Retraction of Novel acetylcholinesterase inhibitors: Synthesis and activity of phthalimide alkyloxylphenyl N,N-dimethylcarbamate derivatives

Zhao, Qilong; Yang, Guoquan; Mei, Xiangdong; Yuan, Huizhu; Ning, Jun

doi:10.1584/jpestics.g09-07

Cited by 2 publications

(4 citation statements)

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“…The data in Table show that all N , N -dimethylcarbamate heterodimetic derivatives exhibited the same low inhibition of AChE as parent phenyl N , N -dimethylcarbamate (IC 50 = 2961 μg mL −1 ) , whereas N -methylcarbamate heterodimeric molecules showed higher inhibition against AChE than N , N -dimethylcarbamate heterodimetic molecules. The AChE inhibition potency of the carbamate heterodimetic derivatives varied evidently with the length of the tether chain.…”

Section: Resultsmentioning

confidence: 95%

“…AChE was prepared from heads of adult houseflies (female/ male = 1:1). Inhibitory activities of these compounds were measured against AChE according to a previously reported method , .…”

Section: Methodsmentioning

confidence: 99%

“…Continuing with our research on dual-site inhibitors of AChE in the pesticide field , and hypothesizing that the phenoxy moiety would be able to interact with aromatic amino acid residues through π−π interactions, we have designed and synthesized a series of novel carbamate derivatives incorporated with a phenoxy moiety as potential AChE inhibitors to enhance the insecticidal activity and to overcome the resistance via additional interaction in the gorge of the AChE.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Insecticidal Activity of Novel Carbamate Derivatives as Potential Dual-Binding Site Acetylcholinesterase Inhibitors

Xie

Zhao

et al. 2010

J. Agric. Food Chem.

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In biological systems, bivalent ligands often possess increased functional affinity for their receptors compared with monovalent ligands. On the basis of the structure of acetylcholinesterase (AChE), a series of novel carbamate heterodimetic derivatives were designed and synthesized with the aim of increasing the potency toward AChE inhibition. The AChE inhibitory ability of all the novel compounds was tested using AChE obtained from the brain of the housefly. The bioassay results showed that compounds 6j, 6k, 6m, 6n, 6p, and 6q had increased inhibitory activities in comparison with parent phenyl N-methylcarbamate (MH) at the concentration of 100 mg/L. Among them, the most potent AChE inhibitor of these compounds was 6q (IC(50) = 12 μM), which showed 62-fold greater AChE inhibitory activity than that of MH and 12-fold greater activity than metolcarb (MT), which suggested that the 3-nitrophenoxy moiety of compound 6q was able to interact with the aromatic amino acid residues lining the gorge and the phenyl N-methylcarbamate moiety was able to interact with the catalytic sites of AChE, simultaneously. The insecticidal activities of compounds 6j, 6k, 6m, 6n, 6p, and 6q were further evaluated. Consistent with the result in vitro bioassay, those compounds demonstrated better activities against Lipaphis erysimi than parent compound MH at the concentration of 300 mg/L, and compound 6q showed the best insecticidal activity, causing 98% mortality after 24 h of treatment.

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Section: Resultsmentioning

confidence: 95%

“…AChE was prepared from heads of adult houseflies (female/ male = 1:1). Inhibitory activities of these compounds were measured against AChE according to a previously reported method , .…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Insecticidal Activity of Novel Carbamate Derivatives as Potential Dual-Binding Site Acetylcholinesterase Inhibitors

Xie

Zhao

et al. 2010

J. Agric. Food Chem.

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“…Based on the multiple binding sites of acetylcholinesterase (AChE), a series of AChE inhibitors involving phthalimide derivatives have been designed and synthesized, see: Zhao et al (2009). Phthalimide derivatives have also been developed as LXRa-selective antagonists, see: Motoshima et al (2009).…”

Section: Related Literaturementioning

confidence: 99%