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

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posted on 2023-06-09, 02:14 authored by Adam J Close, Rhiannon N Jones, Cory A Ocasio, Paul Kemmitt, S Mark Roe, John SpencerJohn Spencer
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.

Funding

Astra Zeneca regioselective transition metal mediated routes; G0878; AZ

History

Publication status

  • Published

File Version

  • Published version

Journal

Organic and Biomolecular Chemistry

ISSN

1477-0520

Publisher

Royal Society of Chemistry

Volume

14

Page range

8246-8252

Department affiliated with

  • Chemistry Publications

Full text available

  • Yes

Peer reviewed?

  • Yes

Legacy Posted Date

2016-07-26

First Open Access (FOA) Date

2016-07-26

First Compliant Deposit (FCD) Date

2016-07-25

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