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Synthesis and antioxidant evaluation of enantiomerically pure bis-(1,2,3-triazolylmethyl)amino esters from modified ?-amino acids.

ABSTRACT: 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 ?-azidomethyl ketone. Optimum experimental conditions were established for preparation of ?-halomethyl ketones 10 and ?-N,N-dipropargylamino esters 11, all derived from ?-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 ?g 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 ?-amino acids employed in the synthesis.

SUBMITTER: Sarmiento-Sanchez JI

PROVIDER: S-EPMC4216715 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

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Synthesis and antioxidant evaluation of enantiomerically pure bis-(1,2,3-triazolylmethyl)amino esters from modified α-amino acids.

Sarmiento-Sánchez Juan I JI Ochoa-Terán Adrián A Rivero Ignacio A IA

TheScientificWorldJournal 20141015

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 antio ...[more]

PMID: 25386592

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