Description
Morinidazole (迈灵达®), discovered and developed by Jiangsu
Hansoh Pharmaceutical, was approved by the CFDA in February
2014. Morinidazole is a novel third generation 5-nitroimidazoleclass
antimicrobial agent indicated for the treatment of amoebiasis
and anaerobic bacterial infections including appendicitis and pelvic
inflammatory disease. 5-Nitroimidazole antimicrobial drugs
act via nitroreduction of the molecules in the pathogens; as an
analog of metronidazole, morinidazole exhibits greater antiparasitic
potency against Trichomonas vaginalis and amoebic protozoa,
and relatively weaker toxicity in vitro and in preclinical studies
compared with metronidazole.
Uses
Morinidazole is a useful research chemical compound used as a microbial drug against Trichomoniasis, a non-viral sexually transmitted disease.
Synthesis
The strategy to prepare morinidazole, which exists as a racemate,
overlaps with that of ornidazole. Commercially available epichlorohydrin (176) was
reacted with commercial 2-methyl-5-nitro-1H-imidazole (175) to
provide ornidazole 177 in 51% yield. Next, epoxide 178 was
obtained in 84% through the treatment of ornidazole 177 with
TBAF in aqueous sodium hydroxide. Subsequently, the ring of
epoxide 178 was opened with the treatment of morpholine (179)
to afford morinidazole (XX) in 75% yield.
