Table of Contents
Journal of Theoretical Chemistry
Volume 2014 (2014), Article ID 624891, 13 pages
http://dx.doi.org/10.1155/2014/624891
Research Article

Mathematical Analysis of a Series of 4-Acetylamino-2-(3,5-dimethylpyrazol-1-yl)-6-pyridylpyrimidines: A Simple Way to Relate Quantum Similarity to Local Chemical Reactivity Using the Gaussian Orbitals Localized Theory

1Grupo de Química Cuántica y Teórica, Programa de Química, Facultad de Ciencias Exactas y Naturales, Universidad de Cartagena, Cartagena de Indias, Colombia
2Departamento de Ciencias Químicas, Universidad Nacional Andres Bello, Republica 275, 8370146 Santiago, Chile
3Facultad de Medicina, Corporación Universitaria Rafael Núñez, Cartagena, Colombia

Received 16 September 2013; Revised 13 January 2014; Accepted 14 January 2014; Published 16 April 2014

Academic Editor: Mihai V. Putz

Copyright © 2014 Alejandro Morales-Bayuelo et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. J. Jankovic, “Parkinson’s disease: clinical features and diagnosis,” Journal of Neurology, Neurosurgery & Psychiatry, vol. 79, pp. 368–376, 2008. View at Publisher · View at Google Scholar
  2. C. A. Davie, “A review of Parkinson's disease,” British Medical Bulletin, vol. 86, no. 1, pp. 109–127, 2008. View at Publisher · View at Google Scholar · View at Scopus
  3. M. Barnett-Cowan, R. T. Dyde, S. H. Fox, E. Moro, W. D. Hutchison, and L. R. Harris, “Multisensory determinants of orientation perception in Parkinson's disease,” Neuroscience, vol. 167, no. 4, pp. 1138–1150, 2010. View at Publisher · View at Google Scholar · View at Scopus
  4. D. Garcia-Borreguero, O. Larrosa, and M. Bravo, “Parkinson's disease and sleep,” Sleep Medicine Reviews, vol. 7, no. 2, pp. 115–129, 2003. View at Publisher · View at Google Scholar · View at Scopus
  5. M. Vaugoyeau, S. Viel, C. Assaiante, B. Amblard, and J. P. Azulay, “Impaired vertical postural control and proprioceptive integration deficits in Parkinson's disease,” Neuroscience, vol. 146, no. 2, pp. 852–863, 2007. View at Publisher · View at Google Scholar · View at Scopus
  6. D. Aarsland, E. Londos, and C. Ballard, “Parkinson's disease dementia and dementia with Lewy bodies: different aspects of one entity,” International Psychogeriatrics, vol. 21, no. 2, pp. 216–219, 2009. View at Publisher · View at Google Scholar · View at Scopus
  7. L. M. de Lau and M. M. Breteler, “Epidemiology of Parkinson's disease,” The Lancet Neurology, vol. 5, no. 6, pp. 525–535, 2006. View at Publisher · View at Google Scholar · View at Scopus
  8. X. Zhang, J. E. Tellew, Z. Luo et al., “Lead optimization of 4-acetylamino-2-(3,5-dimethylpyrazol-1-yl)-6- pyridylpyrimidines as A2A adenosine receptor antagonists for the treatment of Parkinson's disease,” Journal of Medicinal Chemistry, vol. 51, no. 22, pp. 7099–7110, 2008. View at Publisher · View at Google Scholar · View at Scopus
  9. R. Carbó-Dorca and L. Mercado, “Commentaries on quantum similarity (1): density gradient quantum similarity,” Journal of Computational Chemistry, vol. 31, pp. 2195–2212, 2010. View at Publisher · View at Google Scholar
  10. R. Carbó-Dorca, E. Besalú, and L. Mercado, “Communications on quantum similarity, part 3: a geometric-quantum similarity molecular superposition algorithm,” Journal of Computational Chemistry, vol. 32, pp. 582–599, 2011. View at Publisher · View at Google Scholar
  11. R. Carbó-Dorca and X. Gironés, “Foundation of quantum similarity measures and their relationship to QSPR: density function structure, approximations, and application examples,” International Journal of Quantum Chemistry, vol. 101, no. 8, p. 20, 2005. View at Publisher · View at Google Scholar
