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Synthesis of New N-Phthalimide Substituted Tricyclic Imide Containing Isoxazoline and Bispiro Functional Group as Possible Anti-cancer Agents

Yıl 2018, Cilt: 5 Sayı: 1, 73 - 84, 01.09.2017
https://doi.org/10.18596/jotcsa.338218

Öz

[3+2]-Cycloaddition
reactions of N-phthalimide substituted
tricyclic imide were studied to synthesize their isoxazoline and bispiro
derivatives in excellent yields. All new synthesized compounds have been
characterized by their FTIR, 1H NMR, 13C NMR, GC/MS and
LC/MS (HRMS) analyses.

Kaynakça

  • 1. Kulu I, Goksu G, Sucu BO, Kopruceli A, Ocal N, Kaufmann DE. Synthesis of New Aryl-substituted Tandospirone and Epiboxidine Analogues and Isoxazoline Derivatives. Org Prep Proced Int. 2013;45(1):44-56.
  • 2. Gunkara OT, Sucu BO, Ocal N, Kaufmann DE. Synthesis of new aryl(hetaryl)-substituted tandospirone analogues with potential anxiolytic activity via reductive Heck type hydroarylations. Chem Pap. 2013;67(6):643-9.
  • 3. Gunkara OT, Sucu BO, Guleli M, Ocal N. Synthesis of New Tandospirone Analogues Carrying 1-(3-(Trifluoromethyl)Phenyl)Piperazine. Synthetic Commun. 2014;44(11):1619-28.
  • 4. Wieland S, Fischette CT, Lucki I. Effect of Chronic Treatments with Tandospirone and Imipramine on Serotonin-Mediated Behavioral-Responses and Monoamine Receptors. Neuropharmacology. 1993;32(6):561-73.
  • 5. Mikolajczyk M, Kielbasinski P. Recent Developments in the Carbodiimide Chemistry. Tetrahedron. 1981;37(2):233-84.
  • 6. Conti P, Dallanoce C, De Amici M, De Micheli C, Klotz KN. Synthesis of new Delta(2)-isoxazoline derivatives and their pharmacological characterization as beta-adrenergic receptor antagonists. Bioorgan Med Chem. 1998;6(4):401-8.
  • 7. Kaur K, Kumar V, Sharma AK, Gupta GK. Isoxazoline containing natural products as anticancer agents: A review. Eur J Med Chem. 2014;77:121-33.
  • 8. Ribeiro CJA, Amaral JD, Rodrigues CMP, Moreira R, Santos MMM. Synthesis and evaluation of spiroisoxazoline oxindoles as anticancer agents. Bioorgan Med Chem. 2014;22(1):577-84.
  • 9. Goksu G, Ocal N. 1,3-Dipolar Cycloaddition Reactions of N-Methyl-Substituted Tricyclic Imides. Acta Chim Slov. 2011;58(2):256-61.
  • 10. Gul M, Ocal N. Heck-type hydroarylations and 1,3-dipolar cycloaddition reactions of new tricyclic hydrazones. Can J Chem. 2010;88(4):323-30.
  • 11. Kulu I, Gul M, Gunkara OT, Ocal N. Cycloaddition Reactions of Some Tricyclic Imides. Mini-Rev Org Chem. 2013;10(4):409-18.
  • 12. Gul M, Kulu I, Gunkara OT, Ocal N. Reductive Heck Reactions and [3+2] Cycloadditions of Unsaturated N,N'-Bistricyclic Imides. Acta Chim Slov. 2013;60(1):87-94.
  • 13. Ahrendt KA, Borths CJ, MacMillan DWC. New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction. J Am Chem Soc. 2000;122(17):4243-4.
  • 14. Jen WS, Wiener JJM, MacMillan DWC. New strategies for organic catalysis: The first enantioselective organocatalytic 1,3-dipolar cycloaddition. J Am Chem Soc. 2000;122(40):9874-5.
  • 15. Obst U, Betschmann P, Lerner C, Seiler P, Diederich F, Gramlich V, et al. Synthesis of novel nonpeptidic thrombin inhibitors. Helv Chim Acta. 2000;83(5):855-909.
  • 16. Sebahar PR, Williams RM. The asymmetric total synthesis of (+)- and (-)-spirotryprostatin B. J Am Chem Soc. 2000;122(23):5666-7.
  • 17. Yamamoto Y, Yamamoto S, Yatagai H, Ishihara Y, Maruyama K. Lewis Acid Mediated Reactions of Organocopper Reagents - Entrainment in the Conjugate Addition to Alpha,Beta-Unsaturated Ketones, Esters, and Acids Via the Rcu.Bf3 System. J Org Chem. 1982;47(1):119-26.
  • 18. Kas'yan LI, Tarabara IN, Bondarenko YS, Svyatenko LK, Bondarenko AV. Reactions of 4-amino-4-azatricyclo[5.2.1.0(2,6-endo)]dec-8-ene-3,5-dione with dicarboxylic acid anhydrides. Russ J Org Chem+. 2007;43(7):1014-26.
  • 19. Galvis CEP, Kouznetsov VV. An unexpected formation of the novel 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton during the reaction of furfurylamine with maleimides and their bioprospection using a zebrafish embryo model. Org Biomol Chem. 2013;11(3):407-11.
  • 20. Simunek P, Peskova M, Bertolasi V, Machacek V, Lycka A. Synthesis, NMR and X-ray characterisation of 6-substituted 4-amino-5-aryldiazenyl-1-arylpyridazinium salts. Tetrahedron. 2005;61(34):8130-7.
  • 21. Jung JY, Jung SH, Koh HY, Pae AN, Park WK, Kong JY. Synthesis of piperazinylalkylisoxazoline analogues and their binding affinities for dopamine receptor subtypes. B Korean Chem Soc. 2006;27(11):1861-4.
Yıl 2018, Cilt: 5 Sayı: 1, 73 - 84, 01.09.2017
https://doi.org/10.18596/jotcsa.338218

