On substituent effect on the benzodiazepinone system

Computational and Theoretical Chemistry

Volumn 993, Issue , 2012, Pages 13-19

  Karpińska, Grazyna ^a   Mazurek, Aleksander P ^a,b   Dobrowolski, Jan Cz ^a,c  

^a NATIONAL MEDICINES INSTITUTE   (Poland)

^b MEDICAL UNIVERSITY OF WARSAW   (Poland)

^c INDUSTRIAL CHEMISTRY RESEARCH INSTITUTE   (Poland)

Author keywords

AIM; Aromaticity; Benzodiazepinones; PEDA; Substituent effect

Indexed keywords

EID: 84863869782     PISSN: 2210271X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.comptc.2012.05.019     Document Type: Article

References (37)

1. Leimgruber W., Stefanov V., Schenker F., Karr A., Berger J. Isolation and characterization of anthramycin a new antitumor antibiotic. J. Am. Chem. Soc. 1965, 87:5791-5793.
2. Leimgruber W., Batcho A.D., Schenker F. Structure of anthramycin. J. Am. Chem. Soc. 1965, 87:5793-5795.
3. Leimgruber W., Batcho A.D., Czajkowski R.C. Total synthesis of anthramycin. J. Am. Chem. Soc. 1968, 90:5641-5643.
4. Möller H.J. Effectiveness and safety of benzodiazepines. J. Clin. Psychopharmacol. 1999, 19:2S-11S.
5. Katzung B.G. Basic and Clinical Pharmacology 2004, Lange Medical Books/McGraw-Hill, p. 878. ninth ed.
6. Shader R.I., Greenblatt D.J. Use of benzodiazepines in anxiety disorders. New Engl. J. Med. 1993, 328:1398-1405.
7. Millefiori S., Alparone A. Electronic properties of neuroleptics: ionization energies of benzodiazepines. J. Mol. Model 2011, 17:281-287.
8. Zajac M., Pawełczyk E. Medicinal Chemistry (in Polish) 2000, Medical Academy, Poznan.
9. Macdonald R.L., Olsen R.W. GABA receptor channel. Ann. Rev. Neurosci. 1994, 17:569-602.
10. Villar H.O., Davies M.F., Loew G.H., Maguire P.A. Molecular models for recognition and activation at the benzodiazepine receptor: a review. Life Sci. 1991, 48:593-602.
11. Hadjipavlou-Litina D., Garg R., Hansch C. Comparative quantitative structure-activity relationship studies (QSAR) on non-benzodiazepine compounds binding to benzodiazepine receptor (BZR). Chem. Rev. 2004, 104:3751-3793.
12. Morshed M.N., Neaz M.M., Muddassar M., Pasha F.A., Cho S.J. 2D-QSAR of non-benzodiazepines to benzodiazepines receptor (BZR). Med. Chem. Res. 2009, 18:98-111.
13. Ci S., Ren T., Su Z. Investigating the putative binding-mode of GABA and diazepam within GABA(A) receptor using molecular modeling. Protein J. 2008, 27:71-78.
14. Thakur M., Ojha L., Thakur A., Solanki B.K. Study of active site and sar on some benzodiazepines. J. Comput. Biol. Bioinform. Res. 2010, 2:10-19.
15. Ozimiński W.P., Dobrowolski Jan Cz. On the substituent effect. The natural population analysis approach. J. Phys. Org. Chem. 2009, 22:769-778.
16. Becke A.D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 1993, 98:5648-5652.
17. Lee C., Yang W., Parr R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev., B 1988, 37:785-789.
18. Janoschek R.R. Quantum chemical B3LYP/cc-pvqz computation of ground-state structures and properties of small molecules with atoms of Z≤18 (hydrogen to argon). Pure Appl. Chem. 2001, 73:1521-1553.
19. Krishnan R., Binkley J.S., Seeger R., Pople J.A. Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions. J. Chem. Phys. 1980, 72:650-654.
20. McLean A.D., Chandler G.S. Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z=11-18. J. Chem. Phys. 1980, 72:5639-5648.
21. Blaudeau J.-P., McGrath M.P., Curtiss L.A., Radom L. Extension of Gaussian-2 (G2) theory to molecules containing third-row atoms K and Ca. J. Chem. Phys. 1997, 107:5016-5021.
22. Curtiss L.A., McGrath M.P., Blandeau J.-P., Davis N.E., Binning R.C., Radom L. Extension of Gaussian-2 theory to molecules containing third-row atoms Ga-Kr. J. Chem. Phys. 1995, 103:6104-6113.
23. Glukhovstev M.N., Pross A., McGrath M.P., Radom L. Extension of Gaussian-2 (G2) theory to bromine - and iodine - containing molecules: use of effective core potentials. J. Chem. Phys. 1995, 103:1878-1885.
24. Gaussian 03, Revision B.04, 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, 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, J.A. Pople, Gaussian, Inc., Pittsburgh PA, 2003.
25. E.D. Glendening, A.E. Reed, J.E. Carpenter, F. Weinhold, NBO Ver 3.1 (included in the Gaussian 03 package of programs).
26. Reed A.E., Curtiss L.A., Weinhold F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem. Rev. 1988, 88:899-926.
27. Reed A.E., Weinhold F. Natural bond orbital analysis of internal rotation barriers and related phenomena. Isr. J. Chem. 1991, 31:277-285.
28. Roman M., Dobrowolski J.Cz., Baranska M. Theoretical modeling of molecular spectra parameters of disubstituted diacetylenes. J. Chem. Inform. Model 2011, 51:283-295.
29. Kruszewski J., Krygowski T.M. Definition of aromaticity basing on the harmonic oscillator model. Tetrah. Lett. 1972, 13:3839-3942.
30. Krygowski T.M., Cyrański M.K. Structural aspects of aromaticity. Chem. Rev. 2001, 101:1385-1420.
31. Cyranski M.K. Energetic aspects of cyclic pi-electron delocalization: evaluation of the methods of estimating aromatic stabilization energies. Chem. Rev. 2005, 105:3773-3811.
32. Krygowski T.M., Cyrański M.K. Separation of the energetic and geometric contributions to the aromaticity. Part IV. A general model for the π-electron systems. Tetrahedron 1996, 52:10255-10264.
33. Popelier P.L.A. Atoms in Molecules. An Introduction. vol. 659 2000, Prentice-Hall, Harlow, England.
34. AIM2000, University of Applied Sciences, Bielefeld, Germany, 2000.
35. Krygowski T.M., Ejsmont K., Stepień B.T., Cyrański M.K., Poater J., Sola M. Relation between the substituent effect and aromaticity. J. Org. Chem. 2004, 69:6634-6640.
36. Krygowski T.M., Stepień B.T. Sigma- and pi-electron delocalization: focus on substituent effects. Chem. Rev. 2005, 105:3482-3512 36.
37. Krygowski T.M., Dobrowolski M.A., Zborowski K., Cyranski M.K. Relation between the substituent effect and aromaticity. Part II. The case of meta- and para-homodisubstituted benzene derivatives. J. Phys. Org. Chem. 2006, 19:889-895.