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Molecules 2014, 19(6), 8051-8066; doi:10.3390/molecules19068051

A Class of Promising Acaricidal Tetrahydroisoquinoline Derivatives: Synthesis, Biological Evaluation and Structure-Activity Relationships

1
College of Science, Northwest A&F University, Yangling, Shaanxi 712100, China
2
College of Life Science, Northwest A&F University, Yangling, Shaanxi 712100, China
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Received: 1 April 2014 / Revised: 3 June 2014 / Accepted: 11 June 2014 / Published: 16 June 2014
(This article belongs to the Section Medicinal Chemistry)
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Abstract

As part of our continuing research on isoquinoline acaricidal drugs, this paper reports the preparation of a series of the 2-aryl-1-cyano-1,2,3,4-tetrahydroisoquinolines with various substituents on the N-phenyl ring, their in vitro acaricidal activities against Psoroptes cuniculi, a mange mite, and discusses their SAR as well. The structures of all compounds, including 12 new ones, were elucidated by analysis of UV, IR, NMR, ESI-MS, HR-MS spectra and X-ray diffraction experiments. All target compounds showed varying degrees of activity at 0.4 mg/mL. Compound 1 showed the strongest activity, with a 50% lethal concentration value (LC50) of 0.2421 μg/mL and 50% lethal time value (LT50) of 7.79 h, comparable to the standard drug ivermectin (LC50 = 0.2474 μg/mL; LT50 = 20.9 h). The SAR showed that the substitution pattern on the N-aromatic ring exerted a significant effect on the activity. The substituents 2'-F, 3'-F, 2'-Cl, 2'-Br and 2'-CF3 remarkably enhanced the activity. Generally, for the isomers with the same substituents at different positions, the order of the activity was ortho > meta > para. It was concluded that the target compounds represent a class of novel promising candidates or lead compounds for the development of new tetrahydroisoquinoline acaricidal agents. View Full-Text
Keywords: tetrahydroisoquinoline; acaricidal activity; Psoroptes cuniculi; structure-activity relationship tetrahydroisoquinoline; acaricidal activity; Psoroptes cuniculi; structure-activity relationship
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Yang, R.; Ruan, Q.; Zhang, B.-Y.; Zheng, Z.-L.; Miao, F.; Zhou, L.; Geng, H.-L. A Class of Promising Acaricidal Tetrahydroisoquinoline Derivatives: Synthesis, Biological Evaluation and Structure-Activity Relationships. Molecules 2014, 19, 8051-8066.

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