Synthesis and Antioxidant Evaluation of Enantiomerically Pure Bis-(1,2,3-triazolylmethyl)amino Esters from Modifiedα-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 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.

ZnO Nanoparticles: Efficient and Versatile Reagents for Synthesis of 1,4-disubstituted 1,2,3-triazoles

“…1 H, 13 C NMR and IR spectroscopy and elemental analyses. 20,29,[33][34][35][36][37] Compound 3q was known and our IR and 1 H NMR spectroscopic data of compound is in agreement with previously reported spectral data. 29 Compounds 3r-u were new and their structures were deduced by elemental and spectral analysis.…”

Tandem synthesis of 1-formyl-1,2,3-triazoles

“…The direct synthesis from propynal has been reported, 32 but is impractical due to this reagent’s low boiling point and lack of commercial availability. A two-step method of CuAAC reaction with propargyl alcohol followed by oxidation of the hydroxymethylated triazole intermediate with reagents such as CrO 3 24 or MnO 2 30 is effective but limited to substituents that can withstand such oxidants, and is environmentally unfriendly.…”

O‐(Triazolyl)methyl Carbamates as a Novel and Potent Class of Fatty Acid Amide Hydrolase (FAAH) Inhibitors

“…Then, copper catalyzed [3 + 2] cycloaddition reaction between azides 5a and 5b with the commercially available but-3-yn-1-ol, allowed us to obtain compounds 31a and 31b in acceptable yields. [24] Finally, compounds 32 and 33 were prepared by coupling alcohols 31a and 31b , respectively, with commercial cyclohexyl isocyanate (Scheme 2). …”