  12. R. Carbó-Dorca and X. Gironés, “Foundation of quantum similarity measures and their relationship to QSPR: density function structure, approximations, and application examples,” International Journal of Quantum Chemistry, vol. 101, no. 1, pp. 8–20, 2005. View at Publisher · View at Google Scholar · View at Scopus
  13. L. Amatand and R. Carbó-Dorca, “Use of promolecular ASA density functions as a general algorithm to obtain starting MO in SCF calculations,” International Journal of Quantum Chemistry, vol. 87, pp. 59–67, 2002. View at Publisher · View at Google Scholar
  14. R. Carbó-Dorca and E. Besalú, “Communications on quantum similarity (2): a geometric discussion on holographic electron density theorem and confined quantum similarity measures,” Journal of Computational Chemistry, vol. 31, pp. 2452–2462, 2010. View at Publisher · View at Google Scholar
  15. R. Carbó-Dorca, M. Arnau, and L. Leyda, “How similar is a molecule to another? An electron density measure of similarity between two molecular structures,” International Journal of Quantum Chemistry, vol. 17, pp. 1185–1189, 1980. View at Publisher · View at Google Scholar
  16. P. Bultinck and R. J. Carbó-Dorca, “Molecular quantum similarity using conceptual DFT descriptors,” Journal of Chemical Sciences, vol. 117, pp. 425–435, 2005. View at Publisher · View at Google Scholar
  17. R. G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, New York, NY, USA, 1989.
  18. R. Vivas-Reyes, F. de Proft, P. Geerlings et al., “A DFT and HF quantum chemical study of the tin nanocluster [(RSn)12O14(OH)6]2+ and its interactions with anions and neutral nucleophiles: confrontation with experimental data,” New Journal of Chemistry, vol. 26, no. 9, pp. 1108–1117, 2002. View at Publisher · View at Google Scholar · View at Scopus
  19. R. Mejia-Urueta, F. Nuñez-Zarur, and R. Vivas-Reyes, “Density functional study on electronic structures and reactivity in carbazol-oxadiazole dyads used in organic light emitting diodes,” International Journal of Quantum Chemistry, vol. 112, pp. 2808–2815, 2012. View at Publisher · View at Google Scholar
  20. F. de Proft, R. Vivas-Reyes, M. Biesemans, R. Willem, J. M. L. Martin, and P. Geerlings, “Density functional study of the complexation reaction of Sn(CH3)3X (X = F, Cl, Br and I) with Halide Anions,” European Journal of Inorganic Chemistry, no. 20, pp. 3803–3810, 2003. View at Google Scholar · View at Scopus
  21. A. Morales-Bayuelo and R. J. Vivas-Reyes, “Topological model to quantify the global reactivity indexes as local in Diels-Alder reactions, using density function theory (DFT) and local quantum similarity (LQS),” Journal of Mathematical Chemistry, vol. 51, pp. 125–143, 2013. View at Publisher · View at Google Scholar
  22. A. Morales-Bayuelo and A. J. Vivas-Reyes, “Theoretical model for the polarization molecular and Hückel treatment of PhosphoCyclopentadiene in an external electric field: Hirschfeld study,” Journal of Mathematical Chemistry, vol. 51, pp. 1835–1852, 2013. View at Publisher · View at Google Scholar
  23. A. Morales-Bayuelo and R. Vivas-Reyes, “Topological model on the inductive effect in alkyl halides using local quantum similarity and reactivity descriptors in the density functional theory,” Journal Quantum Chemistry, vol. 2014, Article ID 850163, 12 pages, 2014. View at Publisher · View at Google Scholar
  24. M. V. Putz, “Density functionals of chemical bonding,” International Journal of Molecular Sciences, vol. 9, no. 6, pp. 1050–1095, 2008. View at Publisher · View at Google Scholar · View at Scopus
  25. M. V. Putz, “Markovian approach of the electron localization functions,” International Journal of Quantum Chemistry, vol. 105, pp. 1–10, 2005. View at Publisher · View at Google Scholar
  26. M. V. Putz, “Chemical action and chemical bonding,” Journal of Molecular Structure: THEOCHEM, vol. 900, no. 1–3, pp. 64–70, 2009. View at Publisher · View at Google Scholar · View at Scopus
