Nitrophenyl derivatives were recently discovered as a new class of ALR2 inhibitors by means of docking and database screening of the National Cancer Institute database of organic molecules. The nitro group was predicted to bind to the Tyr48 and His110 active site residues of the enzyme, the site where acidic ALR2 inhibitors such as carboxylic acids bind in their anionic form. Given the novelty of these compounds, we decided to expand their structure-activity relationships by synthesizing and testing a series of derivatives and the corresponding compounds having a carboxylic group instead of the nitro moiety; the results obtained were rationalized by means of docking and molecular dynamics simulations. On the whole there is an agreement between inhibitory data and the results of molecular modeling experiments, supporting the hypothesized binding mode of these compounds.

Nitrophenyl derivatives as Aldose Reductase inhibitors / Costantino, Luca; A. M., Ferrari; Gamberini, Maria Cristina; Rastelli, Giulio. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 0968-0896. - STAMPA. - 10:(2002), pp. 3923-3931. [10.1016/S0968-0896(02)00318-8]

Nitrophenyl derivatives as Aldose Reductase inhibitors

COSTANTINO, Luca;GAMBERINI, Maria Cristina;RASTELLI, Giulio
2002

Abstract

Nitrophenyl derivatives were recently discovered as a new class of ALR2 inhibitors by means of docking and database screening of the National Cancer Institute database of organic molecules. The nitro group was predicted to bind to the Tyr48 and His110 active site residues of the enzyme, the site where acidic ALR2 inhibitors such as carboxylic acids bind in their anionic form. Given the novelty of these compounds, we decided to expand their structure-activity relationships by synthesizing and testing a series of derivatives and the corresponding compounds having a carboxylic group instead of the nitro moiety; the results obtained were rationalized by means of docking and molecular dynamics simulations. On the whole there is an agreement between inhibitory data and the results of molecular modeling experiments, supporting the hypothesized binding mode of these compounds.
2002
10
3923
3931
Nitrophenyl derivatives as Aldose Reductase inhibitors / Costantino, Luca; A. M., Ferrari; Gamberini, Maria Cristina; Rastelli, Giulio. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 0968-0896. - STAMPA. - 10:(2002), pp. 3923-3931. [10.1016/S0968-0896(02)00318-8]
Costantino, Luca; A. M., Ferrari; Gamberini, Maria Cristina; Rastelli, Giulio
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/641848
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