Structure and atropisomerisation of new diastereomeric gossypol Schiff bases with (R)-(+)-2-amino-3-benzyloxy-1-propanol studied by NMR, ECD and DFT methods

Tetrahedron Asymmetry

Volumn 21, Issue 8, 2010, Pages 973-981

  Przybylski, Piotr ^a   Kwit, Marcin ^a   Pyta, Krystian ^a   Pankiewicz, Radosław ^a   Schroeder, Grzegorz ^a   Gawroński, Jacek ^a   Brzezinski, Bogumil ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 3 BENZYLOXY 1 PROPANOL; GOSSYPOL; PROPANOL; SCHIFF BASE; UNCLASSIFIED DRUG;

ARTICLE; ATROPISOMERISATION; CALCULATION; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; CONTROLLED STUDY; DIASTEREOISOMER; DISCRETE FOURIER TRANSFORM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; ISOMERIZATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SPECTROSCOPY; STEREOMETRY; SUNLIGHT; ULTRAVIOLET RADIATION;

EID: 77954314995     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.05.034     Document Type: Article

References (73)

1. R. Baksha, G.T. Mavlanov, G.B. Nasirova, and S.A. Djataev J. Biol. Sci. 6 2006 1126 1129
2. J. Wei, M.F. Rega, S. Kitada, H. Yuan, D. Zhai, P. Risbood, H.H. Seltzman, C.E. Twine, J.C. Reed, and M. Pellecchia Cancer Lett. 273 2009 107 113
3. V. Razakantoanina, N.K.P. Phung, and G. Jaureguiberry Parasit. Res. 86 2000 665 668
4. A.N. Narovlianskii, P.G. Deriabin, M.I. Vershinina, M.V. Mezentseva, and F.I. Ershov Vopr. Virusol. 47 2002 17 21
5. S. Boonsri, C. Karalai, C. Ponglimanont, S. Chantrapromma, and A. Kanjana-opas J. Nat. Prod. 71 2008 1173 1177
6. M.E. Mace, R.D. Stipanovic, and A.A. Bell Nat. Toxins 1 1993 294 295
7. P. Kovaci Curr. Med. Chem. 10 2003 2711 2718
8. K.R. Gawai, C. Cox, J. Jackson, and R.R. Dalvi Pharmacol. Toxicol. 76 1995 289 291
9. C. Van Ypersele de Strihou, J.P. Dieu, and E. Marbaix Contraception 37 1988 173 177
10. J. Kenar J. Am. Oil Chem. Soc. 83 2006 269 302
11. P. Przybylski, A. Huczyński, K. Pyta, B. Brzezinski, and F. Bartl Curr. Org. Chem. 13 2009 124 148
12. J.W. Jaroszewski, T. Strom-Hansen, and L.L. Hansen Chirality 4 1992 216 221
13. P. Przybylski, W. Schilf, B. Kamienski, B. Brzezinski, and F. Bartl Magn. Res. Chem. 46 2008 534 544
14. K.Zh. Rezhepov, Kh.L. Ziyaev, N.I. Baram, F.G. Kamaev, M.G. Levkovich, A.M. Saiitkulov, and A.I. Ismailov Chem. Nat. Compd. 39 2003 358 361
15. K.Z. Tilyabaev, S.A. Talipov, B.T. Ibragimov, M.K. Dowd, and A.M. Yuldashev J. Chem. Crystallogr. 39 2009 677 682
16. J.A. Bauer, B. Kumar, K.G. Cordell, M.E. Prince, H.H. Tran, G.T. Wolf, D.B. Chepeha, T.N. Teknos, S. Wang, A. Eisbruch, C.I. Tsien, S.G. Urba, F.P. Worden, J. Lee, K.A. Griffith, J.M.G. Taylor, N. D'Silva, S.J. Wang, K.G. Wolter, B. Henson, S.G. Fisher, T.E. Carey, and C.R. Bradford Int. J. Rad. Oncol. Biol. Phys. 69 2007 S106 S108
