The influence of R and S configurations of a series of amphetamine derivatives on quantitative structure-activity relationship models

Analytica Chimica Acta

Volumn 759, Issue , 2013, Pages 43-52

  Fresqui, Maíra A C ^a   Ferreira, Márcia M C ^b   Trsic, Milan ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Amphetamine derivatives; Electronic; Hydrophobic and steric descriptors; Quantitative structure activity relationship; R and S configurations of amphetamines

Indexed keywords

AMPHETAMINE DERIVATIVES; DESCRIPTORS; ELECTRONIC; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; R AND S CONFIGURATIONS OF AMPHETAMINES;

ENZYMES; HYDROPHOBICITY; STEREOCHEMISTRY;

COMPUTATIONAL CHEMISTRY;

AMPHETAMINE DERIVATIVE;

ARTICLE; BINDING SITE; CHEMOMETRIC ANALYSIS; DRUG STRUCTURE; ELECTROPHILICITY; MOLECULAR DOCKING; MOLECULAR INTERACTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

AMPHETAMINE; ANIMALS; CENTRAL NERVOUS SYSTEM STIMULANTS; HUMANS; MOLECULAR CONFORMATION; MOLECULAR DOCKING SIMULATION; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RATS; STEREOISOMERISM;

EID: 84871377747     PISSN: 00032670     EISSN: 18734324     Source Type: Journal    
DOI: 10.1016/j.aca.2012.11.004     Document Type: Article

References (54)

