Novel 6-substituted benzothiazol-2-yl indolo[1,2-c]quinazolines and benzimidazo[1,2-c]quinazolines

Tetrahedron

Volumn 59, Issue 6, 2003, Pages 773-779

  Frère, Stéphane ^a   Thiéry, Valérie ^a   Bailly, Christian ^b   Besson, Thierry ^a  

^a UNIVERSITÉ DE LA ROCHELLE   (France)

^b Institut de Recherche sur le Cancer de Lille   (France)

Author keywords

Benzimidazo 1,2 c quinazoline; Benzothiazoles; Indolo 1,2 c quinazoline; Microwave irradiation

Indexed keywords

DIAMINE; IMIDAZOLE DERIVATIVE; INDOLE DERIVATIVE; QUINAZOLINE DERIVATIVE; THIAZOLE DERIVATIVE;

ARTICLE; DRUG SCREENING; MICROWAVE RADIATION; POLYMERIZATION; PRIORITY JOURNAL;

EID: 0037415489     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01593-4     Document Type: Article

References (34)

1. (a) Molinski T.F. Chem. Rev. 93:1993;1825-1838
2. (b) Gunawardana G.P., Kohmoto S., Gunasekara S.P., McConnel O.J., Koehn F.E. J. Am. Chem. Soc. 110:1988;4856-4858
3. (c) Gunawardana G.P., Kohmoto S., Burres N.S. Tetrahedron Lett. 30:1989;4359-4362.
4. (a) Robin M., Faure R., Périchaud A., Galy J.P. Heterocycles. 53:2000;387-395
5. (b) Hanoun J.P., Faure R., Galy J.P., Elguero J. J. Heterocycl. Chem. 33:1996;747-750
6. (c) Barbe J., Boyer G., Carignano I., Elguero J., Galy J.P., Morel S., Oughedani R. Tetrahedron Lett. 32:1991;6709-6710.
7. Alvarez-Ibarra C., Fernandez-Granda R., Quiroga M.L., Carbonell A., Cardenas F., Giralt E. J. Med. Chem. 40:1997;668-676.
8. (a) Wells G., Bradshaw T.D., Diana P., Seaton A., Shi D.-F., Westwell A.D., Stevens M.F.G. Bioorg. Med. Chem. Lett. 10:2000;513-515
9. (b) Bradshaw T.D., Wrigley S., Shi D.-F., Schultz R.J., Paull K.D., Stevens M.F.G. Br. J. Cancer. 77:1998;745-752.
10. Besson T., Guillard J. Tetrahedron. 55:1999;5139-5144.
11. Bénéteau V., Besson T., Guillard J., Léonce S., Pfeiffer B. Eur. J. Med. Chem. 34:1999;1053-1060.
12. Besson T., Guillard J., Rees C.W. Tetrahedron Lett. 41:2000;1027-1030.
13. Lamazzi C., Chabane H., Thiéry V., Pierré A., Léonce S., Pfeiffer B., Renard P., Guillaumet G., Besson T. J. Enz. Inh. Med. Chem. 2002;. in press.
14. Chabane H., Lamazzi C., Thiéry V., Guillaumet G., Besson T. Tetrahedron Lett. 43:2002;2483-2486.
15. (a) Sengupta S.K., Cheng X.C.C. Foye W.O. Cancer Chemotherapeutic Agents. 1995;246-251 ACS Professional Reference Books, Washington, DC
16. (b) Moody C.J. Synlett. 1994;681-688
17. (c) Kansal V.K., Potier P. Tetrahedron. 42:1986;2389-2408
18. (d) Sainsbury M. Synthesis. 1977;437-448.
19. Appel R., Janssen H., Siray M., Knoch F. Chem. Ber. 118:1985;1632-1643.
20. (a) Bénéteau V., Besson T., Rees C.W. Synth. Commun. 27:1997;2275
21. (b) Bénéteau V., Besson T., Guillard J., Léonce S., Pfeiffer B. Eur. J. Med. Chem. 34:1999;1053
22. (c) Besson T., Rees C.W., Roe D.G., Thiéry V. J. Chem. Soc., Perkin Trans. 1. 2000;555-561.
23. (a) Helissey P., Cros S., Giorgi-Renault S. Anti-Cancer Drug Des. 9:1994;51-57
24. (b) Brana M.F., Castellano J.M., Keilhauer G., Machuca A., Martin Y., Redondo C., Schlick E., Walker N. Anti-Cancer Drug Des. 9:1994;527-538
25. (c) Riou J.F., Helissey P., Grondard L., Giorgi-Renault S. Mol. Pharmacol. 40:1991;699-706
26. (d) Ibrahim E., Montgomerie A.M., Sneddon A.H., Proctor G.R., Green B. Eur. J. Med. Chem. 23:1988;183-188.
27. (a) Billimmoria A.D., Cava M.P. J. Org. Chem. 59:1994;6777-6782
28. (b) . Hinckdentine A (1) as been isolated from the bryozoan Hincksinoflustra denticulata, collected off the eastern coast of Tasmania: Blackman A., Hambley T.W., Picker R., Taylor W.C., Thirasana N. Tetrahedron Lett. 28:1987;5561-5564.
29. Focused microwave irradiations were carried out at atmospheric pressure with a Synthewave S402 Prolabo microwave reactor (300 W, monomode system) which has quartz reactors, visual control, irradiation monitored by PC computer, infrared measurement and continuous feedback temperature control (by PC). Equipment of the oven can be completed by an external stirring system, a condenser and dropping funnel allowing conditions close to those involved in classical methods; it is also possible to work under dry atmosphere or in vacuo if necessary. Commarmot, R.; Didenot, R.; Gardais, J. F. French Patent 84/03496, 1986; Chem. Abstr. 1986, 105, 17442. A CEM Discover™ focused microwave reactor (300 W, monomode system) which has in situ magnetic variable speed, may also be used.
30. (a) Frère S., Thiéry V., Besson T. Tetrahedron Lett. 42:2001;2791-2794
31. (b) Soukri M., Guillaumet G., Besson T., Aziane D., Aadil M., Essassi E.M., Akssira M. Tetrahedron Lett. 41:2000;5857-5860.
32. Anastassiadou M., Danoun S., Crane L., Baziard-Mouysset G., Payard M., Caignard D.-H., Rettori M.-C., Renard P. Bioorg. Med. Chem. 9:2001;585-592. and references cited therein.
33. 50 values >5 μM. Other cell lines are currently tested and the results of the biological and pharmacological studies will be reported in due course.
34. English R.F., Rakitin O.A., Rees C.W., Vlasova O.G. J. Chem. Soc., Perkin Trans. 1. 1997;201-205.