A new family of potential oncostatics: 2-Chloroethylnitrososulfamides (CENS) - I. Synthesis, structure, and pharmacological evaluation (preliminary results)

Bioorganic and Medicinal Chemistry

Volumn 4, Issue 8, 1996, Pages 1227-1235

  Abdaoui, Mohamed ^a   Dewynter, Georges ^a   Aouf, Nourredine ^a,b   Favre, Gilles ^c   Morère, Alain ^a   Montero, Jean Louis ^a  

^a UNIV MONTPELLIER   (France)

^b BADJI MOKHTAR UNIVERSITY   (Algeria)

^c INSTITUT CLAUDIUS REGAUD   (France)

Author keywords

A549; Alkylating agent; Biological screening; Carboxylsulfamide; Chloroethylnitrosoureas; Chlorosulfonyl isocyanate; MCF7; Mitsunobu reaction; Nitrososulfamide; Oncostatics

Indexed keywords

ALKYLATING AGENT; BOFUMUSTINE; CHLOROETHYLNITROSOUREA DERIVATIVE; SULFANILAMIDE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL LINE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030221103     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/0968-0896(96)00118-6     Document Type: Article

References (34)

1. 1. (a) Johnston, T. P.; McCaleb, G. S.; Opliger, P. S.; Laster, Jr W. R.; Montgomery, J. A. J. Med. Chem. 1971, 14, 600, and references therein.
2. (b) Calabresi, P.; Schein, P. S.; Rosenberg, S. A., Eds. Medical Oncology; Macmillan: New York, 1985.
3. (c) Carter, S. K.; Bakowski, M. T.; Hellman, K. Chemotherapy of Cancer 3rd edn; Churchill Livingstone: New York, 1987.
4. (d) Montgomery, J. A.; Mayo, J. G.; Hansch, C. J. J. Med. Chem. 1974, 17, 477.
5. (e) Hansch, C. J.; Leo, A.; Schmidt, C.; Jow, P. Y. C.; Montgomery, J. A. J. Med. Chem. 1980, 23, 848, and references therein.
6. (f) Hansch, C. J.; Leo, A.; Schmidt, C.; Jow, P. Y. C.; Montgomery, J. A. J. Med. Chem. 1980, 23, 1095.
7. (g) Eisenbrand, G. In Relevance of N-Nitroso Compounds to Human Cancer: Exposure and Mechanisms Bartsch, H.; O'Neill, I. K.; Schulte-Herman, R., Eds.; International Agency for Research on Cancer, Lyon, France; 1984, p 685.
8. (h) Sosnovsky, G. Pure Appl. Chem. 1990, 62, 289, and references therein.
9. (i) Dulude, H.; Salvador, R.; Gallant, G. Bioorg. Med. Chem. 1995, 3, 151.
10. 2. White, E. H.; Min Li; Shanzheng Lu J. Org. Chem. 1992, 57, 1252.
11. 3. (a) de Boer, Th. J.; Backer, H. J. Rec. Trav. Chim. Pays-Bas 1954, 73, 229.
12. (b) de Boer Th. J.; Backer, H. J. Org. Synth. Coll. 1963, 4, 250.
13. (c) Hudlicky, M. J. Org. Chem. 1980, 45, 5377.
14. 4. For a review see: Sulfamic Acid and its N-substituted Derivatives. Benson, G. A.; Spillane, W. J. Chem. Rev. 1980, 80, 151.
15. 5. Hamprecht, G.; König, K.-H.; Stubenrauch, G. Angew. Chem. Int. Ed. Engl. 1981, 20, 151.
16. 6. Dewynter, G.-F.; Montera, J.-L. C-R. Acad. Sci. Paris, Série II 1992, 315, 1675.
17. 7. (a) Graf, R. Angew. Chem. 1968, 80, 179.
18. (b) Graf, R. Angew. Chem. Int. Ed. Engl. 1968, 7, 172.
19. (c) Rasmussen, J. K.; Hassner, A. Chem. Rev. 1976, 76, 389.
20. (d) Szabo, W. A.; Aldrichim. Acta 1977, 10, 23.
21. (e) Dhar, D. N.; Murthy, K. S. K. Synthesis 1986, 437.
22. (f) Dewynter, G.-F.; Montera, J.-L.; Agoh, B.; Leydet, A.; Doukhan, G. Phosphorus, Sulf. 1991, 61, 223.
23. 8. (a) Mitsunobu, O. Synthesis 1981, 1.
24. (b) Hughes, D. L. Org. React. 1992, 42, 335.
25. (c) Kim, M.-J.; Hennen, W. J.; Sweers, H. M.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 6481.
26. (d) Wada, M.; Mitsunobu, O. Tetrahedron Lett. 1972, 1279.
27. (e) Koppel, I.; Koppel, J.; Degerbeck, F.; Grehn, L.; Ragnarsson, U. J. Org. Chem. 1991, 56, 7172.
28. (f) Henry, K. R.; Marcin, L. R.; McIntosh, M. C.; Scoli, P. M.; Harris, G. D.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 5709.
29. 9. Montero, J.-L.; Leydet, A.; Dewynter, G.-F.; Messier, A.; Imbach, J.-L. Ann. Univ. Côte d'Ivoire (Ser C) 1983, XIX, 193. Montero, J.-L.; Leydet, A.; Dewynter, G.-F.; Messier A.; Imbach, J.-L. Eur. J. Med. Chem. 1984, 19, 512.
30. 9. Montero, J.-L.; Leydet, A.; Dewynter, G.-F.; Messier, A.; Imbach, J.-L. Ann. Univ. Côte d'Ivoire (Ser C) 1983, XIX, 193. Montero, J.-L.; Leydet, A.; Dewynter, G.-F.; Messier A.; Imbach, J.-L. Eur. J. Med. Chem. 1984, 19, 512.
31. 10. (a) Mathé, G.; Serrou, B.; Hayat, M.; Vassal F.; Misset, J.-L.; Schwarzenberg, L.; Machover, D.; Ribaud, P.; Belpomme, D.; Jasmin, C.; Musset, M.; Montero, J.-L.; Imbach, J.-L. Biomedicine 1977, 27, 294.
32. (b) Montero, J.-L.; Rodriguez, M.; Imbach, J.-L. Eur. J. Med. Chem. 1977, 12, 408.
33. (c) Hayat, M.; Bourut, C.; Montero, J.-L.; Imbach, J.-L.; MacDonald, J. S.; Mathé, G. Cancer Chemother, Pharmacol. 1979, 3, 217.
34. 11. Lestavel-Delattre, S.; Martin-Nizard, F.; Clavey, V.; Testard, P.; Favre, G.; Doualin, G.; Houssaini, H. S.; Bard, J.-M.; Duriez, P.; Delbard, C; Soula, G.; Lesieur, D.; Lesieur, I.; Cazin, J.-C; Cazin, M.; Fruchard, J.-C. Cancer Res. 1992, 52, 3629.