(Z)-5-(2-Naphthylmethylene)-4-oxo-2-thioxo-1,3-thiazolidine-3-acetic Acid Dimethyl Sulfoxide Solvate

The title acid (1-H-NOTA), as well as its methoxy derivative (1-OCH₃-NOTA), exhibit aldose reductase (AR) inhibitor activity and co-crystallize with dimethyl sulfoxide (DMSO), i.e. C₁₆H₁₁NO₃S₂.C₂H₆OS. The skeleton of 1-H-NOTA is highly planar, except for the acetic acid group. This conformation confers on this molecule a geometry that complements that of the AR active pocket. 1-H-NOTA molecules are held together by van der Waals and ring-to-ring interactions. The stability of the crystal is enhanced by an O—H...O hydrogen bond [O...O 2.554 (5) Å] which links the DMSO to 1-H-NOTA through its carboxy group.

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