Regioselective synthesis and molecular modeling study of vasorelaxant active 7,9-dioxa-1,2-diaza-spiro[4.5]dec-2-ene-6,10-diones

European Journal of Medicinal Chemistry

Volumn 45, Issue 9, 2010, Pages 4229-4238

  Girgis, Adel S ^a   Ismail, Nasser S M ^b   Farag, Hanaa ^a   El Eraky, Wafaa I ^a   Saleh, Dalia O ^a   Tala, Srinivasa R ^c   Katritzky, Alan R ^c  

^a NATIONAL RESEARCH CENTRE   (Egypt)

^b Ain Shams University   (Egypt)

^c UNIVERSITY OF FLORIDA   (United States)

Author keywords

5 Arylidene 2,2 dimethyl 1,3 dioxane 4,6 diones; 7,9 Dioxa 1,2 diaza spiro 4.5 dec 2 ene 6,10 diones; Dipolar cycloaddition; Hydrazonoyl halides; Molecular modeling; Vasodilation

Indexed keywords

1 (3 CHLOROPHENYL) 4 (4 CHLOROPHENYL) 8,8 DIMETHYL 3 PHENYL 7,9 DIOXA 1,2 DIAZA SPIRO[4.5]DEC 2 ENE 6,10 DIONE; 1 (3 CHLOROPHENYL) 8,8 DIMETHYL 3 PHENYL 4 (2 THIENYL) 7,9 DIOXA 1,2 DIAZA SPIRO[4.5]DEC 2 ENE 6,10 DIONE; 1 (3 CHLOROPHENYL) 8,8 DIMETHYL 4 (4 DIMETHYLAMINOPHENYL) 3 PHENYL 7,9 DIOXA 1,2 DIAZA SPIRO[4.5]DEC2 ENE 6,10 DIONE; 1 (3 CHLOROPHENYL) 8,8 DIMETHYL 4 (4 FLUOROPHENYL) 3 PHENYL 7,9 DIOXA 1,2 DIAZA SPIRO[4.5]DEC 2 ENE 6,10 DIONE; 1 (3 CHLOROPHENYL) 8,8 DIMETHYL 4 (4 METHOXYPHENYL) 3 PHENYL 7,9 DIOXA 1,2 DIAZA SPIRO[4.5]DEC 2 ENE 6,10 DIONE; 1 (3 CHLOROPHENYL) 8,8 DIMETHYL 4 (5 METHYL 2 FURANYL) 3 PHENYL 7,9 DIOXA 1,2 DIAZA SPIRO[4.5]DEC 2 ENE 6,10 DIONE; 4 (4 CHLOROPHENYL) 8,8 DIMETHYL 1,3 DIPHENYL 7,9 DIOXA 1,2 DIAZA SPIRO[4.5]DEC 2 ENE 6,10 DIONE; 7,9 DIOXA 1,2 DIAZA SPIRO[4.5]DEC 2 ENE 6,10 DIONE; 8,8 DIMETHYL 1,3 DIPHENYL 4 (2 THIENYL) 7,9 DIOXA 1,2 DIAZA SPIRO[4.5]DEC 2 ENE 6,10 DIONE; 8,8 DIMETHYL 1,3 DIPHENYL 4 (4 FLUOROPHENYL) 7,9 DIOXA 1,2 DIAZA SPIRO[4.5]DEC 2 ENE 6,10 DIONE; 8,8 DIMETHYL 1,3 DIPHENYL 4 (4 METHOXYPHENYL) 7,9 DIOXA 1,2 DIAZA SPIRO[4.5]DEC 2 ENE 6,10 DIONE; 8,8 DIMETHYL 1,3 DIPHENYL 4 (5 METHYL 2 FURANYL) 7,9 DIOXA 1,2 DIAZA SPIRO[4.5]DEC 2 ENE 6,10 DIONE; 8,8 DIMETHYL 4 (4 DIMETHYLAMINOPHENYL) 1,3 DIPHENYL 7,9 DIOXA 1,2 DIAZA SPIRO[4.5]DEC 2 ENE 6,10 DIONE; ALPHA 1 ADRENERGIC RECEPTOR BLOCKING AGENT; NORADRENALIN; UNCLASSIFIED DRUG; VASODILATOR AGENT;

ANIMAL TISSUE; ARTICLE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; GENETIC MODEL; HEART CONTRACTION; IN VITRO STUDY; MALE; NONHUMAN; RAT; VASCULAR RING; VASODILATATION; WISTAR RAT;

ADRENERGIC ALPHA-1 RECEPTOR ANTAGONISTS; ANIMALS; AORTA; MALE; MODELS, MOLECULAR; PROTEIN CONFORMATION; RATS; RATS, WISTAR; RECEPTORS, ADRENERGIC, ALPHA-1; SPIRO COMPOUNDS; STEREOISOMERISM; SUBSTRATE SPECIFICITY; VASODILATION; VASODILATOR AGENTS;

EID: 77955551434     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.06.018     Document Type: Article

References (32)

