Application of desirability-based multi(bi)-objective optimization in the design of selective arylpiperazine derivates for the 5-HT1A serotonin receptor

European Journal of Medicinal Chemistry

Volumn 44, Issue 12, 2009, Pages 5045-5054

  Machado, A ^a   Tejera, E ^a   Cruz Monteagudo, M ^b,c   Rebelo, I ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b CENTRAL UNIVERSITY OF LAS VILLAS   (Cuba)

^c UNIVERSITY OF PORTO   (Portugal)

Author keywords

Arylpiperazine; Desirability; Drug design; Inverse QSAR; Multiobjective optimization; Serotonin receptor

Indexed keywords

PIPERAZINE DERIVATIVE; SEROTONIN 1A RECEPTOR; SEROTONIN 2A AGONIST;

ARTICLE; BINDING SITE; CLINICAL ASSESSMENT TOOL; COMPARATIVE STUDY; CORRELATION ANALYSIS; DRUG DESIGN; DRUG SCREENING; DRUG STRUCTURE; PHARMACOPHORE; PROTEIN BINDING; PROTEIN STRUCTURE; PROTEIN STRUCTURE, FUNCTION AND VARIABILITY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

DRUG DESIGN; MODELS, BIOLOGICAL; MOLECULAR STRUCTURE; PIPERAZINES; PROTEIN BINDING; RECEPTOR, SEROTONIN, 5-HT1A; RECEPTOR, SEROTONIN, 5-HT2A;

EID: 70449651676     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.09.008     Document Type: Article

References (44)

