Abstract: The 2-arylsulfonylaminobenzothiazole derivatives 1-27 were prepared using a one step reaction. The in vitro inhibitory activity of the compounds against protein tyrosine phosphatase 1B (PTP-1B) was evaluated. Compounds 4 and 16 are rapid reversible (mixed-type) inhibitors of PTP-1B with IC(50) values in the low micromolar range. The most active compounds (4 and 16) were docked into the crystal structure of PTP-1B. Docking results indicate potential hydrogen bond interactions between the nitro group in both compounds and the catalytic amino acid residues Arg 221 and Ser 216. Both compounds were evaluated for their in vivo antihyperglycemic activity in a type 2 diabetes mellitus rat model, showing significant lowering of plasma glucose concentration, during the 7h post-intragastric administration.

Synthesis, in vitro and computational studies of protein tyrosine phosphatase 1B inhibition of a small library of 2-arylsulfonylaminobenzothiazoles with antihyperglycemic activity / G. Navarrete-Vasquez; P. Paoli; I. Leon-Rivera; R. Villalobos-Molina; J.L. Medina-Franco; R. Ortiz-Andrade; S. Estrada-Soto; G. Camici; D. Diaz-Coutino; I. Gallardo-Ortiz; K. Martinez-Mayorga; H. Moreno-Diaz. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 1464-3391. - STAMPA. - 17:(2009), pp. 3332-3341. [10.1016/j.bmc.2009.03.042]

Synthesis, in vitro and computational studies of protein tyrosine phosphatase 1B inhibition of a small library of 2-arylsulfonylaminobenzothiazoles with antihyperglycemic activity

PAOLI, PAOLO;CAMICI, GUIDO;
2009

Abstract

Abstract: The 2-arylsulfonylaminobenzothiazole derivatives 1-27 were prepared using a one step reaction. The in vitro inhibitory activity of the compounds against protein tyrosine phosphatase 1B (PTP-1B) was evaluated. Compounds 4 and 16 are rapid reversible (mixed-type) inhibitors of PTP-1B with IC(50) values in the low micromolar range. The most active compounds (4 and 16) were docked into the crystal structure of PTP-1B. Docking results indicate potential hydrogen bond interactions between the nitro group in both compounds and the catalytic amino acid residues Arg 221 and Ser 216. Both compounds were evaluated for their in vivo antihyperglycemic activity in a type 2 diabetes mellitus rat model, showing significant lowering of plasma glucose concentration, during the 7h post-intragastric administration.
2009
17
3332
3341
G. Navarrete-Vasquez; P. Paoli; I. Leon-Rivera; R. Villalobos-Molina; J.L. Medina-Franco; R. Ortiz-Andrade; S. Estrada-Soto; G. Camici; D. Diaz-Coutin...espandi
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/357683
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