Synthesis of Triazole Derivatives of Levoglucosenone As Promising Anticancer Agents: Effective Exploration of the Chemical Space through retro-aza-Michael//aza-Michael Isomerizations

Abstract

The design and synthesis of biomass-derived triazoles and the in vitro evaluation as potential anticancer agents are described. The discovery of base-catalyzed retro-aza-Michael//aza-Michael isomerizations allowed the exploration of the chemical space by affording novel types of triazoles, difficult to obtain otherwise. Following this strategy, 2,4-disubstituted 1,2,3-triazoles could be efficiently obtained from the corresponding 1,4-disubstituted analogues.

Cycloamination strategies for renewable N-heterocycles

“…For example, in the absence of any chiral catalyst, cellulose-derived (−)-levoglucosenone can undergo well-controlled reactions like 1,3-dipolar cycloaddition, aza-Michael addition or isomerization, being enantioselectively converted into polysub-stituted pyrrolidines or 1,2,3-triazoles. [327][328][329] A versatile protocol via multicomponent Ugi-type reactions of unprotected saccharides and L-or D-configured amino acids is accessible to 1,2-syn or anti configured products, respectively. 330 In this regard, the exploitation of synthetic protocols to biomassderived chiral molecules, especially those with potent bioactivities, is promising with respect to green manufacturing processes.…”

Synthesis of Nerol Derivatives Containing a 1,2,3-Triazole Moiety and Evaluation of Their Activities against Cancer Cell Lines

“…Compound 9f was obtained as a yellow oil in 41% yield (127 mg, 0.310 mmol) from 4-trifluoromethoxybenzylazide (3f) (163 mg, 0.750 mmol) and compound 7 (144.0 mg, 0.750 mmol). TLC: Rf = 0.28 (hexane/ethyl acetate/ dichloromethane 3:1: 9, 327 7, 274 (27), 257 52…”

“…In this transformation, a 1,2,3-triazole ring 1,4-disubstituted is obtained from a terminal alkyne and an azide and it is commonly known in the literature as click reaction. A variety of bioactive compounds, 21 including anticancer agents, [22][23][24][25][26][27] have been synthesized using the click reaction as the key step. It should be mentioned that 1,2,3-triazole ring is an attractive unit, since it is stable to metabolic degradation, oxidative/reducing conditions, and improves solubility by actively binding to biomolecular targets.…”

“…3), 286(6), 273(1), 220 (3), 203(4), 134 (3), 121 (100), 107 (3), 91(12), 77(17), 69(27), 53(10),41 (60). (Z)-4-(((3,7-Dimethylocta-2,6-dien-1-yl)oxy)methyl)-1-(4-nitrobenzyl)-1H-1,2,3-triazole (9i) Compound 9i was obtained as a yellow oil in 40% yield (96.0 mg, 0.260 mmol) from 4-nitrobenzylazide (3i) (134 mg, 0.750 mmol) and compound 7 (144 mg, 0.750 mmol).…”

Synthesis, antibacterial, and antioxidant activities of naphthyl‐linked disubstituted 1,2,3‐triazoles

“…In recent years, chemical and biological usefulness of heterocyclic compounds attracted attention of chemist in form of pharmaceuticals, agrochemicals, polymers, dyes, etc . Triazole, a five‐membered heterocycle is key important, as its derivatives exhibited various biological activities such as antibacterial, antimalarial, antitubercular, anticancer, antiparasitic, antileishmanial, antioxidant, anti‐inflammatory, antidepressant, antiviral, etc. The 1,2,3‐triazole derivatives play an intriguing role in the development of new drugs, as effectively exerts various non‐covalent interactions which improves the solubility and the ability of binding to bimolecular targets …”