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, a...
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| Format: | Article |
| Language: | English |
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Wiley
2014-01-01
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| Series: | The Scientific World Journal |
| Online Access: | http://dx.doi.org/10.1155/2014/264762 |
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| author | Juan I. Sarmiento-Sánchez Adrián Ochoa-Terán Ignacio A. Rivero |
| author_facet | Juan I. Sarmiento-Sánchez Adrián Ochoa-Terán Ignacio A. Rivero |
| author_sort | Juan I. Sarmiento-Sánchez |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-e3a8bb47f4184f08a60d2922ee31ac43 |
| institution | Kabale University |
| issn | 2356-6140 1537-744X |
| language | English |
| publishDate | 2014-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | The Scientific World Journal |
| spelling | doaj-art-e3a8bb47f4184f08a60d2922ee31ac432025-02-03T01:27:53ZengWileyThe Scientific World Journal2356-61401537-744X2014-01-01201410.1155/2014/264762264762Synthesis and Antioxidant Evaluation of Enantiomerically Pure Bis-(1,2,3-triazolylmethyl)amino Esters from Modified α-Amino AcidsJuan I. Sarmiento-Sánchez0Adrián Ochoa-Terán1Ignacio A. Rivero2Facultad de Ingeniería, Universidad Autónoma de Sinaloa, Boulevard de las Américas S/N, 80040 Culiacán, SIN, MexicoCentro de Graduados e Investigación del Instituto Tecnológico de Tijuana, Boulevard Alberto Limón Padilla S/N, Apdo. Postal 1166, 22500 Tijuana, BC, MexicoCentro de Graduados e Investigación del Instituto Tecnológico de Tijuana, Boulevard Alberto Limón Padilla S/N, Apdo. Postal 1166, 22500 Tijuana, BC, MexicoThe 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.http://dx.doi.org/10.1155/2014/264762 |
| spellingShingle | Juan I. Sarmiento-Sánchez Adrián Ochoa-Terán Ignacio A. Rivero Synthesis and Antioxidant Evaluation of Enantiomerically Pure Bis-(1,2,3-triazolylmethyl)amino Esters from Modified α-Amino Acids The Scientific World Journal |
| title | Synthesis and Antioxidant Evaluation of Enantiomerically Pure Bis-(1,2,3-triazolylmethyl)amino Esters from Modified α-Amino Acids |
| title_full | Synthesis and Antioxidant Evaluation of Enantiomerically Pure Bis-(1,2,3-triazolylmethyl)amino Esters from Modified α-Amino Acids |
| title_fullStr | Synthesis and Antioxidant Evaluation of Enantiomerically Pure Bis-(1,2,3-triazolylmethyl)amino Esters from Modified α-Amino Acids |
| title_full_unstemmed | Synthesis and Antioxidant Evaluation of Enantiomerically Pure Bis-(1,2,3-triazolylmethyl)amino Esters from Modified α-Amino Acids |
| title_short | Synthesis and Antioxidant Evaluation of Enantiomerically Pure Bis-(1,2,3-triazolylmethyl)amino Esters from Modified α-Amino Acids |
| title_sort | synthesis and antioxidant evaluation of enantiomerically pure bis 1 2 3 triazolylmethyl amino esters from modified α amino acids |
| url | http://dx.doi.org/10.1155/2014/264762 |
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