RSS-Feed abonnieren
DOI: 10.1055/s-0031-1300592
Synthesis, characterization and cytotoxic activity of new salicylaldehyde benzoylhydrazone derivatives as potential anti-proliferative agents
Publikationsverlauf
Publikationsdatum:
09. Februar 2012 (online)
![](https://www.thieme-connect.de/media/amf/201112/lookinside/thumbnails/10.1055-s-0031-1300592-1.jpg)
Abstract
Three new hydrazones, derivatives of salicylaldehyde benzoylhydrazone, were synthesized as potential anti-proliferative compounds. The structure of the new compounds was characterized by elemental and thermo-gravimetric analyses, IR, 1H and 13C-NMR spectroscopy and quantum chemical calculations. The cytotoxic effects of new hydrazones were examined on a wide spectrum of human tumor cell lines. The obtained results revealed that all compounds proved to be equipotent or more active than cisplatin, and far more active than another utilized anticancer drug, melphalan. On the basis of IC50 values the compound 3-methoxy-salicylaldehyde isonicotinoylhydrazone (mSIH) was found to be the most active cytotoxic agent at all cell lines.
-
References
- 1 Sondhi SM, Dinodia M, Kumar A. Synthesis, anti-inflammatory and analgesic activity evaluation of some amidine and hydrazone derivatives. Bioorg Med Chem. 2006; 14: 4657-63
- 2 Cunha AC, Tributino JLM, Miranda ALP, Fraga CAM, Bar-reiro EJ. Synthesis and pharmacological evaluation of novel antinociceptive N-substituted-phenylimidazolyl-4-acylhy-drazone derivatives. Il Farmaco. 2002; 57: 999-1007
- 3 Sridhar SK, Ramesh A. Synthesis and pharmacological activities of hydrazones, Schiff and Mannich bases of isatin derivatives. Biol Pharm Bull. 2001; 24: 1149-52
- 4 Savini L, Massarelli P, Travagli V, Pellerano C, Novellino E, Cosentino S et al. New a-(N)-heterocyclichydrazones: evaluation of anticancer, anti-HIV and antimicrobial activity. Eur J Med Chem. 2004; 39: 113-22
- 5 Ponka P, Borova J, Neuwirt J, Fuchs O. Mobilization of iron from reticulocytes. FEBS Lett. 1979; 97: 317-21
- 6 Richardson D R, Bernhardt P V. Crystal and molecular structure of 2-hydroxy-l-naphthaldehyde isonicotinoyl hydrazone (NIH) and its iron (III) complex: an iron chelator with anti-tumor activity. J Biol Inorg Chem. 1999; 4: 266-73
- 7 Johnson DK, Murphy TB, Rose NJ, Goodwin WH, Pickart L. Cytotoxic chelators and chelates 1. Inhibition of DNA synthesis in cultured rodent and human cells by aroylhy-drazones and by a copper (II) complex of salicylaldehyde benzoyl hydrazone. Inorg Chim Acta. 1982; 67: 159-65
- 8 Pickart L, Goodwin WH, Murphy TB, Johnson DK. Growth-inhibitory analog of the GLY-HIS-LYS-Cu(II) complex. J Cell Biochem. 1982; (6 Suppl) L482
- 9 Pickart L, Goodwin WH, Burgua W, Murphy TB, Johnson DK. Inhibition of the growth of cultured cells and an implanted fibrosarcoma by aroylhydrazone analogs of the Gly-His-Lys-Cu(II) complex. Biochem Pharmacol. 1983; 32: 3868-71
- 10 Becke AD, Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys. 1993; 98: 5648-52
- 11 Lee C, Yang W, Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev. B 1988; 37 (2) 785-9
- 12 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods. 1983; Dec; 16 65 (l–2) 55-63
- 13 Konstantinov SM, Eibl H, Berger MR. BCR-ABL influences the antileukaemic efficacy of alkylphosphocholines. Br J Haematol. 1999; Nov; 107 (2) 365-80
- 14 Edward JT, Gauthier M, Chubb FL, Ponka P. Synthesis of new acylhydrazones as iron-chelating compounds. J Chem Eng Data. 1988; 33: 538-40
- 15 Lyubchova A, Cossé-Barbi A, Doucet JP, Robert F, Souron JP, Quarton M. Salicylaldehyde benzoyl hydrazone. Acta Cryst. 1995; C51: 1893-5