Synthesis and Antimicrobial Characterization of Half-Calycanthaceous Alkaloid Derivatives.
A total of 29 novel tetrahydropyrroloindol-based calycanthaceous alkaloid derivatives were synthesized from indole-3-acetonitrile in good yields. The synthesized compounds were evaluated against nine strains of bacteria and a wide range of plant pathogen fungi. Bioassay results revealed that majority of the compounds displayed similar or higher in vitro antimicrobial activities than the positive control. The biological activities also indicated that substituents at R₄ and R₅ significantly affect the activities. Notably, compound c4 was found to be most active among the tested calycanthaceous analogues and might be a novel potential leading compound for further development as an antifungal agent. The results could pave the way for further design and structural modification of calycanthaceous alkaloids as antimicrobial agents.
School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, Jiangsu, China. sz281cam@just.edu.cn.|Key Laboratory of Protection & Utilization of Biological Resources in Tarim Basin of Xinjiang Production and Construction Corps/College of Life Sciences, Tarim University, Alar 843300, Xinjiang, China. sz281cam@just.edu.cn.|Key Laboratory of Botanical Pesticide R & D in Shaanxi Province, Yangling 712100, Shaanxi, China. sz281cam@just.edu.cn.
Shaojun
S
Zheng
Key Laboratory of Protection & Utilization of Biological Resources in Tarim Basin of Xinjiang Production and Construction Corps/College of Life Sciences, Tarim University, Alar 843300, Xinjiang, China. zhouzhouxinping@163.com.
Xinping
X
Zhou
Key Laboratory of Protection & Utilization of Biological Resources in Tarim Basin of Xinjiang Production and Construction Corps/College of Life Sciences, Tarim University, Alar 843300, Xinjiang, China. xsx_89@163.com.
Shixun
S
Xu
School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, Jiangsu, China. zhurui991314@163.com.
Rui
R
Zhu
Key Laboratory of Protection & Utilization of Biological Resources in Tarim Basin of Xinjiang Production and Construction Corps/College of Life Sciences, Tarim University, Alar 843300, Xinjiang, China. bhj67@163.com.
Hongjin
H
Bai
Key Laboratory of Protection & Utilization of Biological Resources in Tarim Basin of Xinjiang Production and Construction Corps/College of Life Sciences, Tarim University, Alar 843300, Xinjiang, China. nwzjw@nwsuaf.edu.cn.|Key Laboratory of Botanical Pesticide R & D in Shaanxi Province, Yangling 712100, Shaanxi, China. nwzjw@nwsuaf.edu.cn.
Jiwen
J
Zhang
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000254:growth & development*; D005670:Fusarium / Q000254:growth & development*
D000470:Alkaloids; D000890:Anti-Infective Agents
SAR; agrochemicals; biological activity; calycanthaceous alkaloids; synthesis