113193-72-9

Upstream product

• 288-32-4 1H-imidazole 
• 3946-29-0 3,4'-Dichloropropiophenone 
• 1798-83-0 1-(4-chlorophenyl)-3-dimethylamino-propan-1-one hydrochloride 
• 2234-16-4 1-(2,4-dichlorophenyl)ethan-1-one 
• 99-91-2 para-chloroacetophenone 

Downstream Products

• 1563040-16-3 (E)-1-(4-chlorophenyl)-3-(1H-imidazol-1-yl)propan-1-one O-4-chlorobenzoyl oxime 
• 1187041-16-2 (1E)-1-(4-chlorophenyl)-N-hydroxy-3-(1H-imidazol-1-yl)propan-1-imine 
• 149490-95-9 [(2R,4R)-2-(4-Chloro-phenyl)-2-(2-imidazol-1-yl-ethyl)-[1,3]dioxolan-4-yl]-methanethiol 
• 149490-95-9 [(2R,4S)-2-(4-Chloro-phenyl)-2-(2-imidazol-1-yl-ethyl)-[1,3]dioxolan-4-yl]-methanethiol 
• 149490-97-1 [(2S,5S)-2-(4-Chloro-phenyl)-2-(2-imidazol-1-yl-ethyl)-[1,3]oxathiolan-5-yl]-methanol 
• 149490-97-1 [(2S,5R)-2-(4-Chloro-phenyl)-2-(2-imidazol-1-yl-ethyl)-[1,3]oxathiolan-5-yl]-methanol 

Relevant academic research and scientific papers

Design and synthesis of Mannich base-type derivatives containing imidazole and benzimidazole as lead compounds for drug discovery in Chagas Disease

The protozoan parasite Trypanosoma cruzi is the causative agent of Chagas disease, the most important parasitic infection in Latin America. The only treatments currently available are nitro-derivative drugs that are characterised by high toxicity and limited efficacy. Therefore, there is an urgent need for more effective, less toxic therapeutic agents. We have previously identified the potential for Mannich base derivatives as novel inhibitors of this parasite. To further explore this family of compounds, we synthesised a panel of 69 new analogues, based on multi-parametric structure-activity relationships, which allowed optimization of both anti-parasitic activity, physicochemical parameters and ADME properties. Additionally, we optimized our in vitro screening approaches against all three developmental forms of the parasite, allowing us to discard the least effective and trypanostatic derivatives at an early stage. We ultimately identified derivative 3c, which demonstrated excellent trypanocidal properties, and a synergistic mode of action against trypomastigotes in combination with the reference drug benznidazole. Both its druggability and low-cost production make this derivative a promising candidate for the preclinical, in vivo assays of the Chagas disease drug-discovery pipeline.

In vitro anti-Candida activity of certain new 3-(1H-Imidazol-1-yl)propan-1- one oxime esters

Anti-Candida activities of certain new oximes 4a-d and their respective aromatic esters 5a-l are reported. The tested compounds 4a-d and 5a-l exhibited better anti-Candida profiles than fluconazole. Compound 5j, namely (E)-3-(1H-imidazol-1-yl)-1- phenylpropan-1-one O-4-chlorobenzoyl oxime emerged as the most active congener, with a MIC value of 0.0054 μmol/mL being more potent than both fluconazole (MIC > 1.6325 μmol/mL) and miconazole (MIC value = 0.0188 μmol/mL) as a new anti-Candida albicans agent.

Reaction of Aromatic Ketones with 3-Mercapto-1,2-propanediol. Synthesis of cis- and trans-2-Alkyl-2-aryl-(1,3-oxathiolane-5-methanols and 1,3-dioxolane-4-methanethiols)

Aromatic ketones react with 3-mercapto-1,2-propanediol (1) in refluxing benzene under the catalytic influence of sulfonic acid and with azeotropic removal of water to yield a mixture comprised predominantly of cis- and trans-2-alkyl-2-aryl-1,3-oxathiolane

A CONVENIENT SYNTHESIS OF 1H-1,2,4-TRIAZOL-1-YL-PROPAN-3-ONE DERIVATIVES BY MODIFIED MANNICH REACTION

1H-1,2,4-Triazol-yl-propan-3-ones were synthesized regioselectively using a modified Mannich reaction.Reactions of enones and Mannich bases with imidazole are also described.