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1 Polish Journal of Chemistry

1 1999

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Molecular structure of two 1-O-acylglycosyl esters of diclofenac

Kołodziejczyk E., Suwińska K., Kozioł A., Enright G., Borowiecka J.

Polish Journal of Chemistry

1999

vol. 73 nr 2

367-376

The molecular structure of 8 and 9 has been determined by a single-crystal X-ray analysis. Both chiral esters are derivatives of the non-steroidal anti-inflammatory drug diclofenac (1), and have physicochemical properties of potential prodrug. Comparison of the geometry of 2-[(2,6-dichlorophenyl)amino]phenylacetate fragment, observed in eighteen solid-state structures, shows limited flexibility of 1. Two rotations around bonds linking the o-phenyl ring with the carboxyl and dichlorophenyl groups change their relative orientation, but both groups are nearly perpendicular to the o-phenyl plane. The amino group is involved exclusively in intramolecular contacts.