Fused Systems Based on 2-Aminopyrimidines: Synthesis Combining Deprotolithiation-in situ Zincation with N -Arylation Reactions and Biological Properties

Abstract : Various aromatic ketones were first functionalized next to the carbonyl function by deprotolithiation in the presence of a zinc salt followed by iodolysis. The outcome of the reactions was analyzed, and in particular their regioselectivity in the light of the calculated pKa values. The various halogenated ketones were next involved in copper-catalyzed twofold C-N bond formation in order to obtain fused systems based on 2-aminopyrimidines. Besides potential antibacterial effect, reached 2-aminobenzothiopyrano[4,3,2-de]quinazoline proved to inhibit PIM1 (IC50: 0.61 μM) and CDK2/cyclin A (IC50: 2.0 μM) kinases.
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European Journal of Organic Chemistry, Wiley-VCH Verlag, 2017, 2017 (39), pp.5903-5915. 〈10.1002/ejoc.201701004〉
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Madani Hedidi, Julien Maillard, William Erb, Frédéric Lassagne, Yury Halauko, et al.. Fused Systems Based on 2-Aminopyrimidines: Synthesis Combining Deprotolithiation-in situ Zincation with N -Arylation Reactions and Biological Properties. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2017, 2017 (39), pp.5903-5915. 〈10.1002/ejoc.201701004〉. 〈hal-01624382〉

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