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ChemicalBook--->CAS DataBase List--->92478-27-8

92478-27-8

92478-27-8 Structure

92478-27-8 Structure
IdentificationBack Directory
[Name]

Morinidazole
[CAS]

92478-27-8
[Synonyms]

Morinidazole
1-(2-methyl-5-nitro-1H-imidazol-1-yl)-3-morpholinopropan-2-ol
4-Morpholineethanol, α-[(2-methyl-5-nitro-1H-imidazol-1-yl)methyl]-
alpha-[(2-Methyl-5-nitro-1H-imidazol-1-yl)methyl]-4-morpholineethanol
[Molecular Formula]

C11H18N4O4
[MDL Number]

MFCD28386297
[MOL File]

92478-27-8.mol
[Molecular Weight]

270.29
Chemical PropertiesBack Directory
[Boiling point ]

521.4±50.0 °C(Predicted)
[density ]

1.44±0.1 g/cm3(Predicted)
[storage temp. ]

Store at -20°C
[solubility ]

DMSO : ≥ 100 mg/mL (369.97 mM)
[form ]

Solid
[pka]

14.14±0.20(Predicted)
[color ]

White to off-white
Hazard InformationBack Directory
[Description]

Morinidazole (邁靈達(dá)®), 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.

Synthesis_92478-27-8

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