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

The title compound (1-OCH₃-NOTA) is a potent aldose reductase (AR) inhibitor. It is found to cocrystallize with the solvent dimethyl sulfoxide (DMSO), i.e. C₁₇H₁₃NO₄S₂.C₂H₆OS. The skeleton of 1-OCH₃-NOTA is highly planar, except for the acetic acid group and the methoxy substituent. This particular conformation confers on this molecule an optimum geometrical complement to the shape of the aldose reductase (AR) active pocket. Molecules of 1-OCH₃-NOTA, related by a centre of symmetry in the crystal structure of the DMSO solvate, are held together by van der Waals and ring-to-ring interactions. The stability of the crystal is enhanced by a hydrogen bond which links the DMSO molecule to 1-OCH₃-NOTA through its carboxyl group.

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