Öz

Kaynakça

  • 1. Kulu I, Goksu G, Sucu BO, Kopruceli A, Ocal N, Kaufmann DE. Synthesis of New Aryl-substituted Tandospirone and Epiboxidine Analogues and Isoxazoline Derivatives. Org Prep Proced Int. 2013;45(1):44-56.
  • 2. Gunkara OT, Sucu BO, Ocal N, Kaufmann DE. Synthesis of new aryl(hetaryl)-substituted tandospirone analogues with potential anxiolytic activity via reductive Heck type hydroarylations. Chem Pap. 2013;67(6):643-9.
  • 3. Gunkara OT, Sucu BO, Guleli M, Ocal N. Synthesis of New Tandospirone Analogues Carrying 1-(3-(Trifluoromethyl)Phenyl)Piperazine. Synthetic Commun. 2014;44(11):1619-28.
  • 4. Wieland S, Fischette CT, Lucki I. Effect of Chronic Treatments with Tandospirone and Imipramine on Serotonin-Mediated Behavioral-Responses and Monoamine Receptors. Neuropharmacology. 1993;32(6):561-73.
  • 5. Mikolajczyk M, Kielbasinski P. Recent Developments in the Carbodiimide Chemistry. Tetrahedron. 1981;37(2):233-84.
  • 6. Conti P, Dallanoce C, De Amici M, De Micheli C, Klotz KN. Synthesis of new Delta(2)-isoxazoline derivatives and their pharmacological characterization as beta-adrenergic receptor antagonists. Bioorgan Med Chem. 1998;6(4):401-8.
  • 7. Kaur K, Kumar V, Sharma AK, Gupta GK. Isoxazoline containing natural products as anticancer agents: A review. Eur J Med Chem. 2014;77:121-33.
  • 8. Ribeiro CJA, Amaral JD, Rodrigues CMP, Moreira R, Santos MMM. Synthesis and evaluation of spiroisoxazoline oxindoles as anticancer agents. Bioorgan Med Chem. 2014;22(1):577-84.
  • 9. Goksu G, Ocal N. 1,3-Dipolar Cycloaddition Reactions of N-Methyl-Substituted Tricyclic Imides. Acta Chim Slov. 2011;58(2):256-61.
  • 10. Gul M, Ocal N. Heck-type hydroarylations and 1,3-dipolar cycloaddition reactions of new tricyclic hydrazones. Can J Chem. 2010;88(4):323-30.
  • 11. Kulu I, Gul M, Gunkara OT, Ocal N. Cycloaddition Reactions of Some Tricyclic Imides. Mini-Rev Org Chem. 2013;10(4):409-18.
  • 12. Gul M, Kulu I, Gunkara OT, Ocal N. Reductive Heck Reactions and [3+2] Cycloadditions of Unsaturated N,N'-Bistricyclic Imides. Acta Chim Slov. 2013;60(1):87-94.
  • 13. Ahrendt KA, Borths CJ, MacMillan DWC. New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction. J Am Chem Soc. 2000;122(17):4243-4.
