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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 JI, Ochoa-Terán A, Rivero IA - ScientificWorldJournal (2014)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Facultad de Ingeniería, Universidad Autónoma de Sinaloa, Boulevard de las Américas S/N, 80040 Culiacán, SIN, Mexico.

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 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.

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Synthesis of bis-(1,2,3-triazolyl) compounds using modified α-amino acids.
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sch3: Synthesis of bis-(1,2,3-triazolyl) compounds using modified α-amino acids.

Mentions: Recently, we have reported the synthesis of new enantiomerically pure compounds from chemical modifications of α-amino acids [43–45]. Continuing our research interest in triazoles chemistry [46, 47], now we report our efforts in the synthesis of new enantiopure 1,4-disubstituted 1,2,3-triazoles via conventional Huisgen cycloaddition using α-halomethyl ketones 10 and α-N,N-dipropargylamino esters 11 as one strategy for coupling in solution two enantiopure moieties derived from α-amino acids. From a combinatorial chemistry approach, the methodology developed in the present work could allow preparing a library of analogues, depending on the number and nature of α-amino acids synthetically modified. It is then feasible to expect a different behavior for each one of the possible products. We envisioned potential for these new bis-(1,2,3-triazolylmethyl)amino esters 6 (Scheme 3) as biologically active substances and as building blocks for the syntheses of interesting modified oligopeptides.


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

Sarmiento-Sánchez JI, Ochoa-Terán A, Rivero IA - ScientificWorldJournal (2014)

Synthesis of bis-(1,2,3-triazolyl) compounds using modified α-amino acids.
© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4216715&req=5

sch3: Synthesis of bis-(1,2,3-triazolyl) compounds using modified α-amino acids.
Mentions: Recently, we have reported the synthesis of new enantiomerically pure compounds from chemical modifications of α-amino acids [43–45]. Continuing our research interest in triazoles chemistry [46, 47], now we report our efforts in the synthesis of new enantiopure 1,4-disubstituted 1,2,3-triazoles via conventional Huisgen cycloaddition using α-halomethyl ketones 10 and α-N,N-dipropargylamino esters 11 as one strategy for coupling in solution two enantiopure moieties derived from α-amino acids. From a combinatorial chemistry approach, the methodology developed in the present work could allow preparing a library of analogues, depending on the number and nature of α-amino acids synthetically modified. It is then feasible to expect a different behavior for each one of the possible products. We envisioned potential for these new bis-(1,2,3-triazolylmethyl)amino esters 6 (Scheme 3) as biologically active substances and as building blocks for the syntheses of interesting modified oligopeptides.

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Facultad de Ingeniería, Universidad Autónoma de Sinaloa, Boulevard de las Américas S/N, 80040 Culiacán, SIN, Mexico.

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 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.

Show MeSH