Elaboration of tetra-orthogonally-substituted aromatic scaffolds towards novel EGFR-kinase inhibitors

Close, Adam J, Jones, Rhiannon N, Ocasio, Cory A, Kemmitt, Paul, Roe, S Mark and Spencer, John (2016) Elaboration of tetra-orthogonally-substituted aromatic scaffolds towards novel EGFR-kinase inhibitors. Organic and Biomolecular Chemistry, 14. pp. 8246-8252. ISSN 1477-0520

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Abstract

Nitration of three regioisomers of bromo-fluorobenzaldehyde proceeds regioselectively, notably with H2SO4/HNO3 at 0 °C. The thereby synthesized tetrasubstituted aromatics, endowed with orthogonal substituents, can be elaborated via Pd-catalysed coupling, reduction and reductive amination reactions. As a test-case, these compounds were converted into EGFR inhibitors related to Gefitinib, whose activity was rationalised by docking studies.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry
Q Science > QD Chemistry > QD0241 Organic chemistry
Depositing User: John Spencer
Date Deposited: 26 Jul 2016 08:30
Last Modified: 07 Mar 2017 07:55
URI: http://sro.sussex.ac.uk/id/eprint/62101

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Astra Zeneca regioselective transition metal mediated routesG0878AZUnset