PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Tytuł artykułu

Próby aktywowania grupy karboksylowej kwasu 3-amino-1Hpirazolo-5-karboksylowego metodą azydkową

Treść / Zawartość
Identyfikatory
Warianty tytułu
Attempts of activating carboxylic group of 3-amine-1-Hpyrazole-5-carboxylic acid using azide method
Języki publikacji
PL EN
Abstrakty
PL
Opracowano metodę łączenia 3-acetamido-5-karboksy-1H-pirazolu od C- końca z aminokwasem białkowym, bez konieczności ochrony bocznych grup funkcyjnych pierścienia pirazolowego z wykorzystaniem aktywacji azydkowej. W modelowej reakcji zsyntezowano ester metylowy N-(3-acetamido-5-karbonylo-1H-pirazolo)glicyny.
EN
The method was developed for linking 3-acetamido-5-carboxy-1H-pyrazole with protein amino acid from C-end without necessity to protect side functional groups of pyrazole ring by means of azide activation. In the model reaction N-(3-acetamido-5-carbonyl-1Hpyrazole) glycine methyl ester was synthesized.
Czasopismo
Rocznik
Strony
296--303
Opis fizyczny
Bibliogr.36 poz., rys.
Twórcy
  • Zakład Chemii Organicznej, Wydział Chemii, Uniwersytet Opolski, Opole
  • Zakład Chemii Organicznej, Wydział Chemii, Uniwersytet Opolski, Opole
Bibliografia
  • 1. Elguero J. [w:] “Comprehensive Heterocyclic Chemistry” The Structure, Reactions,Synthesis and Uses of Heterocyclic Compounds, red. A. R. Katritzky, Ch. W. Ress, Pergamon Press 1984, 5, 291–293, 294–295, 302–303.
  • 2. Adesanya SA, Nia R., et al.: Pyrazole alkaloids from Newbouldia laevis. Phytochem. 1994, 35,1053–1055.
  • 3. Parameswaran P.S., Naik, C.G., Hegde, V.R.: Secondary metabolites from the sponge Tedania anhelans: Isolation and characterization of two novel pyrazole acids and other metabolites. J. Nat. Prod. 1997, 60, 802–803.
  • 4. Mishra L.C., Singh B.B., Dagenais S.: Scientific basis for the therapeutic use of Withania somnifera (ashwagandha): a review. Altern. Med. Rev. 2000, 5, 334–346.
  • 5. Gupta G.L., Rana A.C.: Withania somnifera (Ashwagandha): a review. Phcog. Rev. 2007, 1, 129–136.
  • 6. Dewangan D., Kumar et al.: Pyrazole: Their Chemistry and Pharmacological Potentials: A Review. CPR 1(4), 2011, 369–377.
  • 7. Rostom, Sh. A. F., Shalaby M. A, El- Demellawy M. A.: Polysubstituted pyrazoles, part 5. Synthesis of new 1-(4-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylic acid hydrazide analogs and some derived ring systems. A novel class of potential antitumor and anti-HCV agents. Europ. J. Med. Chem. 2003, 38, 959–974.
  • 8. Ishida J., Ohtsu H., et al.: Antitumor Agents. Part 214:Synthesis and Evaluation of Curcumin Analogues as Cytotoxic Agent. Bioorg. Med. Chem. 2002, 10, 3481–3487.
  • 9. El- Gaby M. S. A, Atalla A. A., Gaber et al.: Studies on aminopyrazoles: antibacterial activity of some novel pyrazolo[1,5-a]pyrimidines containing sulfonamide moieties. Il Farmaco 2000, 55, 596–602.
  • 10. Kaymakçioğlu B. K., Rollas S.: Synthesis, characterization and evaluation of antituberculosis activity of some hydrazones. Il Farmaco 2002, 57 595–599.
  • Bibliografia załącznikowa
  • (wykaz literatury) 1. Elguero J. [w:] “Comprehensive Heterocyclic Chemistry” The Structure, Reactions,Synthesis and Uses of Heterocyclic Compounds, red. A. R. Katritzky, Ch. W. Ress, Pergamon Press 1984, 5, 291–293, 294–295, 302–303.
