Halogenated 1-arylpyrazoles as potential bioactive scaffolds. Denisa Dumitrescu, 1 Marcel Mirel Popa, 2 Florea Dumitrascu 2 1 Faculty of Pharmacy, "Ovidius" University, Constantza, Romania 2 Center for Organic Chemistry "C. D. Nenitzescu", Bucharest, Romania. Objective.
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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
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
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.
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.