B3LYP/6-31G* conformational landscape in vacuo of some pterocarpan stereoisomers with biological activity

Physical Chemistry Chemical Physics

Volumn 6, Issue 10, 2004, Pages 2849-2857

  Alagona, Giuliano ^a   Ghio, Caterina ^a   Monti, Susanna ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; BITUCARPIN A; CARBON; CHROMAN DERIVATIVE; ERYBRAEDIN C; HYDROGEN; OXYGEN; PTEROCARPAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DENSITY FUNCTIONAL THEORY; DRUG CONFORMATION; DRUG STABILITY; DRUG STRUCTURE; FORCE; MATHEMATICAL COMPUTING; QUANTUM MECHANICS; ROTATION; SEPARATION TECHNIQUE; STEREOISOMERISM;

EID: 3042520767     PISSN: 14639076     EISSN: None     Source Type: Journal    
DOI: 10.1039/b315234k     Document Type: Article

References (58)

1. P. M. Dewick, "Isoflavonoids". In: The Flavonoids: Advances in Research since 1980, ed. J. B. Harborne, Chapman & Hall, London, 1988, pp. 125-204; P. M. Dewick, in: The Flavonoids: Advances in Research since 1986, ed. J. B. Harborne, Chapman & Hall, London, 1994, pp. 166-180.
2. P. M. Dewick, "Isoflavonoids". In: The Flavonoids: Advances in Research since 1980, ed. J. B. Harborne, Chapman & Hall, London, 1988, pp. 125-204; P. M. Dewick, in: The Flavonoids: Advances in Research since 1986, ed. J. B. Harborne, Chapman & Hall, London, 1994, pp. 166-180.
3. P. M. Dewick and M. J. Steel, Phytochemistry, 1982, 21, 1599.
4. P. G. Latha, D. A. Evans, K. R. Panikkar and K. K. Jayavardhanan, Fitoterapia, 2000, 71, 223.
5. L. A. Mitscher, H. Telikepall, E. McGhee and D. M. Shankel, Mutat. Res., 1996, 350, 143.
6. S. R. Menon, V. K. Patel, L. A. Mitscher, P. Shih, S. P. Pillai and D. M. Shankel, J. Nat. Prod., 1999, 62, 102.
7. Y. M. Yang, J. W. Hyun, M. S. Sung, H. S. Chung, B. K. Kim, W. H. Paik, S. S. Kang and J. G. Park, Planta Med., 1996, 62, 353; P. G. Latha and K. R. Panikkar, Fitoterapia, 1998, 69, 451.
8. Y. M. Yang, J. W. Hyun, M. S. Sung, H. S. Chung, B. K. Kim, W. H. Paik, S. S. Kang and J. G. Park, Planta Med., 1996, 62, 353; P. G. Latha and K. R. Panikkar, Fitoterapia, 1998, 69, 451.
9. N. J. Sun, S. H. Woo, J. M. Cassady and R. M. Snapka, J. Nat. Prod., 1998, 61, 362.
10. P. G. Latha and K. R. Panikkar, J. Ethnopharmacol., 1999, 68, 295; L. M. Perry, Medicinal Plants of East and Southeast Asia: Attributed Properties and Uses, MIT Press, MA, 1980, p. 223.
11. P. G. Latha and K. R. Panikkar, J. Ethnopharmacol., 1999, 68, 295; L. M. Perry, Medicinal Plants of East and Southeast Asia: Attributed Properties and Uses, MIT Press, MA, 1980, p. 223.
12. G. A. Lane, O. R. W. Sutherland and A. R. Skipp, J. Chem. Ecol., 1987, 13, 771.
13. C. R. Perrin and I. A. M. Cruickshank, Phytochemistry, 1969, 8, 971.
14. T. A. Engler, O. K. Lynch, J. P. Reddy and G. S. Gregory, Bioorg. Med. Chem. Lett., 1993, 3, 1229; T. A. Engler, K. O. LaTessa, R. Iynegar, W. Chai and K. Agrios, Bioorg. Med. Chem. Lett., 1996, 4, 1755.
15. T. A. Engler, O. K. Lynch, J. P. Reddy and G. S. Gregory, Bioorg. Med. Chem. Lett., 1993, 3, 1229; T. A. Engler, K. O. LaTessa, R. Iynegar, W. Chai and K. Agrios, Bioorg. Med. Chem. Lett., 1996, 4, 1755.
16. M. Nakagawa, K. Nakanishi, L. L. Darko and J. A. Vick, Tetrahedron Lett., 1982, 23, 3855.
17. L. Juhász, L. Szilágyi, S. Antus, J. Visy, F. Zsila and M. Simonyi, Tetrahedron, 2002, 58, 4261; L. Kiss, L. Szilágyi and S. Antus, Z. Naturforsch., 2002, 57b, 1165; L. Kiss, T. Kurtán, S. Antus and A. Bényei, Chirality, 2003, 15, 558; L. Kiss, T. Kurtán, S. Antus and H. Brunner, ARKIVOC 2003, http://www.arkat-usa.org/ark/journal/2003/Bernath/GB- 653J/GB-653J.pdf and refs. quoted therein.
