Synthesis, bioactivity and mode of action of 5A5B6C tricyclic spirolactones as novel antiviral lead compounds

Zhu, Yu‐Jie; Wu, Qifan; Fan, Zhijin; Huo, Jingqian; Zhang, Jinlin; Zhao, Bin; Chen, Lai; Qian, Xiaolin; Ma, Dejun; Wang, Dawei

doi:10.1002/ps.5115

Cited by 24 publications

(17 citation statements)

References 51 publications

(82 reference statements)

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“…The anti‐TMV activty of the target compounds was evaluated through inactive, protective, curative and inductive models with three replicates by our previous reported methods 31 . Ribavirin, ningnanmycin, TDL and isotianil were used as corresponding positive controls.…”

Section: Methodsmentioning

confidence: 99%

“…The anti-TMV activty of the target compounds was evaluated through inactive, protective, curative and inductive models with three replicates by our previous reported methods. 31 Ribavirin, ningnanmycin, TDL and isotianil were used as corresponding positive controls. Target compounds and controls were dissolved in N,N-dimethyl formamide (DMF) and diluted with water (containing 0.1% Tween 80) to obtain the test concentration of 100 μg mL -1 .…”

Section: Anti-tmv Activitymentioning

confidence: 99%

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Synthesis of novel N‐(2‐phenyl‐3‐pyridyl) thiadiazole/isothiazole carboxamide analogs as potent plant elicitors

Yang

Калинина

et al. 2021

Pest Management Science

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BACKGROUND: Plant elicitors are a class of plant protection agents that can stimulate plant immunity against phytopathogen without a potential resistance problem. In searching for novel plant elicitor candidates, a series of novel N-(2-phenyl-3-pyridyl) thiadiazole/isothiazole carboxamide analogs were designed and synthesized. RESULTS:In vitro bioassay showed that all new compounds exhibited weak direct fungicidal activity. However, compounds 3b, 3g, 3n and 3o showed broad spectrum of in vivo activity against four plant fungi tested. In particularly, 3g showed 80% activity against Rhizoctonia solani in a glasshouse at a concentration of 1 ∼g mL -1 . For induction activity of tobacco against tobacco mosaic virus (TMV), compounds 3c and 3v showed 67% and 68% inhibitory activity, respectively, which were superior to the positive controls ribavirin and ningnanmycin. Compound 3g showed moderate induction activity (41%). Reverse transcription quantitative polymerase chain reaction (RT-qPCR) analysis found that, 3g could up-regulate expression of genes that are related to reactive oxygen species (ROS), pathogenesis-related protein (PRP) and salicylic acid (SA) signalling.CONCLUSION: These results indicated that 3g as an elicitor candidate might act on the SA signalling pathway. According to our findings, N-(2-phenyl-3-pyridyl) thiadiazole/isothiazole carboxamide analogs might be promising lead scaffolds as a novel plant elicitor for further investigation.

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Section: Methodsmentioning

confidence: 99%

Section: Anti-tmv Activitymentioning

confidence: 99%

Synthesis of novel N‐(2‐phenyl‐3‐pyridyl) thiadiazole/isothiazole carboxamide analogs as potent plant elicitors

Yang

Калинина

et al. 2021

Pest Management Science

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“…For example, some antiviral tricyclic spirolactones have been reported to be able to cause TMV inactivation by inducing protein crosslinking and further reducing the efficiency of TMV uncoating. 26 In summary, we have accomplished a concise synthetic approach to all four diastereoisomers of the proposed structure of (±)-nicotlactone A [(±)-1] in only 5-6 steps from methyl acrylate. The 8'-hydroxy group next to the lactone ketone in the title products was introduced by a Mukaiyama-type hydration reaction.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Synthesis and Structure–Activity Relationship Studies of Nicotlactone Analogues as Anti-TMV Agents

He¹,

Chi²,

Chen³

et al. 2022

Synthesis

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The synthesis of the originally proposed structure of (±)-nicotlactone A, a potent antiviral lignan with three continuous chiral centers, is reported here in 5 steps from methyl acrylate. The key steps of the synthesis included an In-catalyzed regioselective allylation and a Mn-catalyzed Mukaiyama hydration reaction. Our synthetic strategy also enables us to get the other three epimers and investigate the structure-activity relationship. The NMR data of the synthesized compounds do not match that of the isolated sample, indicating that the structure of nicotlactone A remains to be reassigned. All the synthetic target compounds were evaluated for their anti-tobacco mosaic virus (anti-TMV) activity. Bioassay results indicated that (±)-8-demethylnicotlactone A displayed similar anti-TMV activity to the commercial agent ningnanmycin, thus being a promising candidate or lead compound for developing novel antiviral agents in crop protection.

