda korelasyon olduğu rapor edilmiştir.

Anahtar Kelimeler: İmidazo[1,2-a]pirazin, pirazino[1,2-a]benzimidazol, antikanser etki, kantitatif yapı-etki ilişkileri (QSAR), Hansch analiz metodu

References

  • Adamczyk M., Akireddy S. R., Johnson D. D., Mattingly P. G., Pan Y., & Reddy R. E. (2003). Synthesis of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones and their chemiluminescent properties. Tetrahedron, 59, 8129-8142.
  • Barraclough P., Black J. W., Cambridge D., Gerskowitsch V. P., Giles H., Glen R. C., Hull R. A. D., Iyer R., & King W. R. (1993). Synthesis and pharmacological properties of BW315C and other inotropic 2-arylimidazo[1,2-a]pyrazines. Bioorganic and Medicinal Chemistry Letters, 3, 509-514.
  • Boyd M. R. (1989). Status of the NCI preclinical antitumor drug discovery screen. Cancer: Principles and Practice of Oncology Updates, 3(10), 1-12.
  • Brown D. J. (2001). The pyrazines, Chem. Heterocycl. Compd. (Suppl. I). Canada: John Wiley & Sons Inc.
  • Contour-Galcera M. O., Poitout L., Moinet C., Morgan B., Gordon T., Roubert P., & Thurieau C. (2001). Synthesis of imidazopyrazines as ligands for the human somatostatin receptor subtype 5. Bioorganic and Medicinal Chemistry Letters, 11, 741-745.
  • Demirayak Ş., Abu Mohsen U., & Karaburun A. Ç. (2002). Synthesis and anticancer and anti-HIV testing of some pyrazino[1,2-a]benzimidazole derivatives. European Journal of Medicinal Chemistry, 37, 255-260.
  • Demirayak S., & Kayagil I. (2005). Synthesis of some 6,8-Diarylimidazo[1,2-a]pyrazine Derivatives by Using Either Reflux or Microwave Irradiation Method and Investigation of Their Anticancer Activities. Journal of Heterocyclic Chemistry, 42, 319-325.
  • Demirayak S., Kayagil I., & Yurttas L. (2011). Microwave supported synthesis of some novel 1,3-Diarylpyrazino[1,2-a]benzimidazole derivatives and investigation of their anticancer activities. European Journal of Medicinal Chemistry, 46, 411-416.
  • Hansch C., & Leo A. (1995). Exploring QSAR, fundamentals and applications in chemistry and biology. Washington, USA: ACS Press.
  • Hansch C., Leo A., & Hoekman D. (1995). Exploring QSAR, hydrophobic, electronic, and steric constants. Washington, USA: ACS Press.
  • Hansch C., Leo A., Unger S. H., Nikaitani K. H. K. D., & Lien E. J. (1973). Aromatic substituent constants for structure activity correlations. Journal of Medicinal Chemistry, 16, 1207-1216.
  • Hansch C., Rockwell S. D., Jow P. Y. C., Leo A., & Steller E. E. (1977). Substituent constants for correlation analysis. Journal of Medicinal Chemistry, 20, 304-306.
  • Kayağil İ., & Demirayak Ş. (2011). Synthesis of some 2,3,6,8-tetraarylimidazo[1,2-a]pyrazine derivatives by using either reflux or microwave irradiation method, and investigation their anticancer activities. Turkish Journal of Chemistry, 35, 13-24.
  • Kubinyi H. (1993). QSAR: hansch analysis and related approaches. New York, USA: VCH Publisher.
  • Leo A., Hansch C., & Elkins D. (1971). Partition coefficients and their uses. Chemical Reviews, 71, 525-616.
  • Leo A., Jow P. Y. C., Silipo C., & Hansch C. (1975). Calculation of hydrophobic constant (log P) from  and f constants. Journal of Medicinal Chemistry, 18, 865-868.
  • Mccapra F., & Roth M. (1972). Cyclization of a dehydropeptide derivative. Model for cypridina luciferin biosynthesis. Journal of the Chemical Society, Chemical Communications, 15, 894-895.
  • Prevost C., Coulomb H., Lavergne O., Lanco C., & Teng B. P. (2003). Patent No. WO 2002096348 A2.
  • Silverman R. B. (2004). The organic chemistry of drug design and drug action (2nd Ed.). California, USA: Elsevier Academic Press.
  • Taft R. W. (1952). Polar and steric substituent constants for aliphatic and o-benzoate groups from rates of esterification and hydrolysis of esters. Journal of American Chemical Society, 74, 3120-3128.
  • Thurieau C. A., Poitout L. F., Galcera M. O., Gordon T. G., Morgan B., & Moinet C. P. (2000). Patent No. WO 1999064401 A2.
  • Thurieau C. A., Poitout L. F., Galcera M. O., Gordon T., Morgan B. A., Moinet C. P., & Bigg D. (2002). Patent No. WO 2002010140 A2.
  • Toshio G., Shoji I., & Sumi S. (1968). Cypridina bioluminescence. IV. Synthesis and chemiluminescence of 3,7-dihydroimidazo[1,2-a]pyrazine-3-one and its 2-methyl derivative. Tetrahedron Letters, 36, 3873-3876.

