Studies On Synthesis Of Optically Pure Secnidazole

Secnidazole is a kind of 5-nitroimidazole. It is active in the treatment of anaerobic protozoan and bacterial infections, which were found particularly effective in the treatment of Amoebiasis, Giardiasis,Trichomoniasis and bacterial vaginosis. There is a chiral carbon in the secnidazole's geometry molecular , racemic secnidazole is used on clinical at the present time. Drug's chirality is straightly referred to drug's pharmacological action ,clinical performance, side- effect, the action of drug's duration. In many cases, racemic drug's single antipode has different curative effect, sometimes it even has adverse action. The application and preparation of chiral drugs is one of the orientation of medicine development of industry, So it is meaningful something to study on chiral 5-nitroimidazole.This paper studied on the chiral secnidazole's preparation method . S-(+)-secnidazole and R-(-)-secnidazole were made. Reaction process conditions and important intermediate product (chiral Propane 1,2-cyclic sulfate)' preparation process are groped.Their structure were characterized by IR, ¹H NMR,¹³C NMR,MS. Their optical rotation were measured by polarimeter. experimental result indicated:(1) In the process of secnidazole preparation, acetoxymethyl primely prevented 3-N atom on imidazole from Propane 1,2-cyclic sulfate ' attack.(2) using chiral Propane 1,2-cyclic sulfate and 4-nitroimidazoles can successfully make chiral secnidazole.This paper's result of chiral secnidazole's preparation method and process conditions has guiding significance and reference value for industrial production and study on synthesis of other chiral 5-nitroimidazole .