92478-27-8

Basic information

• Product Name: Morinidazole
• Synonyms: Morinidazole;alpha-[(2-Methyl-5-nitro-1H-imidazol-1-yl)methyl]-4-morpholineethanol
• CAS NO: 92478-27-8
• Molecular Formula: C11H18N4O4
• Molecular Weight: 270.28502
• Mol File: 92478-27-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 521.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.44±0.1 g/cm3(Predicted)
• PKA: 14.14±0.20(Predicted)
• CAS DataBase Reference: Morinidazole(CAS DataBase Reference)
• NIST Chemistry Reference: Morinidazole(92478-27-8)
• EPA Substance Registry System: Morinidazole(92478-27-8)

Safety Data

• Hazardous Substances Data: 92478-27-8(Hazardous Substances Data)

Usage

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.

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.

Upstream product

• 110-91-8 morpholine 
• 16773-52-7 (±)-2-methyl-5-nitro-1-(oxiran-2-ylmethyl)-1H-imidazole 
• 16773-42-5 ornidazole 

Relevant articles and documents

Nitroimidazole derivative, preparation method and applications thereof

The invention relates to a nitroimidazole derivative, a preparation method and applications thereof, wherein specifically the compound has a structure represented by a formula I, and various groups and various substituents are defined in the specification. The invention further discloses a preparation method of the compound and applications of the compound in prevention, relieve and/or treatment of diseases caused by anaerobic bacteria infection.

2-Methyl-4/5-nitroimidazole derivatives potentiated against sexually transmitted Trichomonas: Design, synthesis, biology and 3D-QSAR study

Trichomoniasis is the most prevalent, non-viral sexually transmitted diseases (STD) caused by amitochondriate protozoan Trichomonas vaginalis. Increased resistance of T.?vaginalis to the marketed drug Metronidazole necessitates the development of newer chemical entities. A library of sixty 2-methyl-4/5-nitroimidazole derivatives was synthesized via nucleophilic ring opening reaction of epoxide and the efficacies against drug-susceptible and -resistant Trichomonas vaginalis were evaluated. All the molecules except two were found to be active against both susceptible and resistant strains with MICs ranging 8.55–336.70?μM and 28.80–1445.08?μM, respectively. Most of the compounds were remarkably more effective than the standard Metronidazole. This study analyzes the in?vitro and in?vivo activities of the new 5-nitroimidazoles, which were found to be safe against human cervical HeLa cells with good selectivity index. The exploration of SAR by the synthesis of four different prototypes and 3D-QSAR study has shown the importance of prototype 1 over other prototypes.