Design and semisynthesis of new herbicide as 1,2,3-triazole derivatives of the natural maslinic acid

Steroids
Aymen Ben NejmaHichem Ben Jannet

Abstract

Interesting biological activities (anti-inflammatory, anticancer, antiviral, antioxidant, antidiabetic…) have been reported for maslinic acid (MA) and MA-based compounds. In continuation of our previous work on MA, herbicide potential of Tunisian plant extracts and 1,4-triazolyl derivatives of MA, we now wish to report semisynthesis of new MA-based triazole hybrid compounds with herbicide potential. These compounds were synthesized through Cu-catalyzed azide-alkyne cycloaddition (CuAAC) under microwave irradiation conditions between propargylated MA and a series of phthalimide azides. Here, the first partner of CuAAC reaction (propargylated MA) resulted from propargylation of C-28 carboxylic acid group of isolated MA from the well-known Mediterranean plant Olea europaea L. (Oleaceae). So far, phthalimide azide derivatives were achieved by trapping of N-acyliminium ion, in-situ generated under catalytic condition of Bi(OTf)3, by aromatic nucleophiles. The cycloaddition reaction afforded regiospecifically 1,4-disubstituted triazoles in good yields. The latter hybrid compounds were shown to exhibit a high inhibition potential of seed germination. This constitutes the first step in development of potent herbicides since one of the ...Continue Reading

References

Sep 22, 2006·The Journal of Nutrition·M Emília JuanJoana M Planas
Apr 2, 2013·Journal of Natural Products·Francisco R NietoJosé M Baeyens
Jan 7, 2014·Journal of Chemical Ecology·Chao-Min WangChang-Hung Chou
Feb 7, 2014·Critical Reviews in Food Science and Nutrition·Vildan Uylaşer, Gökçen Yildiz
Apr 13, 2015·Food Chemistry·Karim ChouaïbM'hamed Ali Hamza

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Citations

Mar 13, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Marissa TrujilloAllen Schoffstall
Jul 10, 2019·Chemistry : a European Journal·Samantha A OrrVictoria L Blair

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