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2 Polish Journal of Chemistry

2 1999

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New derivatives of A- and B-dithiophosphates of 2-bromo-2-deoxy sugars

Borowiecka J.

Polish Journal of Chemistry

1999

vol. 73 nr 5

793-798

New derivatives of 2-bromo-2deoxy hexopyranose, a and b-glycosyl dithiophosphates 6-11, were synthesized by three methods: (A) by glycosylation of alkyl salts 1-3 of phosphorodithio acids with a-1,2-D-gluco and a-1,2-D-manno dibromides 4,5; (B) by reaction of 4 or 5 with free phosphorodithio acids 12-14 activated by Lewis acid; (C) by addition of dithioacids 12-14 to 2-bromo-D-glucal 15.

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.