  27. E. Matito and M. V. Putz, “New link between conceptual density functional theory and electron delocalization,” Journal of Physical Chemistry A, vol. 115, no. 45, pp. 12459–12462, 2011. View at Publisher · View at Google Scholar · View at Scopus
  28. G. Haskó, J. Linden, B. Cronstein, and P. Pacher, “Adenosine receptor signaling in the brain immune system,” Nature Reviews Drug Discovery, vol. 7, pp. 759–770, 2008. View at Publisher · View at Google Scholar
  29. A. Morales-Bayuelo, H. Ayazo, and R. Vivas-Reyes, “Three-dimensional quantitative structure-activity relationship CoMSIA/CoMFA and LeapFrog studies on novel series of bicyclo [4.1.0] heptanes derivatives as melanin-concentrating hormone receptor R1 antagonists,” European Journal of Medicinal Chemistry, vol. 45, no. 10, pp. 4509–4522, 2010. View at Publisher · View at Google Scholar · View at Scopus
  30. M. Ahumedo, A. Díaz, and R. Vivas-Reyes, “Theoretical and structural analysis of the active site of the transcriptional regulators LasR and TraR, using molecular docking methodology for identifying potential analogues of acyl homoserine lactones (AHLs) with anti-quorum sensing activity,” European Journal of Medicinal Chemistry, vol. 45, pp. 608–615, 2010. View at Publisher · View at Google Scholar
  31. X. Gironés and R. Carbó-Dorca, “TGSA-Flex: extending the capabilities of the Topo-Geometrical superposition algorithm to handle flexible molecules,” Journal of Computational Chemistry, vol. 25, pp. 153–159, 2003. View at Publisher · View at Google Scholar
  32. L. Chen, “Substructure and maximal common substructure searching,” in Computational Medicinal Chemistry for Drug Discovery, P. Bultinck, H. de Winter, W. Langenaeker, and J. P. Tollenaere, Eds., p. 483, Marcel Dekker, New York, NY, USA, 2003. View at Google Scholar
  33. M. J. Frisch, G. W. Trucks, H. B. Schlegel et al., GAUSSIAN 09, Revision A.02, Gaussian, Wallingford, UK, 2009.
  34. A. D. Becke, “Density-functional exchange-energy approximation with correct asymptotic behavior,” Physical Review A, vol. 38, p. 3098, 1988. View at Publisher · View at Google Scholar
  35. C. Lee, W. Yang, and R. G. Parr, “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,” Physical Review B, vol. 37, no. 2, pp. 785–789, 1988. View at Publisher · View at Google Scholar · View at Scopus
  36. W. J. Hehre, L. Radom, P. V. R. Schleyer, and J. A. Pople, Ab Initio Molecular Orbital Theory, John Wiley & Sons, New York, NY, USA, 1986.
  37. R. Bultinck, X. Girones, and R. Carbó-Dorca, “Molecular quantum similarity: theory and applications,” Reviews in Computational Chemistry, vol. 21, pp. 127–207, 2005. View at Google Scholar
  38. E. E. Hodgkin and W. G. Richards, “Molecular Similarity,” Chemische Berichte, vol. 24, p. 1141, 1988. View at Google Scholar
  39. F. L. Hirshfeld, “Bonded-atom fragments for describing molecular charge densities,” heoretica Chimica Acta, vol. 44, pp. 129–138, 1977. View at Publisher · View at Google Scholar
  40. F. de Proft, C. van Alsenoy, A. Peeters, W. Langenaeker, and P. Geerlings, “Atomic charges, dipole moments, and Fukui functions using the Hirshfeld partitioning of the electron density,” Journal of Computational Chemistry, vol. 23, no. 12, pp. 1198–1209, 2002. View at Publisher · View at Google Scholar · View at Scopus
  41. M. Randic, “Design of molecules with desired properties,” in Concepts and Applications of Molecular Similarity, M. A. Johnson and G. M. Maggiora, Eds., pp. 77–145, Wiley-Interscience, New York, NY, USA, 1990. View at Google Scholar
