Abstract
A series of 3-aryl propionic esters and their analogues were designed and evaluated for acaricidal activity in vitro against Psoroptes cuniculi, a mange mite. The structure–activity relationship (SAR) was also discussed. The results showed that 6 compounds possessed the excellent activity (LC50 = 0.17–0.24 mM, LT50 = 1.5–2.9 h), superior to ivermectin (LC50 = 0.28 mM, LT50 = 8.9 h) (P < 0.05), a standard drug. Furthermore, 7 compounds showed the good activity (LC50 = 0.25–0.37 mM, LT50 < 3.9 h), slightly lower or close to that of ivermectin. One compound displayed super-fast acaricidal property, far superior to ivermectin. SAR analysis found that the ester group is vital for the activity and the small steric hindrance adjacent to the ester group is advantageous for the high activity. The <C4 linear alcohol esters can give the higher activity. The substituents on the 3-phenyl ring or replacement of the 3-phenyl with heterocyclic aryl generally decreases the activity. The position of the ester group in the ester chain also influences the activity, where the 3-phenyl propionate and the benzoate had the highest and lowest activity, respectively. Thus, 3-arylpropionates emerged as new and promising high-efficient acaricide candidates.
Highlights
Therapy and control of both human scabies and animal mange mainly depend on the use of drugs and chemicals[4]
In order to explore structure-activity relationship (SAR) and find more potent compounds, based on the principle of structural similarity and the consideration of molecular diversity, four series of the target compounds were designed by using ethyl 3-phenylpropinate (2) as a lead compound
The first series is a group of 3-phenylpropionic acid esters (1–31) derived from various alcohols or phenols to explore the effect of various alkyl groups of the alcoholic moiety on the activity
Summary
Dongdong Chen[1], Ye Tian[1,3], Mingxuan Xu1, Xinyuan Wang[2], Ding Li1, Fang Miao[2], Xinjuan Yang1 & Le Zhou[1]. A series of 3-aryl propionic esters and their analogues were designed and evaluated for acaricidal activity in vitro against Psoroptes cuniculi, a mange mite. The results showed that 6 compounds possessed the excellent activity (LC50 = 0.17– 0.24 mM, LT50 = 1.5–2.9 h), superior to ivermectin (LC50 = 0.28 mM, LT50 = 8.9 h) (P < 0.05), a standard drug. Interesting for us is that as the derivate of ethyl cinnamate, ethyl 3-phenylpropanoate showed greater acaricidal potential than ethyl cinnamate[25] This result strongly suggests that it is necessary to take a systematical investigate on acaricidal activity of 3-phenylpropanoic acid esters in order to discover more potent acaricidal agents. A series of 3-aryl propionic acid esters and their analogues were reported for design, syntheses, acaricidal activity against P. cuniculi and preliminary structure-activity relationship (SAR)
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