Design and synthesis of 2-substituted benzoxazoles as novel PTP1B inhibitors

A series of benzoxazole compounds containing oxamic acid were synthesized and screened for the PTP1B inhibition. Compound 31d showed best biochemical potency (Ki) of 6.7μM. Structure–activity relationship were explained with the help of molecular modeling approach.

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2013-05, Vol.23 (9), p.2579-2584
Main Authors: Chandrasekharappa, Arun P., Badiger, Sangamesh E., Dubey, Pramod K., Panigrahi, Sunil K., Manukonda, Sekhar Reddy V.V.V.
Format: Article
Language:English
Subjects:
Animals
Benzimidazole
Benzoxazole
Benzoxazoles - chemical synthesis
Benzoxazoles - chemistry
Benzoxazoles - metabolism
Binding Sites
Diabetes
Drug Design
Enzyme Inhibitors - chemical synthesis
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - metabolism
Mice
Molecular Docking Simulation
Oxamic Acid - chemistry
Oxamic acids
Protein Binding
Protein Structure, Tertiary
Protein Tyrosine Phosphatase, Non-Receptor Type 1 - antagonists & inhibitors
Protein Tyrosine Phosphatase, Non-Receptor Type 1 - metabolism
PTP1B
pTyr mimetics
Structure-Activity Relationship
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Description
Summary:A series of benzoxazole compounds containing oxamic acid were synthesized and screened for the PTP1B inhibition. Compound 31d showed best biochemical potency (Ki) of 6.7μM. Structure–activity relationship were explained with the help of molecular modeling approach.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2013.02.109