3671-47-4

Usage

Structure

Benzimidazole derivative with a fluorine substitution and a trifluoromethyl group on the second carbon atom

Usage

Synthesis of pharmaceuticals and agrochemicals, organic chemistry research

Biological activities

Antiviral, anticancer properties

Potential use

Building block in drug discovery and development

Versatility

Potential applications in various fields of science and technology

InChI:InChI=1/C8H4F4N2/c9-4-1-2-5-6(3-4)14-7(13-5)8(10,11)12/h1-3H,(H,13,14)

Upstream product

• 367-31-7 4-fluoro-1,2-phenylenediamine 
• 76-05-1 trifluoroacetic acid 
• 1522-22-1 1,1,1,5,5,5-hexafluoroacetylacetone 
• 364-78-3 2-nitro-4-fluoroaniline 

Relevant academic research and scientific papers

Fe(OTf)3-catalyzed practical synthesis of 2-trifluoromethylarylimidazoles from o-arylenediamines and hexafluoroacetylacetone

An iron-catalyzed practical synthesis of 2-trifluoromethylarylimidazoles through condensation of o-arylenediamines and hexafluoroacetylacetone followed by intramolecular addition and C–C bond cleavage in one-pot has been developed. A series of title compounds were obtained with up to 99% yield. This method is quite practical and suitable for scalable preparation due to simple experimental procedure and readily available reagents.

Synthesis and antiprotozoal activity of some 2-(trifluoromethyl)-1H- benzimidazole bioisosteres

A series of 2-(trifluoromethyl)-1H-benzimidazole derivatives with various 5- and 6-position bioisosteric substituents (-Cl, -F, -CF3, -CN), namely 1-7, were prepared using a short synthetic route. Each analogue was tested in vitro against the protozoa Giardia intestinalis and Trichomonas vaginalis in comparison with albendazole and metronidazole. Several analogues had IC50 values 1 μM against both species, which make them significantly more potent than either standard. Compound 4 [2,5(6)- bis(trifluoromethyl)-1H-benzimidazole], was 14 times more active than albendazole against T.:vaginalis. This compound (4) also showed moderate antimalarial activity against W2 and D6 strains of Plasmodium falciparum (5.98 and 6.12 μM, respectively). Studying further structure activity relationships through the use of bioisosteric substitution in these benzimidazolic derivatives should provide new leads against protozoal and possibly malarial diseases.

Synthesis of a series of trifluoromethylazoles and determination of pKa of acidic and basic trifluoromethyl heterocycles by 19F NMR spectroscopy

Trifluoroacetylation at the 5-position of 3,4-dihydro-2H-pyran and the 3-position of 4,5-dihydrofuran, followed by treatment with hydrazine, gave 3-(3-trifluoromethyl-1H-pyrazol-4-yl)propanol and 2-(3-trifluoromethyl-1H-pyrazol-4-yl)ethanol, respectively.In the latter case, an intermediate dimer was isolated.Isomeric 2-(3-trifluoromethyl-1H-pyrazol-5-yl)ethanol was formed by reaction of hydrazine with 6-benzyloxy-1,1,1-trifluorohex-3-yn-2-one and deprotection.Reaction of 3-benzyloxypropylamine with 2,5-bis(trifluoromethyl)-1,3,4-oxadiazole, followed by deprotection, afforded 3-propanol.A series of 2-trifluoromethyl-1H-benzimidazoles and 2-trifluoromethyl-3H-imidazopyridines were prepared by condensation of the appropriate ortho-arenediamine with trifluoroacetic acid.Analysis of the 19F NMR spectra of the trifluoromethylazoles and of 3-trifluoromethylpyridine in aqueous solution at different pHs enabled determination of pKa values.All the compounds evaluated had one or more pKa between 1 and 13, except the triazole.Several compounds were identified as having potential use in measuring pH in biological media by 19F NMR spectroscopy.