Synthesis and radical scavenging activity of 3,3-dialkyl-3,4-dihydro-isoquinoline 2-oxides

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 10, 1996, Pages 1105-1110

  Bernotas, Ronald C ^a   Thomas, Craig E ^a   Carr, Albert A ^a   Nieduzak, Thaddeus R ^a   Adams, Ginette ^a   Ohlweiler, David F ^a   Hay, David A ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

LETHRINIDAE;

2,2' AZOBIS(2 AMIDINOPROPANE); 3,4 DIHYDROISOQUINOLINE 2 OXIDE; FORMAMIDE; ISOQUINOLINE DERIVATIVE; LIPOSOME; N TERT BUTYL ALPHA PHENYLNITRONE; POLYPHOSPHATE; SCAVENGER; THIOBARBITURIC ACID REACTIVE SUBSTANCE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CYCLIZATION; DRUG OXIDATION; DRUG POTENCY; DRUG SYNTHESIS; LIPID PEROXIDATION; LIPOPHILICITY; NONHUMAN; SEPTIC SHOCK; STROKE;

EID: 0029938807     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00181-3     Document Type: Article

References (25)

1. Biasi, F.; Chiarpotto, E.; Lanfranco, G.; Capra, A.; Zummo, U.; Chiappino, I.; Scavazza, A.; Albano, E.; Poli, G. Free Rad. Biol. Med. 1994,17, 225.
2. Kontos, H. A. Chem.-Biol. Interactions 1989, 72, 229.
3. Hamburger, S. A.; McCay, P. B. Circ. Shock 1989, 29, 329.
4. Oliver, C. N.; Starke-Reed, P. E.; Stadtman, E. R.; Liu, G. J.; Carney, J. M.; Floyd, R. A. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 5144.
5. More recent studies indicate PBN is more planar than 2a. Thomas, C. E.; Ohlweiler, D. F.; Carr, A. A.; Nieduzak, T. R.; Hay, D. A.; Adams, G.; Vaz, R.; Bernotas, R. C. J. Biol. Chem. 1996, 271, 3097.
6. Thomas, C. E.; Carney, J. M.; Bernotas, R. C.; Hay, D. A.; Carr, A. A. Annals NY Acad. Sci. 1994, 234, 243.
7. French, J. F.; Thomas, C. E.; Downs, T. R.; Ohlweiler, D. F.; Carr, A. A.; Dage, R. C. Circ. Shock 1994, 43, 130.
8. Seeger, E.; Engel, W.; Teufel, H.; Machleidt, H. Chem. Ber. 1970, 103, 1674. Nordlander, J. E.; Payne, M. J.; Njoroge, F. G.; Balk, M. A.; Laikos, G. D.; Vishwanath, V. M. J. Org. Chem. 1984, 49, 4107.
9. Seeger, E.; Engel, W.; Teufel, H.; Machleidt, H. Chem. Ber. 1970, 103, 1674. Nordlander, J. E.; Payne, M. J.; Njoroge, F. G.; Balk, M. A.; Laikos, G. D.; Vishwanath, V. M. J. Org. Chem. 1984, 49, 4107.
10. Ritter, J. J.; Kalish, J. Organic Synthesis, 1964, 44, 44.
11. Review: Whaley, W. M.; Govindachari, T. R. In Organic Reactions; Adams, R., Ed.; Wiley and Sons: New York, 1951; Vol. 6, pp 74-150.
12. Murahashi, S.; Shiota, T.; Imada, Y. Org. Synth. 1991, 70, 265.
13. 13C NMR, CIMS or EIMS, and IR).
14. Baker, G. B.; Coutts, R. T.; Benderly, A.; Cristofoli, W. A.; Dewhurst, W. G. Can. J. Pharm. Sci. 1981, 15, 71.
15. Larsen, R. D.; Reamer, R. A.; Corley, E. G.; Davis, P.; Grabowski, E. J. J.; Reider, P. J.; Shinkai, I. J. Org. Chem. 1991, 56, 6034.
16. Satisfactory elemental analyses were difficult to obtain so the crude imines were generally used without further purification.
17. See Krimen, L. I.; Cota, D. J. In Organic Reactions; Dauben, W. G., Ed.; Wiley and Sons: New York, 1969; Vol. 17, pp 213-325.
18. This reaction could be run with or without addition of the copper catalyst. For examples, see Najera, C.; Sansano, J. M. Tetrahedron Lett. 1993, 34, 3781. Rahman, M. T.; Nahar, S. K. J. Organomet. Chem. 1987, 329, 133. Residual biaryl contaminants were readily removed after the Ritter reaction.
19. This reaction could be run with or without addition of the copper catalyst. For examples, see Najera, C.; Sansano, J. M. Tetrahedron Lett. 1993, 34, 3781. Rahman, M. T.; Nahar, S. K. J. Organomet. Chem. 1987, 329, 133. Residual biaryl contaminants were readily removed after the Ritter reaction.
20. Aryl substituted alcohols of type 3 were also used if readily available.
21. The alcohols were synthesized by addition of a benzyl Grignard reagent to cyclopentanone or cyclohexanone. Pallos, L.; Zolyomi, G.; Budai, Z; Komlos, E.; Petocz, L. E. Hungarian patent 151 865, 1965; Chem. Abstr. 1965, 62, 16125b.
22. The alcohols were synthesized by addition of a benzyl Grignard reagent to cyclopentanone or cyclohexanone. Pallos, L.; Zolyomi, G.; Budai, Z; Komlos, E.; Petocz, L. E. Hungarian patent 151 865, 1965; Chem. Abstr. 1965, 62, 16125b.
23. Thomas, C. E.; McLean, L. R.; Parker, R. A.; Ohlweiler, D. F. Lipids 1992, 27, 543.
24. Leo, A. J. Chem. Rev. 1993, 93, 1281.
25. Available from Daylight Chemical Information Systems, Inc., Irvine, CA, USA.