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

[Display omitted] 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...

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Published in:Bioorganic & medicinal chemistry 2016-02, Vol.24 (3), p.462-473
Main Authors: Huang, Yuanqiong, Liu, Yongxian, Liu, Yuxiu, Song, Hongjian, Wang, Qingmin
Format: Article
Language:English
Subjects:
Animals
Anti-TMV
Antiviral Agents - chemistry
Antiviral Agents - metabolism
Antiviral Agents - pharmacology
Biosynthesis
Carbolines - chemistry
Carbolines - metabolism
Carbolines - pharmacology
Culex - drug effects
Dose-Response Relationship, Drug
Drug Design
Fungi - drug effects
Fungicide
Fungicides, Industrial - metabolism
Fungicides, Industrial - pharmacology
Insecticides - chemistry
Insecticides - metabolism
Insecticides - pharmacology
Microbial Sensitivity Tests
Molecular Structure
Rats
Structure-Activity Relationship
Tobacco mosaic virus
Tobacco Mosaic Virus - drug effects
Tryptophan
Tryptophan - analogs & derivatives
β-Carboline
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Summary:[Display omitted] 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.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2015.08.016