Antidiabetic activity of N-(6-substituted-1,3-benzothiazol-2-yl)benzenesulfonamides

Hermenegilda Moreno-Díaz; Rafael Villalobos-Molina; Rolffy Ortiz-Andrade; Daniel Díaz-Coutiño; Jose Luis Medina-Franco; Scott P Webster; Margaret Binnie; Samuel Estrada-Soto; Maximiliano Ibarra-Barajas; Ismael León-Rivera; Gabriel Navarrete-Vázquez

doi:10.1016/j.bmcl.2008.03.086

Antidiabetic activity of N-(6-substituted-1,3-benzothiazol-2-yl)benzenesulfonamides

Hermenegilda Moreno-Díaz, Rafael Villalobos-Molina, Rolffy Ortiz-Andrade, Daniel Díaz-Coutiño, Jose Luis Medina-Franco, Scott P Webster, Margaret Binnie, Samuel Estrada-Soto, Maximiliano Ibarra-Barajas, Ismael León-Rivera, Gabriel Navarrete-Vázquez

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

Abstract / Description of output

N-(6-Substituted-1,3-benzothiazol-2-yl)benzenesulfonamide derivatives 1-8 were synthesized and evaluated for their in vivo antidiabetic activity in a non-insulin-dependent diabetes mellitus rat model. Several compounds synthesized showed significant lowering of plasma glucose level in this model. As a possible mode of action, the compounds were in vitro evaluated as 11beta-hydroxysteroid dehydrogenase type 1 (11beta-HSD1) inhibitors. The most active compounds (3 and 4) were docked into the crystal structure of 11beta-HSD1. Docking results indicate potential hydrogen bond interactions with catalytic amino acid residues.

Original language	English
Pages (from-to)	2871-2877
Number of pages	7
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	18
Issue number	9
DOIs	https://doi.org/10.1016/j.bmcl.2008.03.086
Publication status	Published - 2008

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Moreno-Díaz, H., Villalobos-Molina, R., Ortiz-Andrade, R., Díaz-Coutiño, D., Medina-Franco, J. L., Webster, S. P., Binnie, M., Estrada-Soto, S., Ibarra-Barajas, M., León-Rivera, I., & Navarrete-Vázquez, G. (2008). Antidiabetic activity of N-(6-substituted-1,3-benzothiazol-2-yl)benzenesulfonamides. Bioorganic & Medicinal Chemistry Letters, 18(9), 2871-2877. https://doi.org/10.1016/j.bmcl.2008.03.086

@article{0c06a715554b40728e7c2dc221c08c6f,

title = "Antidiabetic activity of N-(6-substituted-1,3-benzothiazol-2-yl)benzenesulfonamides",

abstract = "N-(6-Substituted-1,3-benzothiazol-2-yl)benzenesulfonamide derivatives 1-8 were synthesized and evaluated for their in vivo antidiabetic activity in a non-insulin-dependent diabetes mellitus rat model. Several compounds synthesized showed significant lowering of plasma glucose level in this model. As a possible mode of action, the compounds were in vitro evaluated as 11beta-hydroxysteroid dehydrogenase type 1 (11beta-HSD1) inhibitors. The most active compounds (3 and 4) were docked into the crystal structure of 11beta-HSD1. Docking results indicate potential hydrogen bond interactions with catalytic amino acid residues.",

author = "Hermenegilda Moreno-D{\'i}az and Rafael Villalobos-Molina and Rolffy Ortiz-Andrade and Daniel D{\'i}az-Couti{\~n}o and Medina-Franco, {Jose Luis} and Webster, {Scott P} and Margaret Binnie and Samuel Estrada-Soto and Maximiliano Ibarra-Barajas and Ismael Le{\'o}n-Rivera and Gabriel Navarrete-V{\'a}zquez",

year = "2008",

doi = "10.1016/j.bmcl.2008.03.086",

language = "English",

volume = "18",

pages = "2871--2877",

journal = "Bioorganic & Medicinal Chemistry Letters",

publisher = "Elsevier",

number = "9",

}

Moreno-Díaz, H, Villalobos-Molina, R, Ortiz-Andrade, R, Díaz-Coutiño, D, Medina-Franco, JL, Webster, SP, Binnie, M, Estrada-Soto, S, Ibarra-Barajas, M, León-Rivera, I & Navarrete-Vázquez, G 2008, 'Antidiabetic activity of N-(6-substituted-1,3-benzothiazol-2-yl)benzenesulfonamides', Bioorganic & Medicinal Chemistry Letters, vol. 18, no. 9, pp. 2871-2877. https://doi.org/10.1016/j.bmcl.2008.03.086

TY - JOUR

T1 - Antidiabetic activity of N-(6-substituted-1,3-benzothiazol-2-yl)benzenesulfonamides

AU - Moreno-Díaz, Hermenegilda

AU - Villalobos-Molina, Rafael

AU - Ortiz-Andrade, Rolffy

AU - Díaz-Coutiño, Daniel

AU - Medina-Franco, Jose Luis

AU - Webster, Scott P

AU - Binnie, Margaret

AU - Estrada-Soto, Samuel

AU - Ibarra-Barajas, Maximiliano

AU - León-Rivera, Ismael

AU - Navarrete-Vázquez, Gabriel

PY - 2008

Y1 - 2008

N2 - N-(6-Substituted-1,3-benzothiazol-2-yl)benzenesulfonamide derivatives 1-8 were synthesized and evaluated for their in vivo antidiabetic activity in a non-insulin-dependent diabetes mellitus rat model. Several compounds synthesized showed significant lowering of plasma glucose level in this model. As a possible mode of action, the compounds were in vitro evaluated as 11beta-hydroxysteroid dehydrogenase type 1 (11beta-HSD1) inhibitors. The most active compounds (3 and 4) were docked into the crystal structure of 11beta-HSD1. Docking results indicate potential hydrogen bond interactions with catalytic amino acid residues.

AB - N-(6-Substituted-1,3-benzothiazol-2-yl)benzenesulfonamide derivatives 1-8 were synthesized and evaluated for their in vivo antidiabetic activity in a non-insulin-dependent diabetes mellitus rat model. Several compounds synthesized showed significant lowering of plasma glucose level in this model. As a possible mode of action, the compounds were in vitro evaluated as 11beta-hydroxysteroid dehydrogenase type 1 (11beta-HSD1) inhibitors. The most active compounds (3 and 4) were docked into the crystal structure of 11beta-HSD1. Docking results indicate potential hydrogen bond interactions with catalytic amino acid residues.

U2 - 10.1016/j.bmcl.2008.03.086

DO - 10.1016/j.bmcl.2008.03.086

M3 - Article

C2 - 18424136

VL - 18

SP - 2871

EP - 2877

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 9

ER -

Antidiabetic activity of N-(6-substituted-1,3-benzothiazol-2-yl)benzenesulfonamides

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