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

Monika Rakse; Chandrabose Karthikeyan; Girdhar Singh Deora; N S H N Moorthy; Vandana Rathore; Arun K. Rawat; A. K. Srivastava; Piyush Trivedi

doi:10.1016/j.ejmech.2013.10.030

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

Monika Rakse, Chandrabose Karthikeyan, Girdhar Singh Deora, N S H N Moorthy, Vandana Rathore, Arun K. Rawat, A. K. Srivastava, Piyush Trivedi

Research output: Contribution to journal › Article › Research › peer-review

29 Citations (Scopus)

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.

Original language	English
Pages (from-to)	469-476
Number of pages	8
Journal	European Journal of Medicinal Chemistry
Volume	70
DOIs	https://doi.org/10.1016/j.ejmech.2013.10.030
Publication status	Published - 2013
Externally published	Yes

Keywords

Acetamido benzoic acid derivatives
Diabetes
Lead optimization
Molecular modelling
PTP1B

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.ejmech.2013.10.030

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Rakse, M., Karthikeyan, C., Deora, G. S., Moorthy, N. S. H. N., Rathore, V., Rawat, A. K., Srivastava, A. K., & Trivedi, P. (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. https://doi.org/10.1016/j.ejmech.2013.10.030

@article{3aeca907680f42ac882b38288b668ff4,

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

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. ",

keywords = "Acetamido benzoic acid derivatives, Diabetes, Lead optimization, Molecular modelling, PTP1B",

author = "Monika Rakse and Chandrabose Karthikeyan and Deora, {Girdhar Singh} and Moorthy, {N S H N} and Vandana Rathore and Rawat, {Arun K.} and Srivastava, {A. K.} and Piyush Trivedi",

year = "2013",

doi = "10.1016/j.ejmech.2013.10.030",

language = "English",

volume = "70",

pages = "469--476",

journal = "European Journal of Medicinal Chemistry",

issn = "0223-5234",

publisher = "Elsevier",

}

Rakse, M, Karthikeyan, C, Deora, GS, Moorthy, NSHN, Rathore, V, Rawat, AK, Srivastava, AK & Trivedi, P 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, vol. 70, pp. 469-476. https://doi.org/10.1016/j.ejmech.2013.10.030

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 et al.
In: European Journal of Medicinal Chemistry, Vol. 70, 2013, p. 469-476.

Research output: Contribution to journal › Article › Research › peer-review

TY - JOUR

T1 - Design, synthesis and molecular modelling studies of novel 3-acetamido-4-methyl benzoic acid derivatives as inhibitors of protein tyrosine phosphatase 1B

AU - Rakse, Monika

AU - Karthikeyan, Chandrabose

AU - Deora, Girdhar Singh

AU - Moorthy, N S H N

AU - Rathore, Vandana

AU - Rawat, Arun K.

AU - Srivastava, A. K.

AU - Trivedi, Piyush

PY - 2013

Y1 - 2013

N2 - 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.

AB - 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.

KW - Acetamido benzoic acid derivatives

KW - Diabetes

KW - Lead optimization

KW - Molecular modelling

KW - PTP1B

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U2 - 10.1016/j.ejmech.2013.10.030

DO - 10.1016/j.ejmech.2013.10.030

M3 - Article

C2 - 24185377

AN - SCOPUS:84886735069

SN - 0223-5234

VL - 70

SP - 469

EP - 476

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

ER -

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

Abstract

Keywords

UN SDGs

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