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

摘要

According to our previous work and the latest research on the biosynthesis of beta-carboline, and using the reverse thinking strategy, tryptophan, the biosynthesis precursor of beta-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%, 500 mu g/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. (C) 2016 Published by Elsevier Ltd.