17. V.-T. Dao, M.K. Dowd, C. Gaspard, M.-T. Martin, J. Hémez, O. Laprévote, M. Mayer, and R.J. Michelot Bioorg. Med. Chem. 11 2003 2001 2006
18. V.-T. Dao, M.K. Dowd, M.-T. Martin, C. Gaspard, M. Mayer, and R.J. Michelot Eur. J. Med. Chem. 39 2004 619 624
19. K. Dodou, R.J. Anderson, W.J. Lough, D.A.P. Small, M.D. Shelley, and P.W. Groundwater Bioorg. Med. Chem. 13 2005 4228 4237
20. L. Zhang, H. Jiang, X. Cao, H. Zhao, F. Wang, Y. Cui, and B. Jiang Eur. J. Med. Chem. 44 2009 3961 3972
21. P. Przybylski, K. Pyta, D. Remlein-Starosta, G. Schroeder, B. Brzezinski, and F. Bartl Bioorg. Med. Chem. Lett. 19 2009 1996 2000
22. P. Przybylski, K. Pyta, J. Stefańska, M. Ratajczak-Sitarz, A. Katrusiak, A. Huczyński, and B. Brzezinski Eur. J. Med. Chem. 44 2009 4393 4403
23. P. Przybylski, J. Kira, G. Schroeder, B. Brzezinski, and F. Bartl J. Phys. Chem. A 112 2008 8061 8069
24. S.A. Matlin, and R. Zhou J. High Resolut. Chromatogr. Chromatogr. Commun. 7 1984 629 631
25. M.K. Dowd Chirality 15 2003 486 493
26. H.-X. Jiang, X.-X. Cao, H. Huang, and B. Jiang Tetrahedron: Asymmetry 18 2007 2437 2441
27. R.G. Fish, P.W. Groundwater, and J.J. Gwynfor Morgan Tetrahedron: Asymmetry 6 1995 873 876
28. P. Przybylski, and B. Brzezinski Biopolymers: Biospectroscopy 67 2002 61 69
29. D.A. Lightner, and J.E. Gurst Organic Conformational Analysis and Stereochemistry From Circular Dichroism Spectroscopy 2000 Wiley-VCH New York
30. N. Berova, K. Nakanishi, R.W. Woody, Circular Dichroism 2nd ed. Principles and Applications 2000 Wiley-VCH New York
31. G. Snatzke Angew. Chem., Int. Ed. Engl. 18 1979 363 377
32. J.A. Schellman Chem. Rev. 75 1975 323
33. A. Moscowitz Tetrahedron 13 1961 48 56
34. Pecul, M.; Ruud, K. The Ab Initio Calculation of Optical Rotation and Electronic Circular Dichroism in Advances in Quantum Chemistry, Response, Theory and Molecular Properties, Elsevier, 2005, 50, pp 185-212
35. T.D. Crawford, M.C. Tam, and M.L. Abrams J. Phys. Chem. A 111 2007 12057 12068
36. D.T. Crawford Theor. Chem. Acc. 115 2006 227 245
37. F. Neese Coord. Chem. Rev. 253 2009 526 563
38. See for example: B.L. Feringa, Molecular Switches 2001 Wiley-VCH Weinheim
39. B.L. Feringa, R.A. van Delden, N. Koumura, and E.M. Geertsema Chem. Rev. 100 2000 1789 1816
40. M.K.J. ter Wiel, R.A. van Delden, A. Meetsma, and B.L. Feringa J. Am. Chem. Soc. 125 2003 15076 15086
41. M.K.J. ter Wiel, M.G. Kwit, A. Meetsma, and B.L. Feringa Org. Biomol. Chem. 5 2007 87 96
42. G. Caroli, M.G. Kwit, and B.L. Feringa Tetrahedron 64 2008 5956 5962
43. W. Bicker, K. Kacprzak, M. Kwit, M. Lämmerhofer, J. Gawronski, and W. Lindner Tetrahedron: Asymmetry 20 2009 1027 1035
44. P. Chochrek, J. Frelek, M. Kwit, and J. Wicha J. Org. Chem. 74 2009 7300 7308
