Microwaves in drug discovery and multi-step synthesis

Molecular Diversity

Volumn 7, Issue 2-4, 2003, Pages 273-280

  Alexandre, François René ^a   Domon, Lisianne ^a   Frère, Stéphane ^a   Testard, Alexandra ^a   Thiéry, Valérie ^a   Besson, Thierry ^a  

^a UNIVERSITÉ DE LA ROCHELLE   (France)

Author keywords

Heterocyclic chemistry; Large scale; Microwave chemistry

Indexed keywords

HETEROCYCLIC COMPOUND; SOLVENT;

CHEMICAL REACTION; DRUG SCREENING; DRUG SYNTHESIS; HEATING; MICROWAVE RADIATION; PRIORITY JOURNAL; REVIEW; SOLVATION;

CARBON; CHEMISTRY, ORGANIC; DRUG DESIGN; HEATING; MICROWAVES; MODELS, CHEMICAL; NITRILES; SOLVENTS; TEMPERATURE;

EID: 0347717649     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:MODI.0000006860.56083.2b     Document Type: Review

References (25)

1. For recent books: (a) Loupy, A. (ed.), Microwaves in Organic Synthesis, Wiley-VCH Verlag Gmbh & Co. KGaA, Weinhein, 2002.
2. (b) Hayes, B. L., Microwave Synthesis: Chemistry at the Speed of Light, CEM Publishing, Matthews (U.S.A.), 2002.
3. (a) Chabane, H., Lamazzi, C., Thiéry, V., Pierré, A., Léonce, S., Pfeiffer, B., Renard, P., Guillaumet, G. and Besson, T., Synthesis and cytotoxic evaluation of novel thiazolocarbazoles, Pan II, J. Enz. Inh. Med. Chem., 18 (2003) 167-174.
4. (b) Lamazzi, C., Chabane, H., Thiéry, V., Pierré, A., Léonce, S., Pfeiffer, B., Renard, P., Guillaumet, G. and Besson, T., Synthesis and cytotoxic evaluation of novel thiazolocarbazoles, J. Enz. Inh. Med. Chem., 17 (2002) 397-401.
5. (c) Chabane, H., Lamazzi, C., Thiéry, V., Guillaumet, G. and Besson, T., Synthesis of novel 2-cyanothiazolocarbazoles analogues of ellipticine, Tetrahedron Lett., 43 (2002) 2483-2486.
6. (d) Besson, T. and Guillard, J., Synthesis of novel dioxinobenzothiazole derivatives, Tetrahedron, 55 (1999) 5139-5144.
7. (e) Bénéteau, V., Besson, T., Guillard, J., Leonce, S. and Pfeiffer, B., Synthesis and in vitro antitumour evaluation of benzothiazole-2-carbonitrile derivatives, Eur. J. Med. Chem., 34 (1999) 1053-1060.
8. (a) Molinski T. F., Marine pyridoacridine alkaloids: structure and biological chemistry, Chem. Rev., 93 (1993) 1825-1838.
9. (b) Gunawardana, G. P., Kohmoto, S., Gunasekara, S. P., McConnel O. J. and Koehn F. E., Dercitin, a new biologically active acridine alkaloid from a deep water sponge marine sponge, Dercitus sp., J. Am. Chem. Soc., 110 (1988) 4856-4858.
10. (c) Gunawardana, G. P., Kohmoto S. and Burres, N. S., New cytotoxic acridine alkaloids from two deep water marine sponges of the family Pachastrellidae, Tetrahedron Lett., 30 (1989) 4359-4362.
11. Sengupta, S. K., 'Topoisomerase II Inhibitors', in W. O. Foye (ed.), Cancer Chemotherapeutic Agents, ACS Professional Reference Books, Washington DC, 1995, pp. 246-260.
12. (a) Bénéteau, V., Besson, T. and Rees, C. W., Rapid synthesis of 2-cyanobenzothiazoles from N-aryliminodithiazoles under microwave irradiation, Synth. Commun., 27 (1997) 2275-2280.
13. (b) English, R. F., Rakitin, O. A., Rees, C. W. and Vlasova, O. G., Conversion of imino-1,2,3-dithiazoles into 2-cyanobenzothiazoles, cyanoimidoyl chlorides and diatomic sulphur, J. Chem. Soc., Perkin Trans. 1, (1997) 201-205.
14. (c) Besson, T. and Rees, C. W., Some chemistry of 4,5-dichloro-1,2,3-dithiazolium chloride and its derivatives, J. Chem. Soc.; Perkin Trans. 1, (1995) 1659-1662.
15. (d) Appel, R., Janssen, H., Siray, M. and Knoch, F., Syntheses und reacktionen des 4,5-dichlor-1,2,3-dithiazolium chlorids, Chem. Ber., 118 (1985) 1632-1643.
16. Frère, S., Thiéry, V., Bailly, C. and Besson, T., Novel 6-substituted benzothiazol-2-yl indolo[1,2-c]quinazolines and benzimidazo[1,2-c]quinazolines, Tetrahedron, 59 (2003) 773-779.
17. (a) Besson, T., Dozias, M. J., Guillard, J., Jacquault, P., Legoy, M. D. and Rees, C. W., Microwave irradiation in the presence of solvent: expeditious routes to 4-alkoxyquinazoline-2-carbonitriles and thiocarbamates via N-arylimino-1,2,3-dithiazoles, Tetrahedron, 54 (1998) 6475-6484.
18. (b) Besson, T., Dozias, M. J., Guillard, J. and Rees, C. W., New route to 2-cyanobenzothiazoles via N-arylimino-1,2,3-dithiazoles, J. Chem. Soc., Perkin Trans. 1, (1998) 3925-3926.
19. Von Niementowski, S., Synthesen von chinazolinverbindungen, J. Prakt. Chem., 51 (1895) 564-572.
20. Alexandre, F. R., Berecibar, A. and Besson, T., Microwave-assisted Niementowski reaction - Back to the roots, Tetrahedron Lett., 43 (2002) 3911-3913.
21. Laporterie, A., Marquié, J. and Dubac, J., 'Microwave-assisted Reactions on Graphite', in A. Loupy (ed.), Microwaves in Organic Synthesis, Whiley-VCH Verlag Gmbh & Co. KGaA, Weinhein, 2002, pp. 219-252.
22. Soukri, M., Guillaumet, G., Besson, T., Aziane, D., Aadil, M., Essassi, El. M. and Akssira, M., Synthesis of novel 5a,10,14b,15-tetraaza-benzo[a]indeno[1,2-c] anthracen-5-one and benzimidazo[1,2-c]quinazoline derivatives under microwave irradiation, Tetrahedron Lett., 41 (2000) 5857-5860.
23. Domon, L., Le Coeur, C., Grelard, A., Thiéry, V. and Besson, T., Efficient modified von Niementowski synthesis of novel derivatives of 5a,14b,15-triazabenzo[a]indeno[1,2c] anthracen-5-one from indolo[1,2-c]quinazoline, Tetrahedron Lett., 42 (2001) 6671-6674.
24. Besson, T., Guillard, J. and Rees, C. W., Multi-step synthesis of thiazoloquinazolines under microwave irradiation in solution, Tetrahedron Lett., 41 (2000) 1027-1030.
25. Alexandre, F. R., Berecibar, A., Wrigglesworth, R. and Besson, T., Efficient synthesis of thiazoloquinazolinone derivatives, Tetrahedron Lett., 44 (2003) 4455-4458.