Drug design of new antitubercular agents: 1,3-Dipolar cycloaddition reaction of para-substituted-benzadoximes and 3-para-methoxy-benzyliden- isochroman-4-ones

Arkivoc

Volumn 2008, Issue 12, 2008, Pages 42-50

  Al Houari, Ghali ^a   Kerbal, Abdelali ^a   Bennani, Brahim ^a   Baba, Mohamed F ^a   Daoudi, Maria ^a   Hadda, Taibi Ben ^b  

^a Sidi Mohamed Ben Abdellah University   (Morocco)

^b FACULTÉ DES SCIENCES   (Morocco)

Author keywords

1,3 dipolar cycloaddition; Pharmacophore site; Spiroisoxazoline; Tuberculosis

Indexed keywords

EID: 46249098207     PISSN: 1551-7012     EISSN: 15517012     Source Type: Journal    
DOI: 10.3998/ark.5550190.0009.c05     Document Type: Article

References (30)

1. Howe, R. K.; Shelton, B. R. J. Org. Chem. 1990, 4603.
2. Smietana, M.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 1291.
3. Bennani, B.; Kerbal, A.; Ben Larbi, N.; Ben Hadda, T.; Synthesis and application of spiro-isoxazolines as new anti-tubercular agents, OMPIC, Moroccan Patent No. 2769, 2004.
4. Bennani, B.; Kerbal, A.; Ben Larbi, N.; Ben Hadda, T. Synthesis and application of isothiochromeno[3,4-e][1,2]oxazine (TCO) as new antitumoral agents, OMPIC, Moroccan Patent No 2771, 2004.
5. Benchat, N.; El Bali, B.; Abouricha, S.; Moueqqit, M.; Mimouni, M.; Ben Hadda,T. Med. Pharm. Chem. 2003, 1.
6. Anaflous, A.; Benchat, N.; Mimouni, M.; Abouricha, S.; Ben Hadda, T.; El Bali, B.; Hakkou, A.; Hacht, B. Lett. Drug Des. Disc. 2004, 1, 35.
7. Tshiamala, K.; Kerbal, A.; Vebrel, J.; Laude, B. J. Chem. Res.(S) 1988, 3, 106.
8. Kerbal, A.; Vebrel, J.; Cerutti, E.; Laude, B. J. Chem. Soc.,Chem. Commun. 1989, 632.
9. Filali Baba, B.; Kerbal, A.; Bitit, N.; El Bali, B.; Escudie, J.; Ranaivonjatovo, H.; Bolte, M. Acta. Cryst. 2000, C56, 205.
10. Kerbal, A.; Tshiamala, K.; Vebrel, J.; Laude, B. Bull. Soc. Chim. Belg. 1988, 97, 149.
11. Kerbal, A.; Tshiamala, K.; Verbrel, J.; Laude B.; Mercier, M. F. Bull. Soc. Chim. Belg. 1991, 2, 159.
12. Theobala, F.; Rodier, N.; Kerbal, A.; Tshiamala, K.; Laude, B. Acta. Crys. 1990, C46, 1312.
13. Kerbal, A.; Vebrel, J.; Roche, M.; Laude, B. Tetrahedron Lett. 990, 31, 4145.
14. Badri, R.; Kerbal, A.; El Bali, B.; Escudie, B.; Ranaivonjatovo, H.; Bolte, M. Acta Cryst. 1999, C55.
15. Pivnenko, N. S.; Orlov, V. D.; Nodel'Man, O. A.; Mikhed'Kina, E. I.; Lavrushin, V.F. Zh. Org. Khim. 1980, 16, 1945.
16. Cacciarini, M.; Cordero, F. M.; Faggi, C.; Goti, A. Molecules 2000, 5, 637.
17. Chiacchio, U.; Casucelli, F.; Corsaro, A.; Rescifina, A.; Romeo, G.; Uccella, N. Tetrahedron 1994, 50, 6671.
18. Chritl, R.; Huisgen, M. Chem. Ber. 1973, 106, 345.
19. Jones, A. D.; Knight, D.; Thornton, S.R. J. Chem. Soc., Perkin Trans. 1 1999, 1, 337.
20. Fornefeld, E. J.; Pike, J. J. Org. Chem. 1979, 44, 835.
21. Asrof Ali, S.K.; Wazeer Mazhar-UI-Haque, M.I. Tetrahedron 1990, 46, 7207.
22. Chaner-Reny, J.; Chrmier-Junuario, M. O.; Vessière, R.; Zuccarelli, M. J. Heterocyclic Chem. 1997, 31, 1667.
23. Rastelli, A.; Gandolfi, R.; Amade, M. S.; Advances In Quantum Chemistry. 2000, 36,151.
24. Bennani, B.; Filali Baba, B.; EL-Fazazi, A.; Al Houari, G.; El Bali, B.; Bolte, M.; Ben Larbi, N.; Kerbal, A. J. Mar. Chim. Hétéroc. 2003, 1, 1.
25. Christl, M.; Huisgen, R.; Sustmann, R. Chem. Ber. 1973, 106, 3235, 1,3-Dipolar cycloaddition chemistry, A. Padwa, Wiley: New York, 337.
26. Chritl, M.; Huisgen, R. Chem. Ber. 1973, 106, 345.
27. Bast, K.; Christl, M.; Huisgen, R.; Mach, W. Chem. Ber.1973, 106, 3312.
28. Alami, A.; Soufiaoui, M. J. Soc. Mar. Chim. 1992, 1, 3589.
29. Ben Hadda, T.; Badri, R.; Kerbal, A.; Filali Baba, B.; Akkurt, M.; Demailly, G.; Benazza, M. Looking for a new antitubercular pharmacophore site: synthesis and bioactivity of spiroheterocycles 2,3′,4′-tri- subsituted-1,2-dihydro-4H,4′H-spiro[isoquinoline-3,5′-isoxazol] -4-ones. Manuscript submitted to Arkivoc.
30. Ben Hadda, T.; Badri, R.; Kerbal, A.; Filali Baba, B.; Akkurt, M.; Demailly, G.; Benazza, M. Arkivoc 2007, (xiv), 276.