18. L. Juhász, L. Szilágyi, S. Antus, J. Visy, F. Zsila and M. Simonyi, Tetrahedron, 2002, 58, 4261; L. Kiss, L. Szilágyi and S. Antus, Z. Naturforsch., 2002, 57b, 1165; L. Kiss, T. Kurtán, S. Antus and A. Bényei, Chirality, 2003, 15, 558; L. Kiss, T. Kurtán, S. Antus and H. Brunner, ARKIVOC 2003, http://www.arkat-usa.org/ark/journal/2003/Bernath/GB- 653J/GB-653J.pdf and refs. quoted therein.
19. L. Juhász, L. Szilágyi, S. Antus, J. Visy, F. Zsila and M. Simonyi, Tetrahedron, 2002, 58, 4261; L. Kiss, L. Szilágyi and S. Antus, Z. Naturforsch., 2002, 57b, 1165; L. Kiss, T. Kurtán, S. Antus and A. Bényei, Chirality, 2003, 15, 558; L. Kiss, T. Kurtán, S. Antus and H. Brunner, ARKIVOC 2003, http://www.arkat-usa.org/ark/journal/2003/Bernath/GB- 653J/GB-653J.pdf and refs. quoted therein.
20. L. Juhász, L. Szilágyi, S. Antus, J. Visy, F. Zsila and M. Simonyi, Tetrahedron, 2002, 58, 4261; L. Kiss, L. Szilágyi and S. Antus, Z. Naturforsch., 2002, 57b, 1165; L. Kiss, T. Kurtán, S. Antus and A. Bényei, Chirality, 2003, 15, 558; L. Kiss, T. Kurtán, S. Antus and H. Brunner, ARKIVOC 2003, http://www.arkat-usa.org/ark/journal/2003/Bernath/GB- 653J/GB-653J.pdf and refs. quoted therein.
21. L. Fenaroli, Flora Mediterranea, Giunti, Firenze, 1998, p. 236.
22. L. Pistelli, C. Noccioli, G. Appendino, F. Bianchi, O. Sterner and M. Ballero, Phytochemistry, 2003, 64, 595.
23. T. Maurich, In vitro Study of the Activity of two Novel Compounds Extracted from Psoralea bituminosa on Cancer Cell-Lines and Human Lymphocytes, 2002-2003 Thesis, University of Pisa.
24. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle and J. A. Pople, Gaussian 98 (Revision A.6), Gaussian, Inc., Pittsburgh, PA, 1998.
25. A. D. Becke, J. Chem. Phys., 1993, 98, 5648; C. Lee, W. Yang and R. G. Parr, Phys. Rev. B, 1988, 37, 785.
26. A. D. Becke, J. Chem. Phys., 1993, 98, 5648; C. Lee, W. Yang and R. G. Parr, Phys. Rev. B, 1988, 37, 785.
27. R. Ditchfield, W. J. Hehre and J. A. Pople, J. Chem. Phys., 1971, 54, 724; W. J. Hehre, R. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257; J. D. Dill and J. A. Pople, J. Chem. Phys., 1975, 62, 2921; P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 1973, 28, 213.
28. R. Ditchfield, W. J. Hehre and J. A. Pople, J. Chem. Phys., 1971, 54, 724; W. J. Hehre, R. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257; J. D. Dill and J. A. Pople, J. Chem. Phys., 1975, 62, 2921; P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 1973, 28, 213.
29. R. Ditchfield, W. J. Hehre and J. A. Pople, J. Chem. Phys., 1971, 54, 724; W. J. Hehre, R. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257; J. D. Dill and J. A. Pople, J. Chem. Phys., 1975, 62, 2921; P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 1973, 28, 213.
30. R. Ditchfield, W. J. Hehre and J. A. Pople, J. Chem. Phys., 1971, 54, 724; W. J. Hehre, R. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257; J. D. Dill and J. A. Pople, J. Chem. Phys., 1975, 62, 2921; P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 1973, 28, 213.
31. W. J. Hehre, R. F. Stewart and J. A. Pople, J. Chem. Phys., 1969, 51, 2657.
32. J. S. Binkley, J. A. Pople and W. J. Hehre, J. Am. Chem. Soc., 1980, 102, 939.
33. D. A. McQuarrie, Statistical Mechanics, University Science Books, Sausalito, CA, 2000.
34. D. A. Case, D. A. Pearlman, J. W. Caldwell, T. E. Cheatham III, J. Wang, W. S. Ross, C. L. Simmerling, T. A. Darden, K. M. Merz, R. V. Stanton, A. L. Cheng, J. J. Vincent, M. Crowley, V. Tsui, H. Gohlke, R. J. Radmer, Y. Duan, J. Pilera, I. Massova, G. L. Seibel, U. C. Singh, P. K. Weiner and P. A. Kollman, AMBER7, University of California, San Francisco, 2002.
