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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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Mentions: Click chemistry has been defined as an efficient and an almost perfect method (very selective, with high yields and wide scope) for the synthesis of new and diverse compounds based in a carbon-heteroatom bond formation. This reaction has been particularly useful for coupling two molecules, azides and alkynes, to get 1,2,3-triazole compounds [1]. However, it was only after the discovery of copper catalysis that its applications began to be studied [2]. Click chemistry meets the requirements of an innovative functionalization strategy for biomolecules because it is efficient, selective, and without side reactions. Rostovtsev et al. [3] and Tornøe et al. [4] have reported that 1,4-disubstituted 1,2,3-triazoles are specifically prepared from azides and terminal alkynes under copper(I) catalysis to give 1,4-substituted products with high regioselectivity. The regioisomeric 1,5-disubstituted triazoles are available from azides and terminal alkynes by the use of either magnesium acetylides or ruthenium catalysts [1, 5, 6]. 1,2,3-Triazole compounds have attracted attention because they exhibit a broad variety of biological activities. For example, compounds such as 1 are active against Mycobacterium tuberculosis [7]; other compounds act as anticancer 2 [8], antifungal 3 [9], or antitumor agents 4 [10], Scheme 1. Some biomedical applications have been described, for example, the labelling of biomolecules [11]. In addition, 1,2,3-triazoles have been used in the coupling of modified α-amino acids in oligopeptide synthesis [4, 12–17]. Furthermore, this class of modified oligopeptides 5 showed activity as inhibitors of cysteine protease CPB2.8ΔCTE in Leishmania mexicana [18] and antiviral activity against HIV-1 gp120 [19, 20].


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)

© Copyright Policy - open-access
Related In: Results  -  Collection

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

Mentions: Click chemistry has been defined as an efficient and an almost perfect method (very selective, with high yields and wide scope) for the synthesis of new and diverse compounds based in a carbon-heteroatom bond formation. This reaction has been particularly useful for coupling two molecules, azides and alkynes, to get 1,2,3-triazole compounds [1]. However, it was only after the discovery of copper catalysis that its applications began to be studied [2]. Click chemistry meets the requirements of an innovative functionalization strategy for biomolecules because it is efficient, selective, and without side reactions. Rostovtsev et al. [3] and Tornøe et al. [4] have reported that 1,4-disubstituted 1,2,3-triazoles are specifically prepared from azides and terminal alkynes under copper(I) catalysis to give 1,4-substituted products with high regioselectivity. The regioisomeric 1,5-disubstituted triazoles are available from azides and terminal alkynes by the use of either magnesium acetylides or ruthenium catalysts [1, 5, 6]. 1,2,3-Triazole compounds have attracted attention because they exhibit a broad variety of biological activities. For example, compounds such as 1 are active against Mycobacterium tuberculosis [7]; other compounds act as anticancer 2 [8], antifungal 3 [9], or antitumor agents 4 [10], Scheme 1. Some biomedical applications have been described, for example, the labelling of biomolecules [11]. In addition, 1,2,3-triazoles have been used in the coupling of modified α-amino acids in oligopeptide synthesis [4, 12–17]. Furthermore, this class of modified oligopeptides 5 showed activity as inhibitors of cysteine protease CPB2.8ΔCTE in Leishmania mexicana [18] and antiviral activity against HIV-1 gp120 [19, 20].

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