Synthesis of α-CF3-containing triazolyl amino acids as potential neurotransmitters via click-reaction

• Published in: Journal of fluorine chemistry Vol. 175; pp. 60 - 67
• Main Authors: Vorobyeva, Daria V., Peregudov, Alexander S., Röschenthaler, Gerd-V., Osipov, Sergey N.
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.07.2015; Elsevier
• Subjects: 1,2,3-Triazoles; 1,3-Dipolar cycloaddition; Amino acids; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Cu-catalysis; Physical Sciences; Science & Technology; XUBSJDUFFCQWIF-WSAWMEMJSA-N; 1,3-Dipolar cycloaddition; NHJHSDZYUKPKQK-NVHKAFQKSA-N; FOUHCHYOKHRJTR-ZZHFZYNASA-N; KWLUZHGSPXDSRV-FUKCDUGKSA-N; MRFLHJXQRTYIKH-BVVIDWAXSA-N; DJYCBINMQKHSTO-YDNXMHBPSA-N; Amino acids; JRPXTZGFAIELDO-YXWRBFHGSA-N; 1,2,3-Triazoles; FAGASYYRISHZPS-CISYCMJJSA-N; UFDFUDYQWQPLLY-UHFFFAOYSA-N; YNSSXKPFDPJOFI-APDXDRDNSA-N; OXQNBBVYAOWWNA-XGLRFROISA-N; PBSKROLFXNFRKA-PIJUOJQZSA-N; OAKYUPZALRSQJS-AJZOCDQUSA-N; SYFPJYKLWRCJOH-DJZRFWRSSA-N; AZRDESBXGYOQAY-HSLMYDHPSA-N; HCCLQDMSLNWTCM-FVRDMJKUSA-N; BYYFTWRQBADLRN-KNVGNIICSA-N; XQOZPORLEUSQRG-WHUIICBVSA-N; ZQCILLYYBSWODF-BJQOMGFOSA-N; Cu-catalysis; QFXNCPYYOLEPJJ-UHFFFAOYSA-N; QSBAREPRMRZRDZ-QHELBMECSA-N; JULNCTGDQLECIH-PBVYKCSPSA-N; POQOWDRIAJABMB-UHFFFAOYSA-N; PNLFEAPAIBWQON-KTQQKIMGSA-N; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; PHARMACOLOGY; CHEMISTRY; FLUORINE; GLUTAMATE-RECEPTOR ANTAGONISTS; STRATEGIES; MOMENTS
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2015.03.012

A convenient route to novel α-CF3-containing triazolyl α-amino acids and α-aminophosphonates as potential neurotransmitters has been developed. •α-CF3-containing triazolyl α-amino acid derivatives as potential neurotransmitters.•Synthesis of homologous azaglutamate derivatives.•The methods for the selective removal of protective groups have been developed. A convenient route to novel α-CF3-containing triazolyl α-amino acids and α-aminophosphonates with 3-alanyl substituent in heterocyclic moiety and distal OH-group, which can imitate the active elements of glutamate-based receptors, using Cu-catalyzed 1,3-dipolar cycloaddition of different α-azido acids and α-azido esters to functionalized acetylenes has been developed.