CoMFA methodology in structure-activity analysis of hexahydro- and octahydropyrido[1,2-c]pyrimidine derivatives based on affinity towards 5-HT1A, 5-HT2A and α1-adrenergic receptors

Journal of Molecular Graphics and Modelling

Volumn 25, Issue 3, 2006, Pages 353-362

  Maciejewska, Dorota ^a   Zołek, Teresa ^a   Herold, Franciszek ^a  

^a MEDICAL UNIVERSITY OF WARSAW   (Poland)

Author keywords

CoMFA methodology; Hexahydro and octahydropyrido 1,2 c pyrimidines

Indexed keywords

COMFA METHODOLOGY; HEXAHYDRO- AND OCTAHYDROPYRIDO[1,2-C]PYRIMIDINES;

COMPUTER SIMULATION; MATHEMATICAL MODELS; MOLECULAR STRUCTURE; NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL);

DERIVATIVES;

ALPHA 1 ADRENERGIC RECEPTOR; PYRIMIDINE DERIVATIVE; SEROTONIN 1A RECEPTOR; SEROTONIN 2A RECEPTOR;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CHEMICAL MODEL; COMPARATIVE MOLECULAR FIELD ANALYSIS; CONFORMATION; MOLECULAR INTERACTION; NONHUMAN; PRIORITY JOURNAL; PROTON TRANSPORT; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRIMIDINES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTOR, SEROTONIN, 5-HT1A; RECEPTOR, SEROTONIN, 5-HT2A; RECEPTORS, ADRENERGIC, ALPHA-1; SPIRO COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33750048725     PISSN: 10933263     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jmgm.2006.02.002     Document Type: Article

References (34)