1. Berman S.M., Kuczenski R., McCracken J.T., London E.D. Mol. Psychiatry 2009, 14:123.
2. Madras B.K., Miller G.M., Fischman A.I. Biol. Psychiatry 2005, 57:1397.
3. Knoll J. Med. Res. Rev. 1992, 12:505.
4. Mitchell D.J., Nikolic D., Rivera E., Sablin S.O., Choi S., van Breemen R.B., Singer T.P., Silverman R.B. Biochemistry 2001, 40:5447.
5. Chimenti F., Secci D., Bolasco A., Chimenti P., Bizzarri B., Granese A., Carradori S., Yanez M., Orallo F., Ortuso F., Alcaro S. J. Med. Chem. 2009, 52:1935.
6. Ogunrombi M.O., Malan S.F., Terre'Blanche G., Castagnoli N., Bergh J.J., Petzer J.P. Bioorg. Med. Chem. 2008, 16:2463.
7. La Regina G., Silvestri R., Gatti V., Lavecchia A., Novellino E., Befani O., Turini P., Agostinelli E. Bioorg. Med. Chem. 2008, 16:9729.
8. Scorza M.C., Carrau C., Silveira R., ZapataTorres G., Cassels B.K., ReyesParada M. Biochem. Pharmacol. 1997, 54:1361.
9. Vallejos G., Rezende M.C., Cassels B.K. J. Comput.-Aided Mol. Des. 2002, 16:95.
10. Binda C., Li M., Hubalek F., Restelli N., Edmondson D.E., Mattevi A. Proc. Natl. Acad. Sci. U. S. A. 2003, 100:9750.
11. Subramanian S., Ferreira M.M.C., Trsic M. Struct. Chem. 1998, 9:47.
12. Fukui K. Science 1982, 218:747.
13. Fukui K. Angew. Chem. Int. Ed. 1982, 21:801.
14. da Silva R.R., Ramalho T.C., Santos J.M., Figueroa-Villar J.D. J. Phys. Chem. A 2006, 110:1031.
15. da Costa E.B., Trsic M. J. Mol. Graphics Modell. 2010, 28:657.
16. Ferreira M.M.C. J. Braz. Chem. Soc. 2002, 13:742.
17. Hurtado-Guzman C., Fierro A., Iturriaga-Vasquez P., Sepulveda-Boza S., Cassels B.K., Reyes-Parada M. J. Enzyme Inhib. Med. Chem. 2003, 18:339.
18. Sterling J., Herzig Y., Goren T., Finkelstein N., Lerner D., Goldenberg W., Miskolczi I., Molnar S., Rantal F., Tamas T., Toth G., Zagyva A., Zekany A., Lavian G., Gross A., Friedman R., Razin M., Huang W., Krais B., Chorev M., Youdim M.B., Weinstock M. J. Med. Chem. 2002, 45:5260.
19. Son S.Y., Ma A., Kondou Y., Yoshimura M., Yamashita E., Tsukihara T. Proc. Natl. Acad. Sci. U. S. A. 2008, 105:5739.
20. Morimoto B.H., Lovell S., Kahr B. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 1998, 54:229.
21. Salach J.I. Arch. Biochem. Biophys. 1979, 192:128.
22. Romeiro L.A.S., Fraga C.A.M., Barreiro E.J. Quim. Nova 2003, 26:347.
23. Salach J.I., Detmer K., Youdim M.B.H. Mol. Pharmacol. 1979, 16:234.
24. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P.Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. Montgomery, J. A. J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N.J. Millam, M. Klene, J.E. Knox, 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, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian, Inc., Wallingford, CT, 2003.
25. Tetko I.V., Gasteiger J., Todeschini R., Mauri A., Livingstone D., Ertl P., Palyulin V., Radchenko E., Zefirov N.S., Makarenko A.S., Tanchuk V.Y., Prokopenko V.V. J. Comput.-Aided Mol. Des. 2005, 19:453.
26. VCCLAB, 2005. http://www.vcclab.org/.
27. MarvinSketch5.9.0, 2012-03-02, trial version.
28. Beebe R.P.K., Seasholtz M.B. Chemometrics: A Practical Guide 1998, John Wiley & Sons, New York.
29. Pirouette Software Version 3 2007, Infometrix Inc., USA.
30. Dewar M.J.S., Zoebisch E.G., Healy E.F., Stewart J.J.P. J. Am. Chem. Soc. 1985, 107:3902.
31. Roothaan C.C.J. Rev. Mod. Phys. 1951, 23:69.
32. Roothaan C.C.J. Rev. Mod. Phys. 1960, 32:179.
33. Hohenberg P., Kohn W. Phys. Rev. B 1964, 136:B864.
34. Kohn W., Sham L.J. Phys. Rev. 1965, 140:A1133.
35. Becke A.D. J. Chem. Phys. 1993, 98:5648.
36. Lee C.T., Yang W.T., Parr R.G. Phys. Rev. B 1988, 37:785.
37. Moller C., Plesset M.S. Phys. Rev. 1934, 46:0618.
38. HyperChem Software Version 7.1 2002, Hyper Co., USA.
39. Breneman C.M., Wiberg K.B. J. Comput. Chem. 1990, 11:361.
40. Pearson R.G. Proc. Natl. Acad. Sci. U. S. A. 1986, 83:8440.
41. Parr R.G., Von Szentpaly L., Liu S.B. J. Am. Chem. Soc. 1999, 121:1922.
42. Chen P., Fujisawa K., Solomon E.I. J. Am. Chem. Soc. 2000, 122:10177.
43. Teofilo R.F., Martins J.P.A., Ferreira M.M.C. J. Chemometr. 2009, 23:32.
44. Bratchell N. J. Chemometr. 1997, 11:93.
45. Golbraikh A., Tropsha A. J. Mol. Graphics Modell. 2002, 20:269.
46. Kiralj R., Ferreira M.M.C. J. Braz. Chem. Soc. 2009, 20:770.
47. Tropsha A., Gramatica P., Gombar V.K. QSAR Comb. Sci. 2003, 22:69.
48. Kiralj R., Ferreira M.M.C. J. Chemometr. 2010, 24:681.
49. Trott O., Olson A.J. J. Comput. Chem. 2010, 455.
50. De Colibus L., Li M., Binda C., Lustig A., Edmondson D.E., Mattevi A. Proc. Natl. Acad. Sci. U. S. A. 2005, 102:12684.
51. Guo H., Karplus M. J. Chem. Phys. 1989, 91:1719.
52. Moran D., Simmonett A.C., Leach F.E., Allen W.D., Schleyer P.V., Schaefer H.F. J. Am. Chem. Soc. 2006, 128:9342.
53. Eriksson L., Jaworska J., Worth A.P., Cronin M.T.D., McDowell R.M., Gramatica P. Environ. Health Perspect. 2003, 111:1361.
54. Allinger N.L., Zhou X.F., Bergsma J. Theochem - J. Mol. Struct. 1994, 118:69.