QSAR Studies on Anticancer Activities of Some Imidazole and Imidazo [1,2-a] Pyrazine Derivatives

Year 2015, Volume: 6 Issue: 2, 65 - 73, 30.12.2015

Abstract

Bu çalışmada, antikanser etkiler (Amerika Ulusal Kanser Enstitüsü (NCI) tarafından, 66 kanserli hücrede yapılmış olan büyüme testlerinden alınan Log(1/C) değerleri) ile bazı fizikokimyasal parametreler (hidrofobik parametreler olarak clogP, , elektronik parametreler olarak σ, Ŧ, ve sterik parametreler olarak, Es, MR) arasındaki korelasyonlar incelenmiştir. Buna göre, imidazol türevleri için, biyolojik etki ile , Ŧ, MR parametreleri arasında ve benzer şekilde, imidazo[1,2-a]pirazin türevleri için, biyolojik etki ile clogP, Esparametreleri arasında önemli miktarda korelasyon olduğu rapor edilmiştir

References

  • Adamczyk M., Akireddy S. R., Johnson D. D., Mattingly P. G., Pan Y., & Reddy R. E. (2003). Synthesis of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones and their chemiluminescent properties. Tetrahedron, 59, 8129-8142.
  • Barraclough P., Black J. W., Cambridge D., Gerskowitsch V. P., Giles H., Glen R. C., Hull R. A. D., Iyer R., & King W. R. (1993). Synthesis and pharmacological properties of BW315C and other inotropic 2-arylimidazo[1,2-a]pyrazines. Bioorganic and Medicinal Chemistry Letters, 3, 509-514.
  • Boyd M. R. (1989). Status of the NCI preclinical antitumor drug discovery screen. Cancer: Principles and Practice of Oncology Updates, 3(10), 1-12.
  • Brown D. J. (2001). The pyrazines, Chem. Heterocycl. Compd. (Suppl. I). Canada: John Wiley & Sons Inc.
  • Contour-Galcera M. O., Poitout L., Moinet C., Morgan B., Gordon T., Roubert P., & Thurieau C. (2001). Synthesis of imidazopyrazines as ligands for the human somatostatin receptor subtype 5. Bioorganic and Medicinal Chemistry Letters, 11, 741-745.
  • Demirayak Ş., Abu Mohsen U., & Karaburun A. Ç. (2002). Synthesis and anticancer and anti-HIV testing of some pyrazino[1,2-a]benzimidazole derivatives. European Journal of Medicinal Chemistry, 37, 255-260.
  • Demirayak S., & Kayagil I. (2005). Synthesis of some 6,8-Diarylimidazo[1,2-a]pyrazine Derivatives by Using Either Reflux or Microwave Irradiation Method and Investigation of Their Anticancer Activities. Journal of Heterocyclic Chemistry, 42, 319-325.
  • Demirayak S., Kayagil I., & Yurttas L. (2011). Microwave supported synthesis of some novel 1,3-Diarylpyrazino[1,2-a]benzimidazole derivatives and investigation of their anticancer activities. European Journal of Medicinal Chemistry, 46, 411-416.
  • Hansch C., & Leo A. (1995). Exploring QSAR, fundamentals and applications in chemistry and biology. Washington, USA: ACS Press.
