Three dimensional structure-activity relationships (3D-QSAR) for insect repellency of diastereoisomeric compounds: A hierarchical molecular overlay approach

SAR and QSAR in Environmental Research

Volumn 18, Issue 3-4, 2007, Pages 237-250

  Basak, S C ^a   Natarajan, R ^b   Nowak, W ^b   Miszta, P ^b   Klun, J A ^c  

^a UNIVERSITY OF MINNESOTA DULUTH   (United States)

^b NICOLAUS COPERNICUS UNIVERSITY   (Poland)

^c AGRICULTURAL RESEARCH SERVICE   (United States)

Author keywords

3 D QSAR; Ab initio calculations; AI3 37220; Mosquito repellents; Overlay; Picaridin

Indexed keywords

COMPUTATIONAL CHEMISTRY; DENSITY FUNCTIONAL THEORY; MOLECULAR MECHANICS; QUANTUM CHEMISTRY;

3-D QSAR; AB INITIO CALCULATIONS; AI3-37220; DIASTEREOISOMERS; MOSQUITO REPELLENTS; OPTIMIZED GEOMETRIES; OVERLAY; PICARIDIN; ROOT-MEAN-SQUARE DISTANCES; STRUCTURE-ACTIVITY RELATIONSHIPS;

GEOMETRY;

HEXAPODA;

EID: 34249068496     PISSN: 1062936X     EISSN: 1029046X     Source Type: Journal    
DOI: 10.1080/10629360701303784     Document Type: Article

References (32)

1. M. Debboun, D.A. Strickman, J.A. Klun. J. Am. Mosq. Control Assoc., 21, 4 (2005).
2. R.J. Novak, E.J. Gerberg. J. Am. Mosq. Control Assoc., 21, 7 (2005).
3. E.T. McCabe, W.F. Barthel, S.I. Gertler, S.A. Hall. J. Org. Chem., 19, 493 (1954).
4. L. Goodyer, R.H. Behrens. Am. J. Trop. Med. Hyg., 59, 323 (1998).
5. M.S. Fradin. Ann. Intern. Med., 128, 931 (1998).
6. United States Environmental Protection Agency. OPPTS. Reregistration Eligibility Decision: DEBT. 1998, EPA738-R-98-010: 1-118. Available online at: http://www.epa.gov/oppsrrd1/REDs/0002red.pdf (accessed 11 May 2006).
7. T.P. McGovern, C.E. Schreck, J. Jackson. Mosq. News, 38, 346 (1978).
8. S.P. Frances, T.A. Klein, D.W. Hildebrandt, R. Burge, N. Chumnong, E. Nantana, S. Boonsong, R.A. Wirtz. J. Med. Entomol., 33, 511 (1996).
9. T.W. Walker, L.L. Robert, R.A. Copeland, A.W. Githeko, R.A. Wirtz, J.I. Githure, T.A. Klein. J. Am. Mosq. Control Assoc., 12, 172 (1996).
10. S.P. Frances, R.D. Cooper, A.W. Sweeney. J. Med. Entomol., 35, 690 (1998).
11. S.P. Frances, R.D. Cooper, S. Popat, N.W. Beebe. J. Am. Mosq. Control Assoc., 17, 42 (2001).
12. M.J. Perich, D. Strickman, R.A. Wirtz, S.A. Stockwell, J.I. Glick, R. Burge, G. Hunt, P.G. Lawyer. J. Med. Entomol., 32, 306 (1995).
13. L.L. Robert, R.E. Coleman, D.A. Lapointe, P.J.S. Martin, R. Kelly, J.D. Edman. J. Med. Entomol., 29, 267 (1992).
14. J. Boeckh, H. Breer, M. Geier, F.-P. Hoever, B.-W. Kruger, G. Nentwig, H. Sass. Pestic. Sci., 48, 359 (1996).
15. http://www.epa.gov/opprd001/factsheets/
16. A.K. Bhattacharjee, R.K. Gupta, D. Ma, J.M. Karle. J. Mol. Recog., 13, 213 (2000).
17. D. Ma, A.K. Bhattacharjee, R.K. Gupta, J.M. Karle. Am. J. Trop. Med. Hyg., 60, 1 (1999).
18. A.K. Bhattacharjee, W. Dheranetra, D.A. Nichols, R.K. Gupta. QSAR Comb. Sci., 24, 593 (2005).
19. J.A. Klun, W.F. Schmidt, M. Debboun. J. Med. Entomol., 38, 809 (2001).
20. R. Natarajan, S.C. Basak, A.T. Balaban, J.A. Klun, W.F. Schmidt. Pest Manag. Sci., 61, 1193 (2005).
21. J.A. Klun, A. Khrimian, M. Debboun. J. Med. Entomol., 43, 34 (2006).
22. J.F. Carroll, J.A. Klun, M. Debboun. Med. Vet. Entomol., 19, 101 (2005).
23. J.A. Klun, M. Debboun. J. Med. Entomol., 37, 177 (2000).
24. Chem3D Ultra v.8.0, Cambridge Soft Corporation, Cambridge, MA, USA (2004).
25. U. Burkert, N.L. Allinger. Molecular Mechanics, American Chemical Society, Washington, DC (1982).
26. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, J.J.P. Stewart. J. Am. Chem. Soc., 107, 3902 (1985).
27. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, A. Pople. Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford, CT (2004).
28. C.T. Lee, W.T. Yang, R.G. Parr. Phys. Rev. B, 37, 785 (1988);
29. A.D. Becke. Phys. Rev. A, 38, 3098 (1988).
30. W. Koch, M.C. Holthausen. A Chemist's Guide to Density Functional Theory, Wiley-VCH, Weinheim, Germany (2000).
31. W. Humphrey, A. Dalke, K. Schulten. J. Molec. Graphics, 14, 33 (1996).
32. M. Thomson and Planaria Software, ArgusLab v. 4.0.1 (2004).