45. M. Kwit, M.D. Rozwadowska, J. Gawronski, and A. Grajewska J. Org. Chem. 74 2009 8051 8063
46. J. Gawronski, M. Kwit, D.R. Boyd, N.D. Sharma, J.F. Malone, and A.F. Drake J. Am. Chem. Soc. 127 2005 4308 4319
47. S. Grimme J. Chem. Phys. 124 2006 034108
48. S. Grimme, and F. Neese J. Chem. Phys. 127 2007 154116
49. J. Gawronski, M. Kwit, and P. Skowronek Org. Biomol. Chem. 7 2009 1562 1572
50. M. Kwit, J. Gawronski, D.R. Boyd, N.D. Sharma, M. Kaik, R. More O'Ferrall, and J.S. Kudavalli Chem. Eur. J. 14 2008 11500 11511
51. R. Cysewski, M. Kwit, B. Warajtis, U. Rychlewska, and J. Gawroński J. Org. Chem. 74 2009 4573 4583
52. N. Harada, and K. Nakanishi Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry 1983 Mill Valley, CA Mill Valley, CA
53. J. Gawroński, and P. Skowronek Curr. Org. Chem. 8 2004 65 82
54. L. Huang, Y.-K. Si, G. Snatzke, D.K. Zheng, and J. Zhou Coll. Czech. Chem. Commun. 53 1988 2664
55. T.B. Freedman, X. Cao, R.V. Oliveira, Q.B. Cass, and L.A. Nafie Chirality 15 2003 196 200
56. P. Przybylski, G. Schroeder, and B. Brzezinski Phys. Chem. Chem. Phys. 4 2002 6137 6143
57. P. Przybylski, G. Bejcar, W. Schilf, B. Kamieński, and B. Brzezinski J. Mol. Struct. 826 2007 150 155
58. E.N. Da Silva Jr., M.C.B.V. De Souza, A.V. Pinto, M.D.C.F.R. Pinto, C.M. Nogueira, V.F. Ferreira, and R.B.V. Azeredo Magn. Res. Chem. 46 2008 1158 1162
59. A.K.L. Santos, J.C. Assunão, A.M. Fonseca, O.D.L. Pessoa, F.J.Q. Monte, T.L.G. Lemos, and R. Braz-Filho Magn. Res. Chem. 43 2005 582 584
60. L. Sobczyk, S.J. Grabowski, and T.M. Krygowski Chem. Rev. 105 2005 3513 3560
61. A. Filarowski, A. Koll, and L. Sobczyk Curr. Org. Chem. 13 2009 172 193
62. P. Sanz, O. Mo, M. Yañez, and J. Elguero J. Phys. Chem. A 111 2007 3585 3591
63. I. Alkorta, J. Elguero, O. Mo, M. Yañez, and J.E.D. Bene Chem. Physc. Lett. 411 2005 411 415
64. P. Przybylski, G. Bejcar, A. Huczyński, G. Schroeder, B. Brzezinski, and F. Bartl Biopolymers 82 2006 521 535
65. M. Kwit, and J. Gawroński Tetrahedron: Asymmetry 14 2003 1303 1308
66. I. Warnke, S. Ay, S. Bräse, and F.J. Furche Phys. Chem. A 113 2009 6987 6993
67. CAChe WS Pro 4.5, Fujitsu Ltd.
68. gaussian 03, Revision C.02, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Wallingford CT, 2004.
69. R. Ahlrichs, M. Bär, M. Häser, H. Horn, and C. Kölmel Chem. Phys. Lett. 162 1989 165 169 see also: www.turbomole-gmbh.com for overview of the turbomole program
70. Y.-K. Si, D.K. Zheng, and L. Huang Acta Pharm. Sin. 25 1990 423
71. P.J. Stephens, D.M. McCann, E. Butkus, S. Stonius, J.R. Cheeseman, and M.J. Frisch J. Org. Chem. 69 2004 1948 1958
72. P.J. Stephens, F.J. Devlin, J.R. Cheeseman, M.J. Frisch, O. Bortolini, and P. Besse Chirality 15 2003 S57
73. M. Kwit, N.D. Sharma, D.R. Boyd, and J. Gawronski Chem. Eur. J. 13 2007 5812 5821