  • Hansch C., Leo A., & Hoekman D. (1995). Exploring QSAR, hydrophobic, electronic, and steric constants. Washington, USA: ACS Press.
  • Hansch C., Leo A., Unger S. H., Nikaitani K. H. K. D., & Lien E. J. (1973). Aromatic substituent constants for structure activity correlations. Journal of Medicinal Chemistry, 16, 1207-1216.
  • Hansch C., Rockwell S. D., Jow P. Y. C., Leo A., & Steller E. E. (1977). Substituent constants for correlation analysis. Journal of Medicinal Chemistry, 20, 304-306.
  • Kayağil İ., & Demirayak Ş. (2011). Synthesis of some 2,3,6,8-tetraarylimidazo[1,2-a]pyrazine derivatives by using either reflux or microwave irradiation method, and investigation their anticancer activities. Turkish Journal of Chemistry, 35, 13-24.
  • Kubinyi H. (1993). QSAR: hansch analysis and related approaches. New York, USA: VCH Publisher.
  • Leo A., Hansch C., & Elkins D. (1971). Partition coefficients and their uses. Chemical Reviews, 71, 525-616.
  • Leo A., Jow P. Y. C., Silipo C., & Hansch C. (1975). Calculation of hydrophobic constant (log P) from  and f constants. Journal of Medicinal Chemistry, 18, 865-868.
  • Mccapra F., & Roth M. (1972). Cyclization of a dehydropeptide derivative. Model for cypridina luciferin biosynthesis. Journal of the Chemical Society, Chemical Communications, 15, 894-895.
  • Prevost C., Coulomb H., Lavergne O., Lanco C., & Teng B. P. (2003). Patent No. WO 2002096348 A2.
  • Silverman R. B. (2004). The organic chemistry of drug design and drug action (2nd Ed.). California, USA: Elsevier Academic Press.
  • Taft R. W. (1952). Polar and steric substituent constants for aliphatic and o-benzoate groups from rates of esterification and hydrolysis of esters. Journal of American Chemical Society, 74, 3120-3128.
  • Thurieau C. A., Poitout L. F., Galcera M. O., Gordon T. G., Morgan B., & Moinet C. P. (2000). Patent No. WO 1999064401 A2.
  • Thurieau C. A., Poitout L. F., Galcera M. O., Gordon T., Morgan B. A., Moinet C. P., & Bigg D. (2002). Patent No. WO 2002010140 A2.
  • Toshio G., Shoji I., & Sumi S. (1968). Cypridina bioluminescence. IV. Synthesis and chemiluminescence of 3,7-dihydroimidazo[1,2-a]pyrazine-3-one and its 2-methyl derivative. Tetrahedron Letters, 36, 3873-3876.
There are 23 citations in total.

Details

Primary Language English
Journal Section Research Paper
Authors

İsmail Kayağil

Şeref Demirayak

Publication Date December 30, 2015
Published in Issue Year 2015 Volume: 6 Issue: 2

Cite

APA Kayağil, İ., & Demirayak, Ş. (2015). Bazı İmidazol ve İmidazo[1,2-a] Pirazin Türevlerinin Antikanser Aktiviteleri Üzerine QSAR Çalışmaları. Mehmet Akif Ersoy Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 6(2), 65-73.