Bioactivity and structure–activity relationship of cinnamic acid derivatives and its heteroaromatic ring analogues as potential high-efficient acaricides against Psoroptes cuniculi

Chen, Dongdong; Zhang, Bingyu; Liu, Xiuxiu; Li, Xingqiang; Yang, Xin; Zhou, Le

doi:10.1016/j.bmcl.2017.08.051

Cited by 17 publications

(16 citation statements)

References 24 publications

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“…Compounds exhibiting higher activity were further studied for median lethal concentrations (LC 50 ) and median lethal times (LT 50 ) in comparison with the reference drug, ivermectin [52]. Based on Table 10, compounds 67-75 and 79 had a mean mortality of 84% and above with only compounds 77 and 78 exhibiting mean mortality below 40% at 0.5 mg/mL.…”

Section: Cinnamic Acid Derivatives With Antiparasitic Activitymentioning

confidence: 99%

“…Based on Table 10, compounds 67-75 and 79 had a mean mortality of 84% and above with only compounds 77 and 78 exhibiting mean mortality below 40% at 0.5 mg/mL. These compounds were potent when compared to ivermectin, an acaricidal agent due to factors such as lower molecular weight and simplified structure, affordability and non-toxicity to mammals and higher activity [52,53]. All the compounds displayed LC 50 values higher than ivermectin.…”

Section: Cinnamic Acid Derivatives With Antiparasitic Activitymentioning

confidence: 99%

“…Activity decreased when ester (68) was changed to thiol ester (79). Replacing the phenyl group (68) with 2-pyridinyl (71) or 2-furanyl (74) increased the activity [52]. Based on the different reports on the antiparasitic activity of cinnamic derivatives, the potent cinnamic acid derivatives with antimalarial activity are 36c, 36g, 36h and 37b [33].…”

Section: Ivermectinmentioning

confidence: 99%

“…The structure–activity relationship of the derivatives was studied. Compounds exhibiting higher activity were further studied for median lethal concentrations (LC 50 ) and median lethal times (LT 50 ) in comparison with the reference drug, ivermectin [ 52 ].…”

Section: Cinnamic Acid Derivatives With Antiparasitic Activitymentioning

confidence: 99%

“…Mean mortality percentages of Psoroptes cuniculi when incubated with 0.5 mg/mL and 0.25 mg/mL of different compounds[52].…”

mentioning

confidence: 99%

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Cinnamic Acid Derivatives and Their Biological Efficacy

Ruwizhi

Aderibigbe

2020

IJMS

253

134

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The role played by cinnamic acid derivatives in treating cancer, bacterial infections, diabetes and neurological disorders, among many, has been reported. Cinnamic acid is obtained from cinnamon bark. Its structure is composed of a benzene ring, an alkene double bond and an acrylic acid functional group making it possible to modify the aforementioned functionalities with a variety of compounds resulting in bioactive agents with enhanced efficacy. The nature of the substituents incorporated into cinnamic acid has been found to play a huge role in either enhancing or decreasing the biological efficacy of the synthesized cinnamic acid derivatives. Some of the derivatives have been reported to be more effective when compared to the standard drugs used to treat chronic or infectious diseases in vitro, thus making them very promising therapeutic agents. Compound 20 displayed potent anti-TB activity, compound 27 exhibited significant antibacterial activity on S. aureus strain of bacteria and compounds with potent antimalarial activity are 35a, 35g, 35i, 36i, and 36b. Furthermore, compounds 43d, 44o, 55g–55p, 59e, 59g displayed potent anticancer activity and compounds 86f–h were active against both hAChE and hBuChE. This review will expound on the recent advances on cinnamic acid derivatives and their biological efficacy.

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Section: Cinnamic Acid Derivatives With Antiparasitic Activitymentioning

confidence: 99%

Section: Cinnamic Acid Derivatives With Antiparasitic Activitymentioning

confidence: 99%

Section: Ivermectinmentioning

confidence: 99%

Section: Cinnamic Acid Derivatives With Antiparasitic Activitymentioning

confidence: 99%

“…Mean mortality percentages of Psoroptes cuniculi when incubated with 0.5 mg/mL and 0.25 mg/mL of different compounds[52].…”

mentioning

confidence: 99%

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Cinnamic Acid Derivatives and Their Biological Efficacy

Ruwizhi

Aderibigbe

2020

IJMS

253

134

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Synthesis and evaluation of novel xanthine‐acrylamides and xanthine‐acrylates as insecticidal agents

Zhang

Liu

Yang

et al. 2022

Pest Management Science

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BACKGROUND The design and discovery of novel pesticidal agents according to bioactive natural products is an important aspect of agrochemical innovation. New xanthine derivatives derived from natural xanthine or methylxanthines are rich resources that possess great potential to afford new active pesticidal molecules. Herein novel xanthine derivatives were designed through a strategy of combining the methylxanthine caffeine skeleton with the acrylamide or acrylate motif of cinnamic acid derivatives. RESULTS A series of novel (E)‐3‐(1,3,7‐trimethyl‐2,6‐dioxo‐2,3,6,7‐tetrahydro‐1H‐purin‐8‐yl)acrylic acid derivatives, caffeine‐(E)‐acrylamides and caffeine‐(E)‐acrylates, were synthesized and confirmed via melting points, 1H NMR, 13C NMR and high‐resolution mass spectrometry. A single crystal of compound I12 was obtained to illustrate the trans‐configuration of the vinyl double bond. Preliminary insecticidal evaluations showed that some of the compounds had favorable insecticidal potentials against Mythimna separata Walker at 200 mg L−1. Some of the compounds exhibited excellent insecticidal activity against Plutella xylostella L. at low test concentrations, e.g. I18 and I24 with LC50 values of 0.0435 and 0.0133 mg L−1, respectively, were found to be more potent than the insecticide control triflumuron. The structure–activity relationship (SAR) analysis is also given in detail. CONCLUSION Compounds I12, I18, I24 and I26 generated from the integration of natural methylxanthine (caffeine) and acrylate moieties could be novel insecticidal leading compounds for further structural optimization. The SAR analysis may bring a new inspiration to the extensive and deep investigations on new xanthine derivatives in the agrochemical area.

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