167993-21-7

Usage

Uses

Used in Pharmaceutical Industry:
BOC-L-2-Trifluoromethylphe is used as a key building block for the development of novel pharmaceutical compounds. Its trifluoromethyl group contributes to the improved metabolic stability and lipophilicity of the molecules, which can lead to enhanced drug efficacy and bioavailability.
Used in Medicinal Chemistry:
BOC-L-2-Trifluoromethylphe is employed as a crucial component in the synthesis of new drug candidates. Its unique structural features allow for the exploration of various chemical modifications, potentially leading to the discovery of innovative therapeutic agents.
Used in Chemical Biology:
BOC-L-2-Trifluoromethylphe is used as a versatile building block in the creation of bioactive molecules for chemical biology research. Its incorporation into peptide sequences can provide insights into the structure-activity relationships of biologically relevant compounds, facilitating the understanding of molecular interactions and the development of targeted therapeutic strategies.

InChI:InChI=1/C15H18F3NO4/c1-14(2,3)23-13(22)19-11(12(20)21)8-9-6-4-5-7-10(9)15(16,17)18/h4-7,11H,8H2,1-3H3,(H,19,22)(H,20,21)/t11-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 130930-49-3 (2S)-2-amino-3-[2-(trifluoromethyl)phenyl]propanoic acid 

Downstream Products

• 1067613-16-4 N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-3-fluoro-4-(1-methyl-1H-pyrazol-5-yl)benzamide 
• 1067612-65-0 1,1-dimethylethyl {(2S)-2-({[5-(1-methyl-1H-pyrazol-5-yl)-2-pyridinyl]carbonyl}amino)-3-[2-(trifluoromethyl)phenyl]propyl}carbamate 
• 1067612-62-7 C₁₆H₁₅BrF₃N₃O 
• 1067612-59-2 1,1-dimethylethyl {(2S)-2-{[(5-bromo-2-pyridinyl)carbonyl]amino}-3-[2-(trifluoromethyl)phenyl]propyl}carbamate 
• 1067612-56-9 5-bromo-N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-2-pyridinecarboxamide 
• 1067613-95-9 N-((1S)-2-amino-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-4-(1-methyl-1H-1,2,4-triazol-5-yl)benzamide 
• 1067613-99-3 N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-4-(1-methyl-1H-1,2,4-triazol-5-yl)benzamide 
• 1067613-73-3 3-bromo-N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-4-(1-methyl-1H-pyrazol-5-yl)benzamide 
• 1067613-55-1 4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-3-fluorobenzamide 
• 1044851-55-9 2-{(2S)-2-amino-3-[2-(trifluoromethyl)phenyl]propyl}-1H-isoindole-1,3(2H)-dione hydrochloride 

Relevant academic research and scientific papers

2H-1,2,3-Triazole-Based Dipeptidyl Nitriles: Potent, Selective, and Trypanocidal Rhodesain Inhibitors by Structure-Based Design

Macrocyclic inhibitors of rhodesain (RD), a parasitic cysteine protease and drug target for the treatment of human African trypanosomiasis, have shown low metabolic stability at the macrocyclic ether bridge. A series of acyclic dipeptidyl nitriles was developed using structure-based design (PDB ID: 6EX8). The selectivity against the closely related cysteine protease human cathepsin L (hCatL) was substantially improved, up to 507-fold. In the S2 pocket, 3,4-dichlorophenylalanine residues provided high trypanocidal activities. In the S3 pocket, aromatic residues provided enhanced selectivity against hCatL. RD inhibition (Ki values) and in vitro cell-growth of Trypanosoma brucei rhodesiense (IC50 values) were measured in the nanomolar range. Triazole-based ligands, obtained by a safe, gram-scale flow production of ethyl 1H-1,2,3-triazole-4-carboxylate, showed excellent metabolic stability in human liver microsomes and in vivo half-lives of up to 1.53 h in mice. When orally administered to infected mice, parasitaemia was reduced but without complete removal of the parasites.