Synthesis of N-Aryl and N-Heteroaryl γ-, δ-, and ε-Lactams Using Deprotometalation–Iodination and N-Arylation, and Properties Thereof

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 two-fold 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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SYNTHESIS, Georg Thieme Verlag, 2017, 49 (19), pp.4500 - 4516. 〈10.1055/s-0036-1590798〉
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Soumis le : mercredi 11 octobre 2017 - 15:42:22
Dernière modification le : jeudi 13 décembre 2018 - 01:27:50

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Florence Mongin, Rim Amara, Ghenia Bentabed-Ababsa, Madani Hedidi, Joseph Khoury, et al.. Synthesis of N-Aryl and N-Heteroaryl γ-, δ-, and ε-Lactams Using Deprotometalation–Iodination and N-Arylation, and Properties Thereof. SYNTHESIS, Georg Thieme Verlag, 2017, 49 (19), pp.4500 - 4516. 〈10.1055/s-0036-1590798〉. 〈hal-01614826〉

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