Design, synthesis and molecular modelling studies of novel 3-acetamido-4-methyl benzoic acid derivatives as inhibitors of protein tyrosine phosphatase 1B

Rakse, Monika, Karthikeyan, Chandrabose, Deora, Girdhar Singh, Moorthy, N. S. H. N., Rathore, Vandana, Rawat, Arun K., Srivastava, A. K. and Trivedi, Piyush (2013) Design, synthesis and molecular modelling studies of novel 3-acetamido-4-methyl benzoic acid derivatives as inhibitors of protein tyrosine phosphatase 1B. European Journal of Medicinal Chemistry, 70 469-476. doi:10.1016/j.ejmech.2013.10.030


Author Rakse, Monika
Karthikeyan, Chandrabose
Deora, Girdhar Singh
Moorthy, N. S. H. N.
Rathore, Vandana
Rawat, Arun K.
Srivastava, A. K.
Trivedi, Piyush
Title Design, synthesis and molecular modelling studies of novel 3-acetamido-4-methyl benzoic acid derivatives as inhibitors of protein tyrosine phosphatase 1B
Journal name European Journal of Medicinal Chemistry   Check publisher's open access policy
ISSN 0223-5234
1768-3254
Publication date 2013-01-01
Sub-type Article (original research)
DOI 10.1016/j.ejmech.2013.10.030
Volume 70
Start page 469
End page 476
Total pages 8
Place of publication Issy les Moulineaux, Cedex, France
Publisher Elsevier Masson
Language eng
Subject 3002 Drug Discovery
3004 Pharmacology
Abstract A novel series of 3-acetamido-4-methyl benzoic acid derivatives designed on the basis of vHTS hit ZINC02765569 were synthesized and screened for PTP1B inhibitory activity. The most potent compounds 3-(1-(5-methoxy-1H-benzo[d] imidazol-2-ylthio)acetamido)-4-methyl benzoic acid (10c, IC50 8.2 μM) and 3-(2-(benzo[d]thiazol-2-ylthio)acetamido)-4-methyl benzoic acid (10e, IC50 8.3 μM) showed maximum PTP1B inhibitory activity. Docking studies were also performed to understand the nature of interactions governing the binding mode of the designed molecules within the active site of the PTP1B enzyme.
Keyword Acetamido benzoic acid derivatives
Diabetes
Lead optimization
Molecular modelling
PTP1B
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2014 Collection
School of Pharmacy Publications
 
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