59729-37-2

Usage

Uses

Used in Pharmaceutical Industry:
Fexinidazole is used as an antitrypanosomal agent for the treatment of African trypanosomiasis, a disease caused by the parasite Trypanosoma brucei gambiense. This medication plays a crucial role in combating this life-threatening condition, which is prevalent in sub-Saharan Africa.
Additionally, Fexinidazole is used as a medication against the main species responsible for visceral and cutaneous New World leishmaniasis. These are parasitic diseases caused by the Leishmania genus, which can lead to severe health complications if left untreated. Fexinidazole's effectiveness in treating these conditions highlights its importance in the field of tropical medicine and infectious diseases.

InChI:InChI=1/C12H13N3O3S/c1-14-11(13-7-12(14)15(16)17)8-18-9-3-5-10(19-2)6-4-9/h3-7H,8H2,1-2H3

Upstream product

• 77-78-1 dimethyl sulfate 
• 67343-65-1 1-methyl-5-nitro-2-(4-thiocyanato-phenoxymethyl)-1H-imidazole 
• 1610877-02-5 1-methyl-2-(4-methylmercaptophenyloxymethyl)-5-nitroimidazole hydrochloride 
• 1073-72-9 4-hydroxythioanisole 
• 86990-28-5 2-(methanesulphonyloxymethyl)-1-methyl-5-nitroimidazole 
• 108-95-2 phenol 
• 936-05-0 1-methyl-2-hydroxymethyl-5-nitroimidazole 
• 6905-07-3 2-(chloromethyl)-1-methyl-5-nitroimidazole 

Downstream Products

• 1610877-02-5 1-methyl-2-(4-methylmercaptophenyloxymethyl)-5-nitroimidazole hydrochloride 
• 62351-99-9 1-methyl-2-(4-methylsulfinylphenoxymethyl)-5-nitroimidazole 

Relevant academic research and scientific papers

Silver(I)-Promoted ipso-Nitration of Carboxylic Acids by Nitronium Tetrafluoroborate

A novel and efficient method for the regioselective nitration of a series of aliphatic and aromatic carboxylic acids to their corresponding nitro compounds using nitronium tetrafluoroborate and silver carbonate in dimethylacetamide has been described. This transformation is believed to proceed via the alkyl-silver or aryl-silver intermediate, which subsequently reacts with the nitronium ion to form nitro substances. Mild reaction conditions, tolerant of a broad range of functional groups, and formation of only the ipso-nitrated products are the key features of this methodology when compared to known methods for syntheses of nitroalkyls and nitroarenes.

METHOD FOR PREPARING PHENYLOXYMETHYL-NITRO-IMIDAZOLE DERIVATIVES AND USE OF SAME

Fexinidazole is prepared according to a method which comprises the following steps: a) reacting 1-methyl-2-hydroxymethyl-5-nitro-imidazole with methanesulfonyl chloride in the presence of a suspension of powdered alkaline carbonate in an anhydrous organic solvent suitable for performing nucleophile substitution reactions; b) adding to the resulting reaction medium a solution of 4-methyl-mercapto-phenol in the same organic solvent as referred to in step a); c) separating fexinidazole from the reaction mixture as its hydrochloride salt and d) converting said hydrochloride salt into fexinidazole and optionally, purifying the latter.

Compounds containing 2-substituted imidazole ring for treatment against human African trypanosomiasis

A series of compounds containing 2-substituted imidazoles has been synthesized from imidazole and tested for its biological activity against human African trypanosomiasis (HAT). The 2-substituted 5-nitroimidazoles such as fexinidazole (7a) and 1-[4-(1-methyl-5-nitro-1H-imidazol-2-ylmethoxy)-pyridin-2- yl-piperazine (9e) exhibited potent activity against T. brucei in vitro with low cytotoxicity and good solubility. The presence of the NO2 group at the 5-position of the imidazole ring in 2-substituted imidazoles is the crucial factor to inhibit T. brucei.

Chemotherapeutically active nitro compounds. 4,5-Nitroimidazoles (part III)

More than 100 1-methyl-5-nitroimidazoles substituted in the 2-position via an oxymethyl group were synthesized and their structure-activity relationship toward various protozoa was investigated. Among the derivatives substituted with an aromatic radical there are most of the compounds which are highly effective against trichomonads; 9 preparations are superior to tinidazole and 29 are superior to metronidazole in mice infected with Trichomonas fetus and 9 compounds exhibit a better effect than metronidazole in golden hamsters intrahepatically infected with Entamoeba histolytica. In the same series one dialkylamino-acetamide derivative shows excellent trypanocidal activity in the NMRI mouse, but this effect is limited to Trypanosoma brucei; 12 preparations developed a trypanocidal effect only after relatively high doses; their range of efficacy included Trypanosoma cruzi, among others, after repeated treatment. Of the carboxyl acid, carbamic acid and sulphonic acid esters synthesized, only the already known group of carbamic acid esters possess a pronounced antiprotozoal effect. Among the preparations substituted with a heterocyclic radical some of the pyridine derivatives proved to have distinct trichomonacidal activity. The influence of the type of substitution and the stability of the C-X bond in 2-substituted 5-nitroimidazoles of all compounds synthesized so far (I-III, 4th report) are discussed in 2 tables.

1-Methyl-2-(phenyl-oxymethyl)-5-nitro-imidazoles and process for their manufacture

1-Methyl-2-(phenyl-oxymethyl)-5-nitro-imidazoles and a process for preparing them are disclosed. The compounds of the invention are suitable for the treatment of protozoal diseases caused in humans and animals and of bacteria and fungi.