35. C. I. Bayly, P. Cieplak, W. D. Cornell and P. A. Kollman, J. Phys. Chem., 1993, 97, 10 269.
36. T. A. Halgren, J. Comput. Chem., 1996, 17, 490; T. A. Halgren, J. Comput. Chem., 1996, 17, 520; T. A. Halgren, J. Comput. Chem., 1996, 17, 553; T. A. Halgren and R. B. Nachbar, J. Comput. Chem., 1996, 17, 587; T. A. Halgren, J. Comput. Chem., 1996, 17, 616.
37. T. A. Halgren, J. Comput. Chem., 1996, 17, 490; T. A. Halgren, J. Comput. Chem., 1996, 17, 520; T. A. Halgren, J. Comput. Chem., 1996, 17, 553; T. A. Halgren and R. B. Nachbar, J. Comput. Chem., 1996, 17, 587; T. A. Halgren, J. Comput. Chem., 1996, 17, 616.
38. T. A. Halgren, J. Comput. Chem., 1996, 17, 490; T. A. Halgren, J. Comput. Chem., 1996, 17, 520; T. A. Halgren, J. Comput. Chem., 1996, 17, 553; T. A. Halgren and R. B. Nachbar, J. Comput. Chem., 1996, 17, 587; T. A. Halgren, J. Comput. Chem., 1996, 17, 616.
39. T. A. Halgren, J. Comput. Chem., 1996, 17, 490; T. A. Halgren, J. Comput. Chem., 1996, 17, 520; T. A. Halgren, J. Comput. Chem., 1996, 17, 553; T. A. Halgren and R. B. Nachbar, J. Comput. Chem., 1996, 17, 587; T. A. Halgren, J. Comput. Chem., 1996, 17, 616.
40. T. A. Halgren, J. Comput. Chem., 1996, 17, 490; T. A. Halgren, J. Comput. Chem., 1996, 17, 520; T. A. Halgren, J. Comput. Chem., 1996, 17, 553; T. A. Halgren and R. B. Nachbar, J. Comput. Chem., 1996, 17, 587; T. A. Halgren, J. Comput. Chem., 1996, 17, 616.
41. J. Gasteiger and M. Marsili, Tetrahedron, 1980, 36, 3219; J. Gasteiger and H. Saller, Angew. Chem., Int. Ed. Engl., 1985, 24, 687; E. Hückel, Z. Phys., 1932, 76, 628.
42. J. Gasteiger and M. Marsili, Tetrahedron, 1980, 36, 3219; J. Gasteiger and H. Saller, Angew. Chem., Int. Ed. Engl., 1985, 24, 687; E. Hückel, Z. Phys., 1932, 76, 628.
43. J. Gasteiger and M. Marsili, Tetrahedron, 1980, 36, 3219; J. Gasteiger and H. Saller, Angew. Chem., Int. Ed. Engl., 1985, 24, 687; E. Hückel, Z. Phys., 1932, 76, 628.
44. SYBYL Molecular Modelling Software, Version 6.9 (Linux_os2), TRIPOS Associates, St. Louis, MO, April 2003.
45. K. G. R. Pachler and W. G. E. Underwood, Tetrahedron, 1967, 23, 1817.
46. S. Antus, T. Kurtán, L. Juhász, L. Kiss, M. Hollósi and Zs. Májer, Chirality, 2003, 15, 558.
47. G. Alagona and C. Ghio, Chem. Phys., 1996, 204, 239; P. I. Nagy, G. Alagona and C. Ghio, J. Am. Chem. Soc., 1999, 121, 4804.
48. G. Alagona and C. Ghio, Chem. Phys., 1996, 204, 239; P. I. Nagy, G. Alagona and C. Ghio, J. Am. Chem. Soc., 1999, 121, 4804.
49. G. Alagona and C. Ghio, Int. J. Quantum Chem., 2002, 90, 641; P. I. Nagy, G. Alagona, C. Ghio and K. Takács-Novák, J. Am. Chem. Soc., 2003, 125, 2770.
50. G. Alagona and C. Ghio, Int. J. Quantum Chem., 2002, 90, 641; P. I. Nagy, G. Alagona, C. Ghio and K. Takács-Novák, J. Am. Chem. Soc., 2003, 125, 2770.
51. R. J. Graham, R. T. Kroemer, M. Mons, E. G. Robertson, L. Snoek and J. P. Simons, J. Phys. Chem. A, 1999, 103, 9706.
52. P. Butz, R. T. Kroemer, N. A. Macleod and J. P. Simons, J. Phys. Chem. A, 2001, 105, 544.
53. J. A. Dickinson, M. R. Hockridge, R. T. Kroemer, E. G. Robertson, J. P. Simons, J. McCombie and M. Walker, J. Am. Chem. Soc., 1998, 120, 2622.
54. I. Unamuno, J. A. Fernández, A. Longarte and F. Castaño, J. Phys. Chem. A, 2001, 105, 11 524.
55. J. R. Carney and T. S. Zwier, Chem. Phys. Lett., 2001, 341, 77.
56. J. R. Carney and T. S. Zwier, J. Phys. Chem. A, 2000, 104, 8677.
57. A. Schöning and W. Friedrichsen, Z. Naturforsch. B, 1989, 44, 975.
58. G. Alagona and C. Ghio, work in progress.