  • 2. Adesanya SA, Nia R., et al.: Pyrazole alkaloids from Newbouldia laevis. Phytochem. 1994, 35,1053–1055.
  • 3. Parameswaran P.S., Naik, C.G., Hegde, V.R.: Secondary metabolites from the sponge Tedania anhelans: Isolation and characterization of two novel pyrazole acids and other metabolites. J. Nat. Prod. 1997, 60, 802–803.
  • 4. Mishra L.C., Singh B.B., Dagenais S.: Scientific basis for the therapeutic use of Withania somnifera (ashwagandha): a review. Altern. Med. Rev. 2000, 5, 334–346.
  • 5. Gupta G.L., Rana A.C.: Withania somnifera (Ashwagandha): a review. Phcog. Rev. 2007, 1, 129–136.
  • 6. Dewangan D., Kumar et al.: Pyrazole: Their Chemistry and Pharmacological Potentials: A Review. CPR 1(4), 2011, 369–377.
  • 7. Rostom, Sh. A. F., Shalaby M. A, El- Demellawy M. A.: Polysubstituted pyrazoles, part 5. Synthesis of new 1-(4-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylic acid hydrazide analogs and some derived ring systems. A novel class of potential antitumor and anti-HCV agents. Europ. J. Med. Chem. 2003, 38, 959–974.
  • 8. Ishida J., Ohtsu H., et al.: Antitumor Agents. Part 214:Synthesis and Evaluation of Curcumin Analogues as Cytotoxic Agent. Bioorg. Med. Chem. 2002, 10, 3481–3487.
  • 9. El- Gaby M. S. A, Atalla A. A., Gaber et al.: Studies on aminopyrazoles: antibacterial activity of some novel pyrazolo[1,5-a]pyrimidines containing sulfonamide moieties. Il Farmaco 2000, 55, 596–602.
  • 10. Kaymakçioğlu B. K., Rollas S.: Synthesis, characterization and evaluation of antituberculosis activity of some hydrazones. Il Farmaco 2002, 57 595–599.
  • 11. Karrouchi K., Charkaoui Y., et al.: Synthesis, characterization and preliminary biological activity of some new pyrazole carbohydrazide derivatives. J. Chem.Pharm. Res. 2013, 5, 1–6.
  • 12. Unverferth K., Engels J., et al.: Synthesis, anticonvulsant activity, and structure-activity relationships of sodium channel blocking 3-aminopyrroles.J. Med.Chem.1998, 41, 63–73.
  • 13. Minchon V., Hervē du Penhoat C., et al.: Preparation, structural analysis and anticonvulsant activity of 3- and 5-aminopyrazole N-benzoyl derivatives Europ. J. Med. Chem. 1995, 30, 147–155.
  • 14. Lankau H.- J., Menzer M., Rostock et al.: 3-amino- and 5-aminopyrazoles with anticonvulsant activity Arch. Pharm. 1999, 332, 219–221.
  • 15. Kingsbury W.D., Gyurik R.J., et al.: Synthesis of 1- and 2-substituted indazoles as anthelmintic agents. J. Med. Chem. 1976, 19, 839–840.
  • 16. Kordik Ch. P., Chi Luo et al.: Pyrazolecarboxamide human neuropeptide Y5 receptor ligands with in vivo antifeedant activity. Bioorg. Med.l Chem. Lett. 2001, 11, 2287–2290.
  • 17. Wang A. X., Xie Q et al.: Synthesis and immunosuppressant activity of pyrazole carboxamides. Bioorg. Med. Chem. Lett. 1998, 8, 2787–2792.
  • 18. Ji Ram V., Nath M., Saraswat B., Patnaik G. K.: Amino azoles and azolo-azines as potential hepatoprotectants: Part III. Bioorg. Med. Chem. Lett. 1995, 5, 1537–1540.
  • 19. Bauer V.J., Dalalian H.P., Fanshawe W.J., Safir S.R.: 4-[3(5)-Pyrazolyl] pyridinium salts: A new class of hypoglycemic agents. J. Med. Chem. 1968, 11, 981–984.
  • 20. Cottineau B., Toto P., Marot Ch., Pipaud A., Chenault J.: Synthesis and hypoglycemic evaluation of substituted pyrazole-4-carboxylic acids. Bioorg. Med. Chem. Lett. 2002, 12, 2105–2108.