1. Kuipers W., Van Wijngaarden I., Kruse C.G., Ter Horst-Van Amstel M., Th. M. Tulp M., and IJzerman A.P. J. Med. Chem. 38 (1995) 1942-1954
2. Capela J.P., Fernandes E., Remião F., Bastos M.L., Meisel A., and Carvalho F. NeuroToxicology (2007)
3. Barnes N.M., and Sharp T. Neuropharmacology 38 (1999) 1083-1152
4. Hoyer D., Hannon J.P., and Martin G.R. Pharmacol. Biochem. Behav. 71 (2002) 533-554
5. Tricklebank M.D. Trends Pharmacol. Sci. 6 (1985) 403-407
6. Jurczyk S., Kołaczkowski M., Maryniak E., Zajdel P., Pawłowski M., Tatarczynska E., Kłodzinska A., Chojnacka-Wójcik E., Bojarski A., Charakchieva-Minol S., Duszynska B., Nowak G., and Maciaü D. J. Med. Chem. 47 (2004) 2659-2666
7. Gaillard P., Carrupt P.-A., Testa B., and Schambel P. J. Med. Chem. 39 (1996) 126-134
8. Orús L., Pérez-Silanes S., Oficialdegui A., Martínez-Esparza J., Castillo J., Mourelle M., Langer T., Guccione S., Donzella G., Krovat E., Poptodorov K., Lasheras B., Ballaz S., Hervías I., Tordera R., Río J., and Monge A. J. Med. Chem. 45 (2002) 4128-4139
9. López-Rodríguez M.L., Ayala D., Benhamú B., Morcillo M.J., and Viso A. Curr. Med. Chem. 9 (2002) 443-469
10. Centurión D., Ortiz M., Saxena P., and Villalón C. Br. J. Pharmacol. 135 (2002) 1531-1539
11. Brea J., Rodrigo J., Carrieri A., Sanz F., Cadavid M., Enguix M., Villazón M., Mengod G., Caro Y., Masaguer C., Ravina E., Centeno N., Carotti A., and Loza M. J. Med. Chem. 45 (2002) 54-71
12. Chambers J., and Nichols D. J. Comput. Aided Mol. Des. 16 (2002) 511-520
13. Hamacher A., Weigt M., Wiese1 M., Hoefgen B., Lehmann J., and Kassack M. BMC. Pharmacol. 6 (2006) 11
14. Handl J., Kell D., and Knowles J. IEEE/ACM Trans. Comput. Biol. Bioinform. 4 (2007) 279-292
15. Nicolotti O., Gillet V., Fleming P., and Green D. J. Med. Chem. 45 (2002) 5069-5080
16. Brown N., McKay B., and Gasteiger J. J. Comput. Aided Mol. Des. 20 (2006) 333-341
17. Janson S., Merkle D., and Middendorf M. Appl. Soft Comput. 8 (2008) 666-675
18. Derringer G., and Suich R. J. Qual. Technol. 12 (1980) 214-219
19. Singh J., Ator M., Jaeger E., Allen M., Whipple D., Soloweij J., Chowdhary S., and Treasurywala A. J. Am. Chem. Soc. 118 (1996) 1669-1676
20. Sheridan R., and Kearsley S. J. Chem. Inf. Comput. Sci. 35 (1995) 310-320
21. Rao S., and Stockfisch T. J. Chem. Inf. Comput. Sci. 43 (2003) 1614-1622
22. Leopoldo M., Lacivita E., Contino M., Colabufo N.A., Berardi F., and Perrone R. J. Med. Chem. 50 (2007) 4214-4221
23. Cruz-MonteAgudo M., Borges F., and Cordeiro M. J. Comput. Chem. 29 (2008) 2445-2459
24. Grundt P., Prevatt K.M., Cao J., Taylor M., Floresca C.Z., Choi J., Jenkins B.G., Luedtke R.R., and Newman A.H. J. Med. Chem. 50 (2007) 4135-4146
25. Bojarski A.J., Kowalski P., Kowalska T., Duszynska B., Charakchieva-Minol S., Tatarczynska E., Klodzinska A., and Chojnacka-Wójcik E. Bioorg. Med. Chem. 10 (2002) 3817-3827
26. Chem Draw Ultra 9.0. Cambridge Soft. 2004.
27. Frank J. MOPAC 2.0 (1993), Seiler Research Laboratory, US Air Force Academy, Colorado Springs version 2.0
28. Tetko I.V. Drug. Discov. Today. 10 (2005) 1497-1500
29. Tetko I.V., Gasteiger J., Todeschini R., Mauri A., Livingstone D., Ertl P., Palyulin V.A., Radchenko E.V., Zefirov N.S., Makarenko A.S., Tanchuk V.Y., and Prokopenko V.V.J. Comput. Aid. Mol. Des 19 (2005) 453-463
30. Tetko I.V., Kovalishyn V.V., and Livingstone D.J. J. Med. Chem. 44 (2001) 2411-2420
31. Tetko I.V., Luik A.I., and Poda G.I. J. Med. Chem. 36 (1993) 811-814
32. Cavill R., Keun H.C., Holmes E., Lindon J.C., Nicholson J.K., and Ebbels T.M.D. Bioinformatics 25 (2009) 112-118
33. Yasri A., Hartsough D., and Chem J. Inf. Comput. Sci. 41 (2001) 1218-1227
34. Todeschini R., Consonni V., Mauri A., and Pavan M. Anal. Chim. Acta 515 (2004) 199-208
35. Todeschini R., Consonni V., and Pavan M. Chemom. Intell. Lab. Syst. 70 (2004) 55-61
36. Wehrens R., Putter H., and Buydens L.M.C. Chemom. Intell. Lab. Syst. 54 (2000) 35-52
37. STATISTICA 6.0 Statsoft_Inc.; 2001.
38. Young D.C. Computational Chemistry: A Practical Guide for Applying Techniques to Real-World Problems (2001), John Wiley & Sons, Inc.
39. Gramatica P. QSAR Comb. Sci. 5 (2007) 694-701
40. Tudor I., and Opera. Chemoinformatics in Drugs Discovery vol. 13 (2005), Wiley, Weinheim
41. Mellin C., Vallgárda J., Nelson D.L., Bjork L., Yu H., Andén N.E., Csoregh I., Arvidsson L.E., and Hacksell U. J. Med. Chem. 34 (1991) 497-510
42. Chilmonczyk Z., Szelejewska-Wozniakowska A., Cybulski J., Cybulski M., Kozio A., and Gdaniec M. Arch. Pham. Pham. Med. Chem. 330 (1997) 146-160
43. Ladduwahetty T., Boase A.L., Mitchinson A., Quin C., Patel S., Chapman K., and MacLeod A.M. Bioorg Med Chem Lett 16 (2006) 3201-3204
44. Chidester C.G., Lin C., Lahti R.A., Haadsma-Svensson S.R., and Smith M.W. J. Med. Chem. 36 (1993) 10