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Synthesis of its Tautomeric Forms and New 6-Substituted Pyridazin-3(2H)-one Analogs  

Kim, Chaewon (College of Pharmacy, Duksung Women's University)
Park, Myung-Sook (College of Pharmacy, Duksung Women's University)
Publication Information
YAKHAK HOEJI / v.57, no.5, 2013 , pp. 316-322 More about this Journal
Abstract
The new pyridazinone analogs were synthesized for development of candidates to retain anticancer activity. Various 6-substituted pyridazin-3(2H)-ones were prepared from the pyridazinyl chloride 3a~d via endothermic nucleophilic substitution with hydroxide ion as nucleophile for 2~48 h. Pyridazinyl chloride 3a~d could be converted to hydroxypyridazines (or pyridazin-3(2H)ones) using 1~5 equivalents of water (or 1 equivalent of sodium hydroxide) at reflux in DMF. The tautomerism of lactim form to lactam form was also accomplished in pyridazine derivatives. Formation of pyridazinones 10 was undertaken with stirring using sodium hydroxide at reflux in DMF for 2 h. Synthetic compounds were identified using NMR spectrum.
Keywords
pyridazinones; hydroxypyridazines; endothermic nucleophilic substitution; tautomeric forms;
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1 Katrusiak, A., Piechowiak, P. and Katrusiak, A. : Synthesis, tautomeric forms specific intermolecular interactions, and its 4,5-dihydro analogs. J. Mol. Struct. 998, 84 (2011).   DOI
2 Salivers, R., Dupas, G., Ple, N., Queguiner, G. and Turck, A. : Solid-phase synthesis of 6-arylpyridazin-3(2H)-ones. J. Comb. Chem. 7, 414 (2005).   DOI
3 Feshin, V. P., Giller, S. A., Avota, L. Y. and Voronkov, M. G. : Study of chloro derivatives of pyridazine and the products of silylation of pyridazine and 6-pyridazone derivatives by $Cl^{35}$ nuclear quadrupole resonanse. Chem. Heterocycl. Compd. 12, 440 (1976).   DOI
4 Rathish, I. G., Javed, K., Ahmad, S., Bano, S., Alam, M. S., Akhter, M., Pillai, K. K., Ovais, S. and Samim, M. : Synthesis and evaluation of anticancer activity of some novel 6-aryl-2-(psulfamylphenyl)- pyridazin-3(2H)-ones. Eur. J. Med. Chem. 49, 304 (2012).   DOI
5 Yaseen, S., Ovais, S., Bashir, R., Rathore, P., Samim, M., Singh, S., Nair, V. and Javed, K. Synthesis and biological evaluation of 4-arylphthalazones bearing benzenesulaonamide as antiinflammatory and anti-cancer agents. Arch. Pharm. Chem. Life Sci. 12, 440 (2013).
6 Hondo, T., Warizaya, M., Niimi, T., Namatame, I., Yamaguchi, T., Nakanishi, K., Hamajima, T., Harada, K., Sakashita, H., Matsumoto, Y., Orita, M. and Takeuchi, M. : 4- Hydroxypyridazin-3(2H)-one derivatives as novel d-amino acid oxidase inhibitors. J. Med. Chem. 56, 3582 (2013).   DOI
7 Malinka, W., Redzicka, A. and Lozach, O. : New derivatives of pyrrolo[3,4-d]pyridazinone and their anticancer effects. IL Farmaco 59, 457 (2004).   DOI
8 Murty, M. S. R., Rao, R., Ram, K. R., Yadav, J. S., Antony, J. and Anto, R. J. : Synthesis and preliminary evaluation activity studies of novel 4-(aryl/heteroaryl-2-ylmethyl)-6-phenyl-2-[3- (4-substitutedpiperazine-1-yl)propyl]pyridazin-3(2H)-one derivatives as anticancer agents. Med. Chem. Res. 21, 3161 (2012).   DOI
9 Al-Tel, T. H. : Design and synthesis of novel tetrahydro-2HPyrano[ 3,2-c]Pyridazin-3(6H)-one derivatives as potential anticancer agents. Eur. J. Med. Chem. 45, 5724 (2010).   DOI
10 Taft, W. E., Adams, J. and Curran, W. V. : 5-Amino-3- chloropyridazine. a clarification. J. Org. Chem. 26, 605 (1961).   DOI
11 Park, E. H. and Park, M. S. : Synthesis of potential anticancer 6-allylthio-3-aminopyridazine derivatives. J. Kor. Chem. Soc. 51, 3, 244 (2007).   DOI
12 Katrusiak, A. and Katrusiak, A. : Tautomeric variety and methylation of 3,6-dihydroxy-4-methylpyridazine. J. Mol. Struct. 694, 85 (2004).   DOI
13 Park, E. H. and Park, M. S. : Oxidation of Pyridazinyl sulfides; Synthesis of new pyridazinyl sulfoxides and pyridazinyl sulfones with aqueous hydrogen peroxide. Yakhak Hoeji 56, 390 (2012).
14 Lee, M. S., Kim, E. S., Moon, A. and Park, M. S. : Synthesis of novel allylthio heterocyclo(or aryl)alkylaminopyridazines and their anticancer activity against SK-Hep-1 cells. Bull. Korean Chem. Soc. 30, 83 (2009).   DOI
15 Won, Y. H. and Park, M. S. : Synthesis and anticancer activities of new 3-allylthio-6-(mono or disubstituted) aminopyridazines. Arch. Pharm. Res. 33, 189 (2010).   DOI