title: Ruthenium-catalyzed synthesis of 5-amino-1,2,3-triazole-4-carboxylates for triazole-based scaffolds: beyond the dimroth rearrangement.
abstract: The 5-amino-1,2,3-triazole-4-carboxylic acid is a suitable molecule for the preparation of collections of peptidomimetics or biologically active compounds based on the triazole scaffold. However, its chemistry may be influenced by the possibility of undergoing the Dimroth rearrangement. To overcome this problem, a protocol based on the ruthenium-catalyzed cycloaddition of N-Boc ynamides with azides has been developed to give a protected version of this triazole amino acid. When aryl or alkyl azides are reacted with N-Boc-aminopropiolates or arylynamides, the cycloaddition occurs with complete regiocontrol, while N-Boc-alkyl ynamides yield a mixture of regioisomers. The prepared amino acids were employed for the preparation of triazole-containing dipeptides having the structural motives typical of turn inducers. In addition, triazoles active as HSP90 inhibitors (as compound 41, IC50 = 29 nM) were synthesized.
authors: Dipartimento di Biotecnologie, Chimica e Farmacia, Università di Siena , Via A. Moro 2, 53100 Siena, Italy.
authors: Serena
authors: S
authors: Ferrini
authors: Jay Zumbar
authors: JZ
authors: Chandanshive
authors: Stefano
authors: S
authors: Lena
authors: Mauro
authors: M
authors: Comes Franchini
authors: Giuseppe
authors: G
authors: Giannini
authors: Andrea
authors: A
authors: Tafi
authors: Maurizio
authors: M
authors: Taddei
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D004151:Dipeptides / Q000737:chemistry*; D018841:HSP90 Heat-Shock Proteins / Q000819:agonists / Q000037:antagonists & inhibitors / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D057786:Peptidomimetics / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: C000601914:5-amino-1,2,3-triazole-4-carboxylic acid; D000596:Amino Acids; D001386:Azides; D002264:Carboxylic Acids; D004151:Dipeptides; D018841:HSP90 Heat-Shock Proteins; D057786:Peptidomimetics; D014230:Triazoles; D012428:Ruthenium