1. 1A agonists measured with the forces swim test. Psychopharmacology 101 (1990) 497-504
2. Romero A.G., and McCall R.B. In: Bristol J.A. (Ed). Advances in Medicinal Chemistry vol. 27 (1991), Academic Press, New York Chapter 3
3. Barnes N.M., and Sharp T. A review of central 5-HT receptors and their function. Neuropharmacology 38 (1999) 1083-1152
4. Taylor D.P., and Moon S.L. Buspirone and related compounds as alternative anxiolytics. Neuropeptides 19 (1991) 15-19
5. 1-arylpiperazines. J. Med. Chem. 40 (1997) 300-312
6. 1A affinity/selectivity. J. Med. Chem. 42 (1999) 36-49
7. Hamon M. Serotoninergic neurons and 5-HT receptors in CNS. In: Baumgarten H.G., and Göthert M. (Eds). Handbook of Experimental Pharmacology (1997), Springer, Berlin
8. Zifa E., and Fillion G. 5-hydroxyttyptamine receptors. Pharmacol. Rev. 44 (1992) 401-458
9. Saudou F., and Hen R. 5-HT receptor subtype: molecular and functional diversity. Med. Chem. Res. 4 (1994) 16-84
10. Hoyer D., Fozard J.R., Mylecharane E.J., Clarke D.E., Martin G.R., and Humphrey P.P.A. New classification of receptors for 5-hydroxytryptamine (Serotonin). Pharmacol. Rev. 46 (1994) 153-203
11. Verges D., and Calas A. Serotoninergic neurons and serotonin receptors: gains from cytochemical approaches. J. Chem. Neuroanat. 18 (2000) 41-56
12. Perez D.M., Hwa J., Gaivin R., Mathur M., Brown F., and Graham R.M. Constitutive activation of single effector pathway: evidence for multiple activation states of a G protein-coupled receptor. Mol. Pharmacol. 49 (1996) 112-122
13. Sidhu A., and Niznik H.B. Coupling of dopamine receptor subtypes to multiple and diverse G proteins. Int. J. Dev. Neurosci. 18 (2000) 669-677
14. Trumpp-Kallmeyer S., Hoflack J., Bruinvels A., and Hibert M. Modeling of G-protein-Coupled receptors: application to dopamine, adrenaline, serotonin, acetylcholine, and mammalian opsin receptors. J. Med. Chem. 35 (1992) 3448-3456
15. Browne L.J., and Shaw K.J. New Anxiolytics. In: Bristol J.A. (Ed). Annual Reports in Medicinal Chemistry vol. 26 (1991), Academic Press, New York pp. 1-10
16. 1-adrenergic affinity. J. Med. Chem. 34 (1991) 2633-2638
17. 2A receptors. Il Farmaco 57 (2002) 959-971
18. 2A receptors, part 2. Pharmazie 59 (2004) 99-105
19. Herold F., Król M., Kleps J., and Nowak G. Synthesis of new hexahydro- and octahydropyrido[1,2-c]pyrimidine derivatives with an arylpiperazine moiety as ligands for 5-HT1A and 5-HT2A receptors, part 4. Eur. J. Med. Chem. 41 (2006) 125-134
20. Cramer III R.D., Petterson D.E., and Bunce J.D. Comparative molecular fields analysis (CoMFA). I. Effect of shape on binding of steroids to carrier proteins. J. Med. Chem. 110 (1988) 5959-5967
21. Cramer III R.D., DePriest S.A., Patterson D.E., and Hecht P. The developing practice of comparative molecular fields analysis. In: Kubinyi H. (Ed). 3D QSAR in Drug Design, Theory, Methods and Applications (1993), ESCOM Science Publishers, Leiden 443-485
22. In: Kubinyi H., Folkers G., and Martin Y.C. (Eds). 3D QSAR in Drug Design vols. 2/3 (1998), Kluwer, Dordrecht
23. 1-receptors. A comparison of comfa models. J. Med. Chem. 40 (1997) 1648-1656
24. Yamagami C., Motohashi N., and Akamatsu M. Quantum chemical- and 3-D-QSAR (CoMFA) studies of benzalacetones and 1,1,1-trifluoro-4-phenyl-3-buten-2-ones. Bioorg. Med. Chem. Lett. 12 (2002) 2281-2285
25. Purnima M.S., Vos de D., Raveedra D., Sarma J.A.R.P., and Sujit R. 3-D QSAR studies on new dibenzyltin(IV) anticancer agents by comparative molecular field analysis (CoMFA). Bioorg. Med. Chem. Lett. 12 (2002) 61-64
26. Sybyl 7.0 package, Tripos Inc., USA, 2004.
27. Pisklak M., Herold F., Anulewicz-Ostrowska R., and Wawer I. Structural studies of 4-aryloctahydro-pyrido[1,2-c]pyrimidine derivatives. J. Mol. Struct. 605 (2002) 85-92
28. Huang M., Yang D.-Y., Shang Z., Zou J., and Yu Q. 3D-QSAR studies on 4-hydroxyphenylpuruvate dioxygenase inhibitors by comparative molecular field analysis (CoMFA). Bioorg. Med. Chem. Lett. 12 (2002) 2271-2275
29. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery Jr. J.A., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Baboul A.G., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Gonzalez C., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S., and Pople J.A. Gaussian 98, Revision A. 7 (1998), Gaussian Inc., Pittsburgh, PA
30. 1A receptor. Eur. J. Pharm. 416 (2001) 33-41
31. 1A receptor ligands from crystallographic data. Updated model of the receptor pharmacophore. Arch. Pharm. Pharm. Med. Chem. 330 (1997) 146-160
32. 1A-receptor agonists based on stereoselective methyl-substituted and conformationally restricted analogues of 8-hydroxy-2-(dipropyloamino) tetralin. J. Med. Chem. 34 (1991) 497-510
33. HyperChem 7.02, HyperCube Inc., 2002.
34. Viswanadhan V.N., Ghose A.K., Revankar G.N., and Robins R.K. Atomic physicochemical parameters for three dimensional structure directed quantitative structure-activity relationships. 4. Additional parameters for hydrophobic and dispersive interactions and their application for an automated superposition of certain naturally occurring nucleoside antibiotics. J. Chem. Inf. Comput. Sci. 29 (1989) 163-172