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Keywords
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piroxicam, Silyl derivatives, Lipophilicity, MD simulation, structural properties
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Abstract
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The painkiller piroxicam was examined in this research study. Two derivatives dimethyl-tert-butyl-silyloxy and triethyl silyloxy
piroxicam were synthesized to improve the drug’s lipophilicity and permeability. Thin layer chromatography was used
to separate silylated derivatives, and SN2 was the reaction mechanism. FT-IR and 1H-NMR spectroscopy were used to
identify the produced compounds. Reverse phase high performance liquid chromatography (RP-HPLC) was employed
to examine the lipophilicity of the silylated derivatives of piroxicam. Due to the non-polar nature of the column used
in this device and the polarity of piroxicam and its derivatives, the retention time of silylated derivatives was longer in
the column compared to the original piroxicam, due to the inherent nature of these materials which have high non
polar properties. The results show an acceptable increase in the lipophilicity of the silylated derivatives compared to
piroxicam. To evaluate the hydrophobic properties of drugs e.g., piroxicam and the Silyl derivatives of piroxicam, the distribution
of the species around the drugs were investigated in a Water/Octanol mixture using molecular dynamics simulation
(MDS). Results of the radial distribution functions (RDFs) and continuous hydrogen bond networks suggest a
favorable interaction between Octanol molecules and the silyl derivatives of piroxicam compared to piroxicam.
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