From 2000 to mid-2010: a fruitful decade for the synthesis of pyrazoles.
About: This article is published in Chemical Reviews.The article was published on 2011-08-01. It has received 839 citations till now.
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TL;DR: The different synthesis methods and the pharmacological properties of pyrazole derivatives developed by many scientists around the globe are highlighted.
Abstract: Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. The presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antipsychotic CDPPB, the anti-obesity drug rimonabant, difenamizole, an analgesic, betazole, a H2-receptor agonist and the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Owing to this diversity in the biological field, this nucleus has attracted the attention of many researchers to study its skeleton chemically and biologically. This review highlights the different synthesis methods and the pharmacological properties of pyrazole derivatives. Studies on the synthesis and biological activity of pyrazole derivatives developed by many scientists around the globe are reported.
520 citations
Cites background or methods from "From 2000 to mid-2010: a fruitful d..."
...Two series of new pyrazoles, namely pyrazolo[1,5-a][1,3,5]triazine-2,4-dione and pyrazolo-[1,5-c][1,3,5]thiadiazine-2-one derivatives, were synthesized as potential inhibitors of the photosynthetic electron transport chain at the photosystem II level....
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...Pyrazolo[5,1-f] [1,6]naphthyridine 491 showed the highest affinity for PDE10A enzyme (IC50 = 40 nM) [385]....
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...Several [1,2,4]triazolo[1,5-a]pyridine-bearing pyrazole...
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...3-(2-chloroethyl)-5-methyl-6-phenyl-8- (trifluoromethyl)-5,6-[3,4-f][1,2,3,5]tetrazepin-4-(3H)-one 277 synthesized by Maggio et al....
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...A new 2-aroyl-[1]benzopyrano[4,3-c]pyrazol-4(1H)-one derivatives containing hydrazide-hydrazone analogues were prepared and tested in vitro for their anti-mycobacterial activity against reference strain M....
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366 citations
274 citations
TL;DR: Progress is made in the catalytic asymmetric synthesis of pyrazoles and pyrazolones using pyrazolin-5-one derivatives using organo- and metal-catalysts.
215 citations
TL;DR: In this article, a survey on transition metal containing coordination polymers and metal-organic frameworks (MOFs) with poly(pyrazole)-and poly (pyrazolate)-based ligands is presented, where up to three N-donor heterocyclic rings are organized on rigid or flexible cores.
201 citations
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3,685 citations
TL;DR: In this article, the authors highlight the recent developments in the copper-mediated (both stoichiometric and catalytic) reactions of aryl boronic acids as reaction partners in both O- and N-arylation.
Abstract: The copper-mediated C(aryl)N, C(aryl)O, and C(aryl)S bond formation is an important transformation and has been developed to include a wide range of substrates. This Review highlights the recent developments in the copper-mediated (both stoichiometric and catalytic) reactions of aryl boronic acids, aryl halides, iodonium salts, siloxanes, stannanes, plumbanes, bismuthates, and trifluoroborate salts as aryl donors. In particular, the recent introduction of boronic acids as reaction partners in both O- and N-arylation has been a significant discovery and will occupy centre-stage in this review. Clear improvements can be obtained by the correct choice of copper source, base, ligands, and other additives. Mechanistic investigations should provide insight into the catalytically active species, which would aid in the development of milder, more-efficient methods.
2,280 citations
TL;DR: 1i (4-[5-(4-methylphenyl)-3-(trifluoromethyl)- H-pyrazol-1-yl]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis, is identified.
Abstract: A series of sulfonamide-containing 1,5-diarylpyrazole derivatives were prepared and evaluated for their ability to block cyclooxygenase-2 (COX-2) in vitro and in vivo. Extensive structure-activity relationship (SAR) work was carried out within this series, and a number of potent and selective inhibitors of COX-2 were identified. Since an early structural lead (1f, SC-236) exhibited an unacceptably long plasma half-life, a number of pyrazole analogs containing potential metabolic sites were evaluated further in vivo in an effort to identify compounds with acceptable pharmacokinetic profiles. This work led to the identification of 1i (4-[5-(4-methylphenyl)-3-(trifluoromethyl)- H-pyrazol-1-yl]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis.
1,895 citations
TL;DR: Using R-Hydroxy Stannanes as a Model for a Methylenation Reaction and Conclusions and Future Prospects are presented.
Abstract: 6.4. Polyynes 3123 6.5. Using R-Hydroxy Stannanes 3124 6.6. Using the Hurtley Reaction 3124 6.7. Using a Methylenation Reaction 3125 7. Conclusions and Future Prospects 3125 8. Uncommon Abbreviations 3125 9. Acknowledgments 3125 10. Note Added in Proof 3125 11. References 3126 * Authorstowhomcorrespondenceshouldbeaddressed(evano@chimie.uvsq.fr, nicolas.blanchard@uha.fr). † Université de Versailles Saint Quentin en Yvelines. ‡ Université de Haute-Alsace. Chem. Rev. 2008, 108, 3054–3131 3054
1,789 citations
05 Apr 2002
TL;DR: In this paper, the authors present a list of the most important properties of Nitrones and Azomethine Ylides: Nitrones (Jason N. Martin and Raymond C. Jones), Nitronates (Scott E. Denmark and Jeromy J. Cottell), Azides (Chin-Kang Sha and A. K. Mohanakrishnan). Mesoionic Ring Systems (Gordon W. Gribble). Effect of External Reagents (Shuji Kanemasa). Asymmetric Reactions (Kurt Vesterager Gothe
Abstract: Nitrones (Jason N. Martin and Raymond C. F. Jones). Nitronates (Scott E. Denmark and Jeromy J. Cottell). Azomethine Ylides (L. M. Harwood and R. J. Vickers). Carbonyl Ylides (Mark C. McMills and Dennis Wright). Thiocarbonyl Ylides (Grzegorz Mloston and Heinz Heimgartner). Nitrile Oxides (Volker Jager and Pedro A. Colinas). Nitrile Ylides and Nitrile Imines (John T. Sharp). Diazoalkanes (Gerhard Maas). Azides (Chin-Kang Sha and A. K. Mohanakrishnan). Mesoionic Ring Systems (Gordon W. Gribble). Effect of External Reagents (Shuji Kanemasa). Asymmetric Reactions (Kurt Vesterager Gothelf and Karl Anker Jorgensen). Index.
1,041 citations