Synthesis and antioxidant evaluation of enantiomerically pure bis-(1,2,3-triazolylmethyl)amino esters from modified α-amino acids.
The efforts for synthesis of enantiomerically pure bis-(1,2,3-triazolylmethyl)amino esters 6 are reported in good yields from an in situ generated α-azidomethyl ketone. Optimum experimental conditions were established for preparation of α-halomethyl ketones 10 and α-N,N-dipropargylamino esters 11, all derived from α-amino acids. The starting materials reacted under conventional click chemistry conditions, revealing a specific reactivity of bromomethyl ketones over chloromethyl ketones. The antioxidant activity of compounds 6 was assayed by DPPH method. The compound 6c with an IC50 of 75.57 ± 1.74 μg mL(-1) was the most active. Technically, this methodology allows the preparation of a combinatorial library of analogues with different structural characteristics depending on the nature of the modified α-amino acids employed in the synthesis.
Facultad de Ingeniería, Universidad Autónoma de Sinaloa, Boulevard de las Américas S/N, 80040 Culiacán, SIN, Mexico.
Juan I
JI
Sarmiento-Sánchez
Centro de Graduados e Investigación del Instituto Tecnológico de Tijuana, Boulevard Alberto Limón Padilla S/N, Apdo. Postal 1166, 22500 Tijuana, BC, Mexico.
Adrián
A
Ochoa-Terán
Centro de Graduados e Investigación del Instituto Tecnológico de Tijuana, Boulevard Alberto Limón Padilla S/N, Apdo. Postal 1166, 22500 Tijuana, BC, Mexico.
Ignacio A
IA
Rivero
D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D057930:Click Chemistry; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D000975:Antioxidants; D004952:Esters; D007659:Ketones