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.
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.
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China.
Yuanqiong
Y
Huang
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China.
Yongxian
Y
Liu
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China.
Yuxiu
Y
Liu
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China.
Hongjian
H
Song
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China. Electronic address: wangqm@nankai.edu.cn.
Qingmin
Q
Wang
D000818:Animals; D000998:Antiviral Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D002243:Carbolines / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D003465:Culex / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D005658:Fungi / Q000187:drug effects; D005659:Fungicides, Industrial / Q000378:metabolism / Q000494:pharmacology*; D007306:Insecticides / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D051381:Rats; D013329:Structure-Activity Relationship; D014027:Tobacco Mosaic Virus / Q000187:drug effects; D014364:Tryptophan / Q000031:analogs & derivatives*
D000998:Antiviral Agents; D002243:Carbolines; D005659:Fungicides, Industrial; D007306:Insecticides; D014364:Tryptophan; C010262:norharman
Anti-TMV; Biosynthesis; Fungicide; Tryptophan; β-Carboline