Intramolecular approach to some new D-ring-fused steroidal isoxazolidines by 1,3-dipolar cycloaddition: Synthesis, theoretical and in vitro pharmacological studies

New Journal of Chemistry

Volumn 34, Issue 11, 2010, Pages 2671-2681

  Frank, Éva ^a   Mucsi, Zoltán ^a   Szécsi, Mihály ^a   Zupkó, István ^a   Wölfling, János ^a   Schneider, Gyula ^a  

^a UNIVERSITY OF SZEGED   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

3BETA ACETOXY 16,17 SECOPREGNA 5,17(20) DIEN 16 AL; 3BETA HYDROXY 2' BENZYL 5' METHYLISOXAZOLIDINO[4',5':17:16]ANDROST 5 ENE; 3BETA HYDROXY 2' CYCLOHEXYL 5' METHYLISOXAZOLIDINO[4',5':17:16]ANDROST 5 ENE; 3BETA HYDROXY 2' ISOPROPYL 5' METHYLISOXAZOLIDINO[4',5':17:16]ANDROST 5 ENE; 3BETA HYDROXY 2',5' DIMETHYLISOXAZOLIDINO[4',5':17:16]ANDROST 5 ENE; 3BETA HYDROXY 5' METHYLISOXAZOLIDINO[3',4':16,17]ANDROST 5 ENE; ALDEHYDE DERIVATIVE; ALKENYL GROUP; HYDROXYLAMINE; ISOXAZOLIDINE DERIVATIVE; NITRONE DERIVATIVE; OXIME DERIVATIVE; SECOPREGNENE ALDEHYDE; STEROID 17,20 LYASE; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CATALYST; CELL STRAIN MCF 7; CHEMICAL REACTION; CONTROLLED STUDY; CYCLIZATION; CYCLOADDITION; CYTOPATHOGENIC EFFECT; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ASSAY; ENZYME INHIBITION; HELA CELL; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; REPRODUCIBILITY; STEREOCHEMISTRY; TECHNIQUE; THERMAL STIMULATION;

EID: 78049306126     PISSN: 11440546     EISSN: 13699261     Source Type: Journal    
DOI: 10.1039/c0nj00150c     Document Type: Article

References (49)

