Exploration on structure and anticonvulsant activity of transition metal complexes derived from an “end-off” compartmental bis-quinoxaline derivative with phthalazinyl-diazine as endogenous bridge

  • Srinivasa Budagumpi
  • Naveen V. Kulkarni
  • M. P. Sathisha
  • Sandeep P. Netalkar
  • Vidyanand K. Revankar
  • D. K. Suresh
Original Paper

Abstract

An oligoquinoxaline derivative with phthalazine core has been prepared by condensation of 1,4-dihydrazinophthalazine with 2,3-dichloroquinoxaline in dry ethanol followed by acid hydrolysis. Classical endogenous bridging of phthalazine core with its diazine fragment was established in the transition metal(II) complexes derived from the ligand system by using various physicochemical and spectral techniques. The organic host acts as a hexadentate chelate with N4O2 donating sites for coordination towards later first-row transition metal ions. Complexes are in good agreement with the octahedral geometry and found to be 1:1 electrolytes. All synthesized compounds were screened for anticonvulsant activity in Wistar rats by using maximal electroshock method. The ligand, and Co(II) and Ni(II) complexes show appreciable suppression towards electroshock-induced seizures.

Graphical Abstract

Keywords

Quinoxaline Phthalazine Anticonvulsant Octahedral Maximal electroshock Seizures 

References

  1. 1.
    Sarro GD, Gitto R, Russo E, Ibbadu GF, Barreca ML, Luca LD, Chimirri A (2005) Curr Top Med Chem 5:31CrossRefGoogle Scholar
  2. 2.
    Chimirri A, Sarro GD, Quartarone S, Barreca ML, Caruso R, Luca LD, Gitto R (2004) Pure Appl Chem 76:931CrossRefGoogle Scholar
  3. 3.
    Grasso S, Sarro GD, Sarro AD, Micale N, Zappala M, Puja G, Baraldi M, Micheli CD (2000) J Med Chem 43:2851CrossRefGoogle Scholar
  4. 4.
    Gitto R, Orlando V, Quartarone S, Sarro GD, Sarro AD, Russo E, Ferreri G, Chimirri A (2003) J Med Chem 46:3758CrossRefGoogle Scholar
  5. 5.
    Pelletier JC, Hesson DP, Jones KA, Costa AM (1996) J Med Chem 39:343CrossRefGoogle Scholar
  6. 6.
    Larsen PK, Ebert B, Lund TM, Osborne HB, Slok KA, Johansen TN, Brehn L, Madsen U (1996) Eur J Med Chem 31:515CrossRefGoogle Scholar
  7. 7.
    Klingelea J, Decherta S, Meyer F (2009) Coord Chem Rev 253:2698CrossRefGoogle Scholar
  8. 8.
    Schneider CJ, Cashion JD, Moubaraki B, Neville SM, Batten SR, Turner DR, Murray KS (2007) Polyhedron 26:1764CrossRefGoogle Scholar
  9. 9.
    Chandrasekhar V, Thirumoorthi R, Azhakar R (2007) Organometallics 26:26CrossRefGoogle Scholar
  10. 10.
    Eisenwiener A, Neuburger M, Kaden TA (2007) Dalton Trans 218Google Scholar
  11. 11.
    Dey SK, Abedin TSM, Dawe LN, Tandon SS, Collins JL, Thompson LK, Postnikov AV, Alam MS, Müller P (2007) Inorg Chem 46:7767CrossRefGoogle Scholar
  12. 12.
    Annigeri SM, Sathisha MP, Revankar VK (2007) Transition Met Chem 32:81CrossRefGoogle Scholar
  13. 13.
    Budagumpi S, Kulkarni NV, Kurdekar GS, Sathisha MP, Revankar VK (2010) Eur J Med Chem 45:455CrossRefGoogle Scholar
  14. 14.
    Kuzelka J, Mukhopadhyay S, Spingler B, Lippard SJ (2004) Inorg Chem 43:1751CrossRefGoogle Scholar
  15. 15.
    Saha NC, Saha A, Butcher RJ, Chaudhuri S, Saha N (2002) Inorg Chim Acta 339:348CrossRefGoogle Scholar
  16. 16.
    Budagumpi S, Sathisha MP, Kulkarni NV, Kurdekar GS, Revankar VK (2010) J Incl Phenom Macrocycl Chem 66:327CrossRefGoogle Scholar
  17. 17.
    Budagumpi S, Kurdekar GS, Kulkarni NV, Revankar VK (2009) J Incl Phenom Macrocycl Chem. doi:101007/s10847-009-9701-z
  18. 18.
    Lever ABP (1968) Inorganic Electronic Spectroscopy. Elsevier, AmsterdamGoogle Scholar
  19. 19.
    Sathisha MP, Shetti UN, Revankar VK, Pai KSR (2008) Eur J Med Chem 43:2338CrossRefGoogle Scholar
  20. 20.
    Geary WJ (1971) Coord Chem Rev 7:81CrossRefGoogle Scholar
  21. 21.
    Clarke EGC, Clarke ML (1977) Veterinary Toxicology. Cassed and Collier, LondonGoogle Scholar
  22. 22.
    Cucino RF, Pandey RK (2005) J Org Chem 70:5344CrossRefGoogle Scholar
  23. 23.
    Reynolds GA, Van Allen JA, Tinker JF (1959) J Org Chem 24:1205CrossRefGoogle Scholar
  24. 24.
    Mishra AK, Dandiya PC, Kulkarni SK (1973) Indian J Pharmacol 5:449Google Scholar
  25. 25.
    Kulkarni SK (1981) Arch Int Pharmacodyn 252:124Google Scholar

Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • Srinivasa Budagumpi
    • 1
    • 2
  • Naveen V. Kulkarni
    • 3
  • M. P. Sathisha
    • 1
  • Sandeep P. Netalkar
    • 1
  • Vidyanand K. Revankar
    • 1
  • D. K. Suresh
    • 4
  1. 1.Department of ChemistryKarnatak University, Pavate NagarDharwadIndia
  2. 2.Department of Chemical EngineeringPusan National UniversityPusanRepublic of Korea
  3. 3.Department of ChemistryTechnion - Israel Institute of TechnologyHaifaIsrael
  4. 4.Department of PharmacologyLuqman College of PharmacyGulbargaIndia

Personalised recommendations