A series of 2,4-dioxo-5-(2-naphthylmethylene)-3-thiazolidineacetic acids and 2-thioxo analogues have been prepared as aldose reductase inhibitors. In vitro inhibitory activities of bovine lens aldose reductase were determined by a conventional method. 1-Naphthyl-substituted derivatives of the 2-thioxo series were the more potent inhibitors (IC50 congruent with 10 nM) with similar activity to that of Epalrestat. Structural analysis, especially by X-ray crystallography of two selected compounds, and molecular modeling comparisons with Zopolrestat were performed. These results provide explanations of the good activity of the inhibitor, the preference for 1-naphthyl-substituted compounds, and the nature of molecular interactions in these systems.

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A series of 3‐carboxylic derivatives of disubstituted 1,5‐benzodiazepines (5–9) was synthesized by hetero‐cyclisation from 1,2‐diaminobenzene (1) with dibenzoylmethane (2) followed by bromination on position 3 and by introduction of the carboxylic group or introduction of the malonic moiety. Reduction of the hetero‐cycle gave the perhydro derivative diethyl (2,4‐diphenyl‐1,2,4,5‐tetrahydro‐3H‐1,5‐benzodiazepin‐3‐yl)malonate (9).

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