1. J. J. Tufariello, in 1,3-Dipolar cycloaddition chemistry, ed., A. Padwa, J. Wiley & Sons Inc., New York, 1984, pp. 83-168
2. J. N. Martin and R. C. F. Jones, in Synthetic applications of 1,3-dipolar cycloaddition chemistry toward heterocycles and natural products, ed., A. Padwa, W. H. Pearson, J. Wiley & Sons Inc., Hoboken, New Jersey, 2003, pp. 1-81
3. K. V. Gothelf K. A. Jørgensen Chem. Rev. 1998 98 863 909
4. V. Nair T. D. Suja Tetrahedron 2007 63 12247 12275
5. A. Padwa, in 1,3-Dipolar cycloaddition chemistry, ed., A. Padwa, J. Wiley & Sons Inc., New York, 1984, pp. 279-304.
6. M. Frederickson Tetrahedron 1997 53 403 425
7. P. Merino T. Tejero M. Laguna E. Cerrada A. Moreno J. A. Lopez Org. Biomol. Chem. 2003 1 2336 2342
8. D. Carmona M. P. Lamata F. Viguri R. Rodríguez L. A. Oro A. I. Balana F. J. Lahoz T. Tejero P. Merino S. Franco I. Montesa J. Am. Chem. Soc. 2004 126 2716 2717
9. L. R. Domingo W. Benchouk S. M. Mekelleche Tetrahedron 2007 63 4464 4471
10. H. Pellissier Tetrahedron 2007 63 3235 3285
11. T. Kano T. Hashimoto K. Maruoka J. Am. Chem. Soc. 2005 127 11926 11927
12. S. Minakata T. Ezoe K. Nakamura I. Ryu M. Komatsu Tetrahedron Lett. 1998 39 5205 5208
13. P. Pérez L. R. Domingo M. J. Aurell R. Contreras Tetrahedron 2003 59 3117 3125
14. R. Grigg F. Heaney J. Markandu S. Surendrakumar M. Thorton-Pett W. J. Warnock Tetrahedron 1991 47 4007 4030
15. A. Padwa S. K. Bur Tetrahedron 2007 63 5341 5378
16. A. Padwa U. Chiacchio D. C. Dean A. M. Schoffstall A. Hassner K. S. K. Murthy Tetrahedron Lett. 1988 29 4169 4172
17. É. Frank J. Wölfling B. Aukszi V. König T. R. Schneider Gy. Schneider Tetrahedron 2002 58 6843 6849
18. Y. Wu G.-F. Dai J.-H. Yang Y.-X. Zhang Y. Zhu J.-C. Tao Bioorg. Med. Chem. Lett. 2009 19 1818 1821
19. J. Tanaka S. Kanemasa Tetrahedron 2001 57 899 905
20. L. F. de Oliveira V. E. U. Costa Tetrahedron: Asymmetry 2004 15 2583 2590
21. H. Singh D. P. Jindal M. R. Yadav M. Kumar Prog. Med. Chem. 1991 28 233 300
22. L. F. Tietze Gy. Schneider J. Wölfling A. Fecher T. Nöbel S. Petersen I. Schuberth C. Wulff Chem.-Eur. J. 2000 6 3755 3760
23. L. B. Lorenc I. O. Juranić M. M. Dabović M. Lj. Mihailović Tetrahedron 1991 47 6389 6398
24. R. K. Varma, N. J. Belle Mead, C. M. Cimarusti and N. J. Hamilton, US Pat., 4 018 774, Elsevier, Newyork, 1977
25. S. Colombi G. Vecchio G. Gottarelli B. Samori A. M. Manotti Lanfredi A. Tiripicchio Tetrahedron 1978 34 2967 2976
26. Ch. Camoutsis S. Nikolaropoulos J. Heterocycl. Chem. 1998 35 731 759
27. M. Lj. Mihailović M. M. Rajković L. B. Lorenc V. D. Pavlović A. Milovanović B. Tinant J.-P. Declercq Tetrahedron 1996 52 11995 12008
28. J. Wölfling A. Magyar Gy. Schneider Monatsh. Chem. 2003 134 1387 1393
29. É. Frank Zs. Kardos J. Wölfling Gy. Schneider Synlett 2007 1311 1313
30. P. Boontheung P. Perlmutter E. Puniani ARKIVOC 2001 viii 95 103
31. P. J. Dunn A. B. Graham R. Grigg P. Higginson I. S. Saba Chem. Commun. 2000 2033 2034
32. M. Noguchi H. Okada S. Nishimura Y. Yamagata S. Takamura M. Tanaka A. Kakehi H. Yamamoto J. Chem. Soc., Perkin Trans. 1 1999 185 191
33. B. S. Orlek P. G. Sammes D. J. Weller J. Chem. Soc., Chem. Commun. 1993 1412 1413
34. K. V. Gothelf and K. A. Jørgensen, in Synthetic applications of 1,3-dipolar cycloaddition chemistry toward heterocycles and natural products, ed., A. Padwa, and, W. H. Pearson, J. Wiley & Sons Inc., Hoboken, New Jersey, 2003, pp. 818-822
35. A. Hassner E. Falb A. Nudelman A. Albeck H. E. Gottlieb Tetrahedron Lett. 1994 35 2397 2400
36. T. P. Culbertson G. W. Moersch W. A. Neuklis J. Heterocycl. Chem. 1964 1 280 287
37. R. K. Varma and C. M. Cimarusti, US Pat., 4 018 774, 1977
38. M. J. Green R. L. Tiberi R. Friary B. N. Lutsky J. Berkenkoph X. Fernandez M. Monahan J. Med. Chem. 1982 25 1492 1495
39. A. E. E. Amr N. A. Abdel-Latif M. M. Abdalla Bioorg. Med. Chem. 2006 14 373 384
40. É. Frank Z. Mucsi I. Zupkó B. Réthy G. Falkay Gy. Schneider J. Wölfling J. Am. Chem. Soc. 2009 131 3894 3904
41. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr, 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, A. G. Baboul, 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, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle and J. Pople, A. Gaussian 03 6.0, Gaussian, Inc., Pittsburgh PA, 2003
42. A. D. Beke J. Chem. Phys. 1993 98 5648 5652
43. M. Head-Gordon J. A. Pople M. J. Frisch Chem. Phys. Lett. 1988 153 503 506
44. Z. Mucsi A. Szabó I. Hermecz Á. Kucsman I. Csizmadia J. Am. Chem. Soc. 2005 127 7615 7631
45. J. Wölfling E. A. Oravecz D. Ondré E. Mernyák Gy. Schneider I. Tóth M. Szécsi J. Julesz Steroids 2006 71 809 816
46. D. Ondré J. Wölfling Z. Iványi Gy. Schneider I. Tóth M. Szécsi J. Julesz Steroids 2008 73 1375 1384
47. T. Mossman J. Immunol. Methods 1983 65 55 63
48. P. Csomós I. Zupkó B. Réthy L. Fodor G. Falkay G. Bernáth Bioorg. Med. Chem. Lett. 2006 16 6273 6276
49. B. Réthy I. Zupkó R. Minorics J. Hohmann I. Ocsovszki G. Falkay Planta Med. 2007 73 41 48