  42. G. Boon, C. van Alsenoy, F. de Proft, P. Bultinck, and P. Geerlings, “Molecular quantum similarity of enantiomers of amino acids: a case study,” Journal of Molecular Structure: THEOCHEM, vol. 727, no. 1–3, pp. 49–56, 2005. View at Publisher · View at Google Scholar · View at Scopus
  43. P. G. Mezey, “Molecular physics: an international journal at the interface between chemistry and physics,” Molecular Physics, vol. 96, pp. 169–178, 1999. View at Publisher · View at Google Scholar
  44. L. Amat and R. Carbó-Dorca, “Quantum similarity measures under atomic shell approximation: first order density fitting using elementary Jacobi rotations,” Journal of Computational Chemistry, vol. 18, pp. 2023–2039, 1997. View at Google Scholar
  45. R. G. Parr and W. T. Yang, “Density functional approach to the frontier-electron theory of chemical reactivity,” Journal of the American Chemical Society, vol. 106, pp. 4049–4050, 1984. View at Publisher · View at Google Scholar
  46. M. Putz, “Systematic formulations for electronegativity and hardness and their atomic scales within density functional softness theory,” International Journal of Quantum Chemistry, vol. 106, pp. 361–389, 2006. View at Publisher · View at Google Scholar
  47. P. Bultinck and R. Carbó-Dorca, “A mathematical discussion on density and shape functions, vector semispaces and related questions,” Journal of Mathematical Chemistry, vol. 36, pp. 191–200, 2004. View at Publisher · View at Google Scholar
  48. R. M. Dreizler, Gross EKU Density Functional Theory, Springer, Berlin, Germany, 1990.
  49. R. F. Nalewajski and R. G. Parr, “Legendre transforms and Maxwell relations in density functional theory,” The Journal of Chemical Physics, vol. 77, no. 1, pp. 399–407, 1982. View at Google Scholar · View at Scopus
  50. M. Randic and C. L. Wilkins, “Graph theoretical approach to recognition of structural similarity in molecules,” Journal of Chemical Information and Modeling, vol. 19, pp. 31–37, 1979. View at Publisher · View at Google Scholar
  51. R. G. Parr and R. G. Pearson, “Absolute hardness: companion parameter to absolute electronegativity,” Journal of the American Chemical Society, vol. 105, no. 26, pp. 7512–7516, 1983. View at Google Scholar · View at Scopus
  52. M. Berkowitz and R. G. Parr, “Molecular hardness and softness, local hardness and softness, hardness and softness kernels, and relations among these quantities,” The Journal of Chemical Physics, vol. 88, no. 4, pp. 2554–2557, 1988. View at Google Scholar · View at Scopus
  53. R. G. Parr and L. J. Bartolotti, “Some remarks on the density functional theory of few-electron systems,” Journal of Physical Chemistry, vol. 87, no. 15, pp. 2810–2815, 1983. View at Google Scholar · View at Scopus
  54. A. C. Good and W. G. Richards, “Rapid evaluation of shape similarity using Gaussian functions,” Journal of Chemical Information and Modeling, vol. 33, pp. 112–116, 1993. View at Publisher · View at Google Scholar
  55. M. Putz, “Semiclassical electronegativity and chemical hardness,” Journal of Theoretical and Computational Chemistry, vol. 6, p. 33, 2007. View at Publisher · View at Google Scholar
  56. R. F. W. Bader, Atoms in Molecules. A Quantum Theory, Oxford Science Publications/Clarendon Press, London, UK, 1990.
  57. P. Bultinck, S. Fias, C. van Alsenoy, P. W. Ayers, and R. Carbó-Dorca, “Critical thoughts on computing atom condensed Fukui functions,” Journal of Chemical Physics, vol. 127, no. 3, Article ID 034102, 2007. View at Publisher · View at Google Scholar · View at Scopus
  58. K. Fukui, “Role of frontier orbitals in chemical reactions,” Science, vol. 217, pp. 747–754, 1982. View at Publisher · View at Google Scholar
  59. W. Yang, R. G. Parr, and R. Pucci, “Electron density, Kohn-Sham frontier orbitals, and Fukui functions,” The Journal of Chemical Physics, vol. 81, no. 6, pp. 2862–2863, 1984. View at Google Scholar · View at Scopus