Pyridazin-3(2 H )-ones: the versatile pharmacophore of medicinal significance
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Med Chem Res DOI 10.1007/s00044-012-0261-1
REVIEW ARTICLE
Pyridazin-3(2H)-ones: the versatile pharmacophore of medicinal significance Ranju Bansal • Sridhar Thota
Received: 7 March 2012 / Accepted: 22 September 2012 Ó Springer Science+Business Media New York 2012
Abstract Pyridazin-3(2H)-one derivatives have attracted the attention of medicinal chemists during the last decade due to their diverse pharmacological activities. Easy functionalization of various ring positions of pyridazinones makes them an attractive synthetic building block for designing and synthesis of new drugs. The incorporation of this versatile biologically accepted pharmacophore in established medicinally active molecules results in wide range of pharmacological effects. Pyridazinones constitute an interesting group of compounds, many of which possess wide spread pharmacological properties such as antihypertensive, platelet aggregation inhibitory, cardiotonic activities and some are also well known for their pronounced analgesic, anti-inflammatory, antinociceptive, and antiulcer activities. Recently pyridazinones have also been reported as antidiabetic, anticonvulsant, antiasthmatic, and antimicrobial agents. These encouraging reports suggest that this privileged skeleton should be extensively studied for the therapeutic benefits. In view of this, a detailed and updated account of the pharmacological properties of pyridazinones is described in this review. The wide range of synthesized pyridazinone analogs along with their medicinal significance is also presented.
Introduction
Keywords Pyridazin-3(2H)-one Pharmacological activity Anti-inflammatory Cardiovascular effects
Diverse pharmacological properties
R. Bansal (&) S. Thota University Institute of Pharmaceutical Sciences, Panjab University, Sector-14, Chandigarh 160014, India e-mail: [email protected]
Among pyridazine derivatives, 3(2H)-pyridazinones form an important class of compounds mainly due to their diverse pharmacological activities. This privileged structure attracts the interest of medicinal chemists as a nucleus of potential therapeutic utility. The easy functionalization at various ring positions makes them an attractive synthetic building block for designing and synthesis of new drugs. The pyridazin-3(2H)-one skeleton was first prepared by E. Fischer by cyclizing the phenylhydrazone of levulinic acid followed by oxidation in the presence of PCl5. The most common synthesis consists of the reaction of hydrazine or aryl hydrazines either with mixtures of ketones and esters, or with 1,4-dicarbonyl compounds (Lee et al., 2004; Matyus, 1998). Chemical and biological aspects of 4,5disubstituted 3(2H)-pyridazinones derivatives have been detailed in a number of comprehensive reviews (Coates, 1996; Matyus and Czako, 1993; Dal Piaz et al., 1994; Heinisch and Frank, 1990, 1992). In this review the varied pharmacological properties and related medicinal significance of various pyridazinone derivatives is presented.
Pyridazinones show a diverse range of agrochemical and
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