C ring may be dispensable for β-carboline: Design, synthesis, and bioactivities evaluation of tryptophan analog derivatives based on the biosynthesis of β-carboline alkaloids

Bioorganic & Medicinal Chemistry
Yuan-qiong HuangQingmin Wang

Abstract

According to our previous work and the latest research on the biosynthesis of β-carboline, and using the reverse thinking strategy, tryptophan, the biosynthesis precursor of β-carboline alkaloids, and their derivatives were synthesized, and their biological activities and structure-activity relationships were studied. This bioassay showed that these compounds exhibited good inhibitory activities against tobacco mosaic virus (TMV); especially (S)-2-amino-3-(1H-indol-3-yl)-N-octylpropanamide (4) (63.3±2.1%, 67.1±1.9%, 68.7±1.3%, and 64.5±3.1%, 500μg/mL) exhibited the best antiviral activity both in vitro and in vivo. Compound 4 was chosen for the field trials and the acute oral toxicity test, the results showed that the compound exhibited good anti-TMV activity in the field and low acute oral toxicity. We also found that these compounds showed antifungal activities and insecticidal activities.

Citations

Oct 30, 2016·European Journal of Medicinal Chemistry·Valéria Aquilino BarbosaMaria Helena Sarragiotto
Mar 19, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Katharigatta N VenugopalaViresh Mohanlall
Jun 6, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xin-Yu HuoBin Dai

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