1. A.D. Lopez, C.D. Mathers, M. Ezzati, D.T. Jamison, and C.L. Murray Lancet 367 2006 1747 1757
2. K. Kulig, J. Sapa, A. Nowaczyk, B. Filipek, and B. Malawska Eur. J. Med. Chem. 44 2009 3994 4003
3. J. Liu, H. Ren, J. Xu, R. Bai, Q. Yan, W. Huang, X. Wu, J. Fu, Q. Wang, Q. Wu, and R. Fu Bioorg. Med. Chem. Lett. 19 2009 1822 1824
4. H. Marona, N. Szkaradek, A. Rapacz, B. Filipek, M. Dybała, A. Siwek, M. Cegła, and E. Szneler Bioorg. Med. Chem. 17 2009 1345 1352
5. A.S. Girgis, N. Mishriky, A.M. Farag, W.I. El-Eraky, and H. Farag Eur. J. Med. Chem. 43 2008 1818 1827
6. A.S. Girgis, A. Kalmouch, and M. Ellithey Bioorg. Med. Chem. 14 2006 8488 8494
7. S.-S. Hong, S.A. Bavadekar, S.-I. Lee, P.N. Patil, S.G. Lalchandani, D.R. Feller, and D.D. Miller Bioorg. Med. Chem. Lett. 15 2005 4691 4695
8. K.S. Jain, J.B. Bariwal, M.K. Kathiravan, M.S. Phoujdar, R.S. Sahne, B.S. Chauhan, A.K. Shah, and M.R. Yadav Bioorg. Med. Chem. 16 2008 4759 4800
9. T. Koshimizu, A. Tanoue, A. Hirasawa, J. Yamauchi, and G. Tsujimoto Pharmacol. Ther. 98 2003 235 244
10. M.A. Patane, A.L. Scott, T.P. Broten, R.S.L. Chang, R.W. Ranson, J. DiSalvo, C. Forray, and M.G. Bock J. Med. Chem. 41 1998 1206 1208
11. C.R. Chapple BJU Int. 94 2004 738 744
12. G. Chiu, S. Li, P.J. Connolly, V. Pulito, J. Liu, and S.A. Middleton Bioorg. Med. Chem. Lett. 18 2008 640 644
13. A.S. Girgis, Y.A. Ibrahim, I.S. Ahmed Farag, and N. Mishriky J. Chem. Res. (S) 2000 508 509
14. T. Fathi, K. Ciamala, N. Dinh An, and J. Vebrel Can. J. Chem. 72 1994 1424 1428
15. A.S. Girgis, F.F. Barsoum, and A. Samir Eur. J. Med. Chem. 44 2009 2447 2451
16. N. Mishriky, A.S. Girgis, H.M. Hosni, and H. Farag J. Heterocycl. Chem. 43 2006 1549 1556
17. A.S. Girgis J. Chem. Res. (S) 2006 81 83
18. A.S. Girgis, Y.A. Ibrahim, N. Mishriky, J.N. Lisgarten, B.S. Potter, and R.A. Palmer Tetrahedron 57 2001 2015 2019
19. J.M. Raimundo, R.T. Sudo, L.B. Pontes, F. Antunes, M.M. Trachez, and G. Zapata-Sudo Eur. J. Pharmacol. 530 2006 117 123
20. A.G. Silva, G. Zapata-Sudo, A.E. Kummerle, C.A.M. Fraga, E.J. Barreiro, and R.T. Sudo Bioorg. Med. Chem. 13 2005 3431 3437
21. J. Handzlik, D. Maciag, M. Kubacka, S. Mogilski, B. Filipek, K. Stadnicka, and K. Kieć-Kononowicz Bioorg. Med. Chem. 16 2008 5982 5998
22. I.J.A. MacDougall, and R. Griffith J. Mol. Graph. Model. 25 2006 146 157
23. M.A.H. Ismail, M.N.Y. Aboul-Enein, K.A.M. Abouzid, and R.A.T. Serya Bioorg. Med. Chem. 14 2006 898 910
24. R. Barbaro, L. Betti, M. Botta, F. Corelli, G. Giannaccini, L. Maccari, F. Manetti, G. Strappaghetti, and S. Corsano Bioorg. Med. Chem. 10 2002 361 369
25. N.S.M. Ismail, R. Salah El Dine, M. Hattori, K. Takahashi, and M. Ihara Bioorg. Med. Chem. 16 2008 7877 7887
26. O. Kaumanns, and H. Mayr J. Org. Chem. 73 2008 2738 2745
27. M. Chakrabarty, R. Mukherjee, M. Chakrabarty, S. Arima, and Y. Harigaya Lett. Org. Chem. 3 2006 868 871
28. F.J. Kunz, and O.E. Polansky Monatsh. Chem. 100 1969 920 927
29. F.J. Kunz, P. Margaretha, and O.E. Polansky Chimia 24 1970 165 181
30. G.D. Krapivin, V.G. Kul'nevich, and N.I. Val'ter Khim. Geterotsikl. Soedin. 1986 1325 1329 Chem. Abstr. 107 (1987) 77720
31. R. Huisgen, M. Seidel, G. Wallbillich, and H. Knupfer Tetrahedron 17 1962 3 29
32. A.F. Hegarty, J.A. Kearney, F.L. Scott, and J. Chem Soc. Perkin Trans. 2 1973 1422 1430