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“…Tests with a mortality rate of less than 10% in the control group are effective tests. 18 1d-instar late larvae were selected from healthy Italian bee colonies, placed on a 48-well plate, and fed the same amount of basal diet (50% fresh royal jelly and 50% yeast extract containing 1%, 6% glucose and 6% fructose aqueous solution). After 3 days of adaptive rearing (temperature 34-35°C, humidity 95%), on the 4th day after the start of the test they were assigned to each treatment group.…”

Section: Toxicity Test To Italian Beesmentioning

confidence: 99%

Synthesis and biological activity of novel Pyrazolo[3,4‐d]pyrimidin‐4‐one derivatives as potent antifungal agent

Wang

Cheng

Cui

et al. 2021

Pest Management Science

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BACKGROUND: To promote the discovery and development of new fungicide with novel scaffolds or modes of action, a series of novel 5-(2-chloroethyl)-1-phenyl-6-(pyridin-4-yl)-1,5-dihydro-4H-pyrazolo [3,4-d]pyrimidin-4-one derivatives were synthesized, and evaluated for their antifungal activities.RESULTS: The bioassay data showed that compound 8IIId (EC 50 = 1.93 mg L −1 ) is superior to boscalid (EC 50 = 6.71 mg L −1 ) against Valsa mali. We introduced chiral groups on the structure of 8IIId, and two chiral configurations were respectively synthesized, which are 8Vc and 8Vd. Surprisingly, 8Vc showed significant antifungal activities against Valsa mali and Physalospora piricola with EC 50 values of 0.22 and 0.55 mg L −1 . Physiological and biochemical studies showed that the primary action mechanism of compound 8Vc on Valsa mali may involve changing mycelial morphology and increasing cell membrane permeability.CONCLUSION: These results demonstrated that 8Vc could be further modified as fungicide and provided a valuable reference for antifungal agents with pyrazolo [3,4-d]pyrimidin-4-one skeleton.

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Synthesis, bioactivity and mode of action of 5_A5_B6_C tricyclic spirolactones as novel antiviral lead compounds

Cited by 24 publications

References 51 publications

Synthesis of novel N‐(2‐phenyl‐3‐pyridyl) thiadiazole/isothiazole carboxamide analogs as potent plant elicitors

Synthesis of novel N‐(2‐phenyl‐3‐pyridyl) thiadiazole/isothiazole carboxamide analogs as potent plant elicitors

Synthesis and Structure–Activity Relationship Studies of Nicotlactone Analogues as Anti-TMV Agents

Synthesis and biological activity of novel Pyrazolo[3,4‐d]pyrimidin‐4‐one derivatives as potent antifungal agent

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Synthesis, bioactivity and mode of action of 5A5B6C tricyclic spirolactones as novel antiviral lead compounds

Cited by 24 publications

References 51 publications

Synthesis of novel N‐(2‐phenyl‐3‐pyridyl) thiadiazole/isothiazole carboxamide analogs as potent plant elicitors

Synthesis of novel N‐(2‐phenyl‐3‐pyridyl) thiadiazole/isothiazole carboxamide analogs as potent plant elicitors

Synthesis and Structure–Activity Relationship Studies of Nicot­lactone Analogues as Anti-TMV Agents

Synthesis and biological activity of novel Pyrazolo[3,4‐d]pyrimidin‐4‐one derivatives as potent antifungal agent

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Product

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Synthesis, bioactivity and mode of action of 5_A5_B6_C tricyclic spirolactones as novel antiviral lead compounds

Synthesis and Structure–Activity Relationship Studies of Nicotlactone Analogues as Anti-TMV Agents