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This study explores the synthesis of halogenated 1-arylpyrazoles as potential bioactive compounds with promising anti-inflammatory and analgesic properties. The researchers successfully employed 1,3-dipolar cycloaddition techniques involving sydnones and acetylenic dipolarophiles to obtain these pyrazoles efficiently. The resulting compounds, decorated with fluorine and bromine atoms, exhibit structural similarities to existing pharmaceuticals like SC-558. Detailed spectral characterization confirms the success of the synthesis, paving the way for further investigation into their therapeutic potential.
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Halogenated 1-arylpyrazoles as potential bioactive scaffolds Denisa Dumitrescu,1 Marcel Mirel Popa,2 Florea Dumitrascu2 1Faculty of Pharmacy, "Ovidius" University, Constantza, Romania 2Center for Organic Chemistry "C. D. Nenitzescu", Bucharest, Romania Objective The objective of the study was to obtain privileged structures such as pyrazoles which are attractive scaffolds in pharmaceutical chemistry due to their anti-inflammatory and analgesic properties1 among others.2 Introduction Substituted pyrazoles were target for numerous synthetic strategies3 the 1,3-dipolar cycloaddition of sydnones with different dipolarphiles being one of the most elegant.4 Pharmaceutical active compounds with fluorine atoms in their structure were of interest due to the influence of fluorine atom on their bioavailability.5 Results and Discussion Herein we present the simple and efficient synthesis of halogen decorated pyrazoles with the fluorine and/or bromine atoms attached to the 1-aryl moiety by 1,3-dipolar cycloaddition of the corresponding sydnones to acetylenic dipolarophiles. The new 1-arylpyrazoles were obtained in good yields and characterized by spectroscopical methods. Conclusions Such compounds are structurally analogous to the 1-phenylpyrazole drugs or lead compounds (i.e SC-558) and thus could be of interest for the study of their anti-inflammatory or analgesic properties. • References: • Ragabet et al. Eur. J. Med. Chem.2013, 63, 645 • Song et al. Eur. J. Med. Chem.2013, 60, 376 • Fustero et al. Chem. Rev.2011, 111, 6984 • Dumitrascu et al. Arkivoc2002, (ii), 80 • Bohm et al. ChemBioChem2004, 5, 637-643
