Advertisement

Medicinal Chemistry Research

, Volume 20, Issue 1, pp 125–129 | Cite as

2-Substituted-8-methyl-3,6-dihydroimidazo[4,5-c]pyrazolo[3,4-e]pyridazine as an anti-inflammatory agent

  • Ashish Kumar Tewari
  • Rashmi Dubey
  • Anil Mishra
Original Research

Abstract

A series of 8-methyl-2-substituted-3,6-dihydroimidazo[4,5-c]pyrazolo[3,4-e]pyridazine compounds have been synthesized in the present investigation utilizing Philips condensation (Philips, J Chem Soc 2393–2399, 1928). The anti-inflammatory activity of the synthesized compounds was evaluated using a carrageenin rat model.

Keywords

8-Methyl-2-substituted-3,6-dihydroimidazo[4,5-c]pyrazolo[3,4-e]pyridazine Anti-inflammatory Philips condensation 

Notes

Acknowledgment

The authors acknowledge the help of RSCI, CDRI Lucknow for providing the spectral analysis. Financial assistance from UGC India grant no F.31-139/2005 (SR), India is also gratefully acknowledged.

References

  1. Avasthi K, Tewari A, Rawat DS, Sharon A, Prakash R, Maulik PR (2002) A stacked pyrazolo[3,4-d]pyrimidine-based flexible molecule: the effect of a bulky benzyl group on intermolecular stacking in comparison with methyl and ethyl groups. Acta Crystallogr Sect C 58:494–496CrossRefGoogle Scholar
  2. Avasthi K, Farooq SM, Tewari AK, Sharon A, Maulik PR (2003) Intermolecular stacking in pyrazolo[3,4-d]pyrimidine-based pentamethylene-linked flexible molecules. Acta Crystallogr Sect C 59:o42–o45CrossRefGoogle Scholar
  3. Buttle GAH, D’Arcy PF, Howard EM, Kellett DN (1957) Plethysmometric measurement of swelling in the feet of small laboratory animals. Nature 179:629CrossRefPubMedGoogle Scholar
  4. Caronna S, Migliara O, Petruso S (1986) Synthesis of pyrazole(3,4-a)pyridazine derivatives. Bull Chem Farm 125:114–116Google Scholar
  5. Deeb A, Said SA (1990) Studies on polyazaindenes synthesis of several new condensed pyridazine derivatives. Collect Czech Chem Commun 55:2795CrossRefGoogle Scholar
  6. Deeb A, Said SA, Homed MM Yasine F (1990) J Chim Soc (Taipei) 37 287Google Scholar
  7. Deeb A, Bayoumy B, Essawy AE, Fikry R (1991) Pyridazine derivatives and related compounds part 5. Pyrazolo[3,4-c]pyridazine: synthesis and some reactions. Heterocycles 32:895–900CrossRefGoogle Scholar
  8. Druey J (1958) Angew Chem 70:5CrossRefGoogle Scholar
  9. Hendrickson JB, Rees R, Templeton JF (1964) A new general heterocycle synthesis; use of acetylenedicarboxylic esters. J Am Chem Soc 86:107–111CrossRefGoogle Scholar
  10. Huisgen R, Gotthardt H, Groshey R (1968) Chem Ber 101:1062Google Scholar
  11. Kasuga K, Hirobe M, Okamoto T (1974) Reaction of N-aminopyridinium derivatives. XIII. Syntheses of pyrazolodiazines by cyclization of N-aminodiazinium salts. Chem Pharm Bull 22:1814PubMedGoogle Scholar
  12. Kobayashi Y, Kutsuma T, Morinaga K (1971) Studies on the reactions of heterocyclic compounds. V. Syntheses of diazinium ylides and their conversion to azaindolizines. Chem Pharm Bull (Tokyo) 19:2106–2115Google Scholar
  13. Kurihara T, Uno T, Sakomoto Y (1980) Reaction of ethyl 3-thoxymethylene-2,4-dioxovalerate with monosubstituted hydrazines. J Heterocycl Chem 17:231–233CrossRefGoogle Scholar
  14. Olayemi JO, Ajaiyeoba EO (2007) Short communication—anti-inflammatory studies of yam (Dioscorea esculenta) extract on wistar rats. Afr J Biotechnol 6:1913–1915Google Scholar
  15. Philips MA (1928) The formation of 2-substituted benziminazoles. J Chem Soc 2393–2399. doi: 10.1039/JR9280002393
  16. Potts KT, Elliott AJ (1973) o-Dibenzoyl heterocycles via cycloaddition reactions. Convenient route to fused pyridazine systems. J Org Chem 38:1769CrossRefGoogle Scholar
  17. Potts KT, Roy DN (1968) 1,3-Dipolar cyclo-addition of mesoionic anhydro-2-aryl-5-hydroxy-3-methylthiazolium hydroxides. Chem Commun 536:1061–1062Google Scholar
  18. Seada M, Fawzy MM, Johine H, Magid MA, Saad RR (1989) J Chin Soc (Taipei) 36:241Google Scholar
  19. Segura L, Vila R, Gupta MP, Avella ME, Adzet T, Canigueral S (1998) Antiinflammatory activity of Anthurium cerrocampanense Croat in rats, mice. J Ethnopharm 61:243–248CrossRefGoogle Scholar
  20. Shawali AS (1977) Synthesis and tautomeric structure of some 2H-pyrazolo[3,4-d]pyridazines. J Heterocycl Chem 14:375–381CrossRefGoogle Scholar
  21. Tewari AK, Mishra A (2001) Synthesis and anti-inflammatory activities of N4, N5-isubstituted-3-methyl-1H-pyrazolo[3,4-c]pyridazines. Bioorganic Med Chem 9:715–718CrossRefGoogle Scholar
  22. Tewari AK, Mishra L, Verma HN, Mishra A (2002) Synthesis and antifungal activity of 4-substituted-3,7-dimethyl-pyrazolo[3,4-e][1,2, 4]triazine. Indian J Chem 41B:664–667Google Scholar
  23. Tisler M, Stanounic B (1973) In: Castle RN (ed) The chemistry of heterocyclic compounds. Wiley, New York, p 785Google Scholar
  24. Vogel AL (1978) Text-book of practical organic chemistry, 4th edn. New York: Longman, p 595Google Scholar
  25. Winter CA, Risley EA, Nuss GW (1962) Carrageenin-induced edema in hind paw of the rat as an assay for antiinflammatory drugs. Proc Soc Exp Biol Med 111:544–547PubMedGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  • Ashish Kumar Tewari
    • 1
  • Rashmi Dubey
    • 2
  • Anil Mishra
    • 2
  1. 1.Department of Chemistry, Faculty of ScienceBanaras Hindu UniversityVaranasiIndia
  2. 2.Department of ChemistryLucknow UniversityLucknowIndia

Personalised recommendations