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Optimization and SAR for dual ErbB-1/ErbB-2 tyrosine kinase inhibition in the 6-furanylquinazoline series.

Publication ,  Journal Article
Petrov, KG; Zhang, Y-M; Carter, M; Cockerill, GS; Dickerson, S; Gauthier, CA; Guo, Y; Mook, RA; Rusnak, DW; Walker, AL; Wood, ER; Lackey, KE
Published in: Bioorg Med Chem Lett
September 1, 2006

Synthetic modifications on a 6-furanylquinazoline scaffold to optimize the dual ErbB-1/ErbB-2 tyrosine kinase inhibition afforded consistent SAR whereby a 4-(3-fluorobenzyloxy)-3-haloanilino provided the best enzyme potency and cellular selectivity. Changes made to the 6-furanyl group had little impact on the enzyme activity, but appeared to dramatically affect the cellular efficacy. The discovery of lapatinib emerged from this work.

Duke Scholars

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Published In

Bioorg Med Chem Lett

DOI

ISSN

0960-894X

Publication Date

September 1, 2006

Volume

16

Issue

17

Start / End Page

4686 / 4691

Location

England

Related Subject Headings

  • Structure-Activity Relationship
  • Receptor, erbB-2
  • Receptor, ErbB-2
  • Quinazolines
  • Protein Kinase Inhibitors
  • Molecular Structure
  • Models, Molecular
  • Medicinal & Biomolecular Chemistry
  • Lapatinib
  • Inhibitory Concentration 50
 

Citation

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Petrov, K. G., Zhang, Y.-M., Carter, M., Cockerill, G. S., Dickerson, S., Gauthier, C. A., … Lackey, K. E. (2006). Optimization and SAR for dual ErbB-1/ErbB-2 tyrosine kinase inhibition in the 6-furanylquinazoline series. Bioorg Med Chem Lett, 16(17), 4686–4691. https://doi.org/10.1016/j.bmcl.2006.05.090
Petrov, Kimberly G., Yue-Mei Zhang, Malcolm Carter, G Stuart Cockerill, Scott Dickerson, Cassandra A. Gauthier, Yu Guo, et al. “Optimization and SAR for dual ErbB-1/ErbB-2 tyrosine kinase inhibition in the 6-furanylquinazoline series.Bioorg Med Chem Lett 16, no. 17 (September 1, 2006): 4686–91. https://doi.org/10.1016/j.bmcl.2006.05.090.
Petrov KG, Zhang Y-M, Carter M, Cockerill GS, Dickerson S, Gauthier CA, et al. Optimization and SAR for dual ErbB-1/ErbB-2 tyrosine kinase inhibition in the 6-furanylquinazoline series. Bioorg Med Chem Lett. 2006 Sep 1;16(17):4686–91.
Petrov, Kimberly G., et al. “Optimization and SAR for dual ErbB-1/ErbB-2 tyrosine kinase inhibition in the 6-furanylquinazoline series.Bioorg Med Chem Lett, vol. 16, no. 17, Sept. 2006, pp. 4686–91. Pubmed, doi:10.1016/j.bmcl.2006.05.090.
Petrov KG, Zhang Y-M, Carter M, Cockerill GS, Dickerson S, Gauthier CA, Guo Y, Mook RA, Rusnak DW, Walker AL, Wood ER, Lackey KE. Optimization and SAR for dual ErbB-1/ErbB-2 tyrosine kinase inhibition in the 6-furanylquinazoline series. Bioorg Med Chem Lett. 2006 Sep 1;16(17):4686–4691.
Journal cover image

Published In

Bioorg Med Chem Lett

DOI

ISSN

0960-894X

Publication Date

September 1, 2006

Volume

16

Issue

17

Start / End Page

4686 / 4691

Location

England

Related Subject Headings

  • Structure-Activity Relationship
  • Receptor, erbB-2
  • Receptor, ErbB-2
  • Quinazolines
  • Protein Kinase Inhibitors
  • Molecular Structure
  • Models, Molecular
  • Medicinal & Biomolecular Chemistry
  • Lapatinib
  • Inhibitory Concentration 50