31224-43-8Relevant articles and documents
Understanding Cu(ii)-based systems for C(sp3)-H bond functionalization: insights into the synthesis of aza-heterocycles
Camats, Marc,Gómez, Montserrat,Mallet-Ladeira, Sonia,Pla, Daniel,favier, Isabelle
supporting information, p. 219 - 227 (2021/12/29)
Herein we report the synthesis of imidazo[1,5-a]pyridine heterocyclesviaa Cu(ii)-mediated functionalization of α′-C(sp3)-H bonds of pyridinylaldimines and subsequent cyclization. This strategy exploits the inherent directing ability of heteroleptic aldimine and pyridine groups in the substrate yielding the C-H functionalization of α′-methylene groups in a regioselective fashion over distant methyl or methylene groups in β or γ positions. The observed correlation between the nature of the anionic ligands (halidevs.carboxylate) bonded to copper and the chemoselectivity of the C(sp3)-H activation process points to a concerted metalation-deprotonation pathway prior to cyclization to furnish the corresponding imidazo[1,5-a]pyridine derivative. This copper-mediated C(sp3)-H bond functionalization reaction works for a variety of substrates incorporating linear alkyl chains (from 3 to 12 carbon atoms), and good functional group tolerance (aryl, ether and ester groups). Cu-Catalyzed C(sp2)-H cyanation on the imidazole ring can then take place selectively under oxidative conditions.
TRPM8 ANTAGONISTS AND THEIR USE IN TREATMENTS
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Page/Page column 89-90, (2013/02/28)
Compounds of Formula (I) are useful as antagonists of TRPM8. Such compounds are useful in treating a number of TRPM8 mediated disorders and conditions and may be used to prepare medicaments and pharmaceutical compositions useful for treating such disorders and conditions. Examples of such disorders include, but are not limited to, migraines and neuropathic pain. Compounds of Formula (I) have the above structure, where the definitions of the variables are provided herein.
Optimisation of ITK inhibitors through successive iterative design cycles
Herdemann, Matthias,Weber, Alexander,Jonveaux, Jér?me,Schwoebel, Frank,Stoeck, Michael,Heit, Isabelle
supporting information; body text, p. 1852 - 1856 (2011/05/05)
Based on a hit cluster of compounds inhibiting interleukin-2 inducible T-cell kinase (ITK) in the submicromolar range a series of ITK inhibitor libraries were synthesized. Through iterative design cycles including kinase crystal structure information, indolylindazole libraries were identified which showed low nanomolar activity in enzymatic and cellular assays. The potential of these novel lead series was confirmed through in vivo tests in an anti-CD3-IL2 mouse model. The intravenous administration of highly potent ITK inhibitor 11o resulted in dose-dependent, efficient suppression of IL-2.
