Abstract
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.
Highlights
As a part of conventional agriculture, agrochemicals play an important role in the protection of vegetable and cereal crops
North America and Australia [7,8], are an important class of alkaloids that can be isolated from the roots, leaves, flowers, and fruits of Chimonanthus praecox [9], and have demonstrated widespread biological activities such as anticonvulsant, antifungal, antiviral, analgesic, antitumor, and inhibition of melanogenesis properties [10–13]
It was hoped that a leading compound could be identified for the discovery of novel antimicrobial agents
Summary
As a part of conventional agriculture, agrochemicals play an important role in the protection of vegetable and cereal crops. To reduce the negative impacts of agrochemicals, new compounds with high efficacy against target species are desired. North America and Australia [7,8], are an important class of alkaloids that can be isolated from the roots, leaves, flowers, and fruits of Chimonanthus praecox [9], and have demonstrated widespread biological activities such as anticonvulsant, antifungal, antiviral, analgesic, antitumor, and inhibition of melanogenesis properties [10–13]. Due to their broad spectrum of biological properties, a number of studies towards the synthesis and antimicrobial activity of calycanthaceous alkaloids have been reported [13–25]. A series of novel calycanthaceous alkaloids analogs were designed and synthesized using indole-3-acetonitrile as the starting material
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