Skip to Main content Skip to Navigation
Journal articles

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.
Document type :
Journal articles
Complete list of metadatas

Cited literature [7 references]  Display  Hide  Download

https://hal-univ-rennes1.archives-ouvertes.fr/hal-01624382
Contributor : Laurent Jonchère <>
Submitted on : Thursday, October 26, 2017 - 11:40:48 AM
Last modification on : Friday, October 16, 2020 - 3:41:10 AM
Long-term archiving on: : Saturday, January 27, 2018 - 1:05:36 PM

File

Mongin et al. - Fused systems ...
Files produced by the author(s)

Identifiers

Citation

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⟩

Share

Metrics

Record views

387

Files downloads

178