  • 21. Shrof J.R., Bandurco V., Desai R., Kobrin S., Cervoni P.: Chemistry and Hypoglycemic Activity of Benzimidoylpyrazoles J. Med. Chem., 1981, 24, 1521–1525.
  • 22. Skinner P.J.,. Webb P.J, et al.: 5-N,N-Disubstituted 5-aminopyrazole-3-carboxylic acids are highly potentagonists of GPR109. Bioorg. Med. Chem. Lett. 2009, 19 4207–4209.
  • 23. Nguyen D. H., Szewczyk J. W., Baird E.E., Dervan P. B.: Alternative heterocycles for DNA recognition: an N-methylpyrazole/N-methylpyrrole pair specifies for A.T/T.A base pairs. Bioorg. Med. Chem. 2001, 9, 7–17.
  • 24. Kirsten Ch.N., Schrader T.H.: Intermolecular -Sheet Stabilisation with Aminopyrazoles. J. Am. Chem. Soc. 1997, 119, 12061–12068.
  • 25. Rzepecki P., Wehner M., Molt O., Zadmard R., Harms K., Schrader T.: Aminopyrazole Oligomers for ß-Sheet Stabilization of Peptides. Synthesis 2003, 12, 1815–1826.
  • 26. Rzepecki P., Nagel-Steger L., et al.: Prevention of Alzheimer’s associated Aß aggregation by rationally designed nonpeptidic ß-sheet ligands. J. Biol. Chem. 2004, 279, 47497–47505
  • 27. Rzepecki P., Gallmeier H., Geib N., Cernovska K., König B., Schrader T.New heterocyclic ß-sheet ligands with peptidic recognition elements. J. Org. Chem. 2004, 69, 5168–5178.
  • 28. Cernovská K., Kemter M., Gallmeier H.-Ch., Rzepecki P., Schrader T., König.: PEG-supported Synthesis of Pyrazole Oligoamides with Peptide ß-Sheet Affinity Org. Biomol. Chem. 2004, 2, 1603–1611.
  • 29. Rzepecki P., Schrader T.: ß-Sheet Ligands in Action – KLVFF-Recognition by Aminopyrazole Hybrid Receptors in Water. J. Am. Chem. Soc. 2005, 127, 3016–3025.
  • 30. Rzepecki P., Geib N., Peifer M., Biesemeier F., Schrader T.: Synthesis and Binding studies of Alzheimer-Ligands on Solid Support. J. Org. Chem. 2007, 72, 3614 -3624.
  • 31. Fricke H., Gerlach A., Unterberg C., Wehner M., Schrader T., Gerhards M.: Interactions of Small Protected Peptides with Aminopyrazole Derivatives:The Efficiency of capping a ß-Sheet Model in the Gas Phase. Angew. Chem. 2009, 48, 900–904.
  • 32. Hochdörffer K., März-Berberich J., et al.: Rational Design of ß-Sheet Ligands against Aß42-induced toxicity. J. Am. Chem. Soc. 2011, 133, 4348–4358.
  • 33. Kroth H., Ansaloni A., Varisco Y., Jan A. et al.: Discovery and Structure Activity Relationship of Small Molecule Inhibitors of Toxic ß-Amyloid-42 Fibril Formation., J. Biol. Chem. 2012, 287, 34786–34800.
  • 34. Patent PL 212788 B1 „Sposób wytwarzania alkilo 3-(acyloamino)-1H-pirazolo-5-karboksylanu” (2012) Anna Kusakiewicz-Dawid, Łukasz Górecki, Elżbieta Masiukiewicz, Barbara Rzeszotarska, Polska.
  • 35. Kusakiewicz-Dawid A., Górecki Ł., Masiukiewicz E., Rzeszotarska B.: Susceptibility of Methyl 3-Amino-1H-pyrazole-5-carboxylate to Acylation Synth. Comm. 2009, 23, 4122–4132.
  • 36. Lutz J., Musiol H. J., Moroder L., Houben-Weyl Methods of Organic Chemistry, Ed. M. Goodman, Thieme Stuttgart – New York E22, 2002, 427.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-3bd91197-5cac-4332-9061-1ae8eda275a5
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.