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. 2008 May 27;105(21):7359-64.
doi: 10.1073/pnas.0800571105. Epub 2008 May 27.

Synthesis and bioassay of improved mosquito repellents predicted from chemical structure

Alan R Katritzky  1 , Zuoquan Wang, Svetoslav Slavov, Maia Tsikolia, Dimitar Dobchev, Novruz G Akhmedov, C Dennis Hall, Ulrich R Bernier, Gary G Clark, Kenneth J Linthicum
Affiliations

Synthesis and bioassay of improved mosquito repellents predicted from chemical structure

Alan R Katritzky et al. Proc Natl Acad Sci U S A. .

Abstract

Mosquito repellency data on acylpiperidines derived from the U.S. Department of Agriculture archives were modeled by using molecular descriptors calculated by CODESSA PRO software. An artificial neural network model was developed for the correlation of these archival results and used to predict the repellent activity of novel compounds of similar structures. A series of 34 promising N-acylpiperidine mosquito repellent candidates (4a-4q') were synthesized by reactions of acylbenzotriazoles 2a-2p with piperidines 3a-3f. Compounds (4a-4q') were screened as topically applied mosquito repellents by measuring the duration of repellency after application to cloth patches worn on the arms of human volunteers. Some compounds that were evaluated repelled mosquitoes as much as three times longer than N,N-diethyl-m-toluamide (DEET), the most widely used repellent throughout the world. The newly measured durations of repellency were used to obtain a superior correlation equation relating mosquito repellency to molecular structure.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Fig. 1.
Fig. 1.
Synthetic scheme for the preparation of N-acylpiperidines 4. Bt, benzotriazolyl.
Fig. 2.
Fig. 2.
Histograms and probability density functions of the averaged protection time (PT) at 25 μmol/cm2 (a) and 2.5 μmol/cm2 (b).
Fig. 3.
Fig. 3.
Plot of R2 vs. number of descriptors used.
Fig. 4.
Fig. 4.
Predicted vs. observed protection time values at concentrations 25 and 2.5 μmol/cm2.
See this image and copyright information in PMC

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