  • 14. Jen WS, Wiener JJM, MacMillan DWC. New strategies for organic catalysis: The first enantioselective organocatalytic 1,3-dipolar cycloaddition. J Am Chem Soc. 2000;122(40):9874-5.
  • 15. Obst U, Betschmann P, Lerner C, Seiler P, Diederich F, Gramlich V, et al. Synthesis of novel nonpeptidic thrombin inhibitors. Helv Chim Acta. 2000;83(5):855-909.
  • 16. Sebahar PR, Williams RM. The asymmetric total synthesis of (+)- and (-)-spirotryprostatin B. J Am Chem Soc. 2000;122(23):5666-7.
  • 17. Yamamoto Y, Yamamoto S, Yatagai H, Ishihara Y, Maruyama K. Lewis Acid Mediated Reactions of Organocopper Reagents - Entrainment in the Conjugate Addition to Alpha,Beta-Unsaturated Ketones, Esters, and Acids Via the Rcu.Bf3 System. J Org Chem. 1982;47(1):119-26.
  • 18. Kas'yan LI, Tarabara IN, Bondarenko YS, Svyatenko LK, Bondarenko AV. Reactions of 4-amino-4-azatricyclo[5.2.1.0(2,6-endo)]dec-8-ene-3,5-dione with dicarboxylic acid anhydrides. Russ J Org Chem+. 2007;43(7):1014-26.
  • 19. Galvis CEP, Kouznetsov VV. An unexpected formation of the novel 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton during the reaction of furfurylamine with maleimides and their bioprospection using a zebrafish embryo model. Org Biomol Chem. 2013;11(3):407-11.
  • 20. Simunek P, Peskova M, Bertolasi V, Machacek V, Lycka A. Synthesis, NMR and X-ray characterisation of 6-substituted 4-amino-5-aryldiazenyl-1-arylpyridazinium salts. Tetrahedron. 2005;61(34):8130-7.
  • 21. Jung JY, Jung SH, Koh HY, Pae AN, Park WK, Kong JY. Synthesis of piperazinylalkylisoxazoline analogues and their binding affinities for dopamine receptor subtypes. B Korean Chem Soc. 2006;27(11):1861-4.
Toplam 21 adet kaynakça vardır.

Ayrıntılar

Konular Mühendislik, Kimya Mühendisliği
Bölüm Makaleler
Yazarlar

Omer Tahir Gunkara 0000-0003-3528-5045

Nuket Ocal Bu kişi benim 0000-0002-9062-3783

Yayımlanma Tarihi 1 Eylül 2017
Gönderilme Tarihi 14 Eylül 2017
Kabul Tarihi 31 Ekim 2017
Yayımlandığı Sayı Yıl 2018 Cilt: 5 Sayı: 1

Kaynak Göster

Vancouver Gunkara OT, Ocal N. Synthesis of New N-Phthalimide Substituted Tricyclic Imide Containing Isoxazoline and Bispiro Functional Group as Possible Anti-cancer Agents. JOTCSA. 2017;5(1):73-84.