A simple, general and efficient method for O and N-retinoylation. Application to the synthesis of 2-retinoyl-lecithin

Synthetic Communications

Volumn 28, Issue 16, 1998, Pages 2945-2958

  Sangmam, Charles ^a   Winum, Jean Yves ^a   Lucas, Marc ^a   Montero, Jean Louis ^a   Chavis, Claude ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1 STEAROYL 2 RETINOYLGLYCERO 3 PHOSPHOCHOLINE; LYSOPHOSPHATIDYLCHOLINE; RETINOIC ACID; RETINOIC ACID RECEPTOR; RETINOL DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DERIVATIZATION; ESTERIFICATION; GEL CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0031880119     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808004874     Document Type: Article

References (31)

1. Mehta, K.; Sadeghi, T.; McQueen, T.; Lopez-Berestein, G. Leukemia Res. 1994, 18, 587.
2. a) Malkin, D.; Li, F.; Strong, L. C.; Fraumeni, J. F.; Nelson, C. E.; Kim, D. H.; Kassel, J.; Gryka, G.; Bischoff, F. Z.; Tainsky, M. A.; Friend, S. H. Science, 1990, 250, 1233.
3. b) Doerksen, L. F.; Bhattacharya, A.; Kannan, P.; Tainsky, M. A. Nucleic. Acids Res., 1996, 14, 2849.
4. Semba, R. D. Clin. Infect. Dis., 1994, 19, 489.
5. Butturini, U. Acta Vitaminol. Enzymol. (Italy), 1982, 4, 15.
6. Israel, L; Aguilera, J. Pathol. Biol. (France), 1980, 28, 253.
7. Shealy, Y. F.; Frye, J. L; Schiff, L. J. J. Med. Chem., 1988, 31, 190.
8. Kochhar, D. M. Cong. Anom., 1994, 35, 55.
9. Biesalsky, H. S.; Doepner, G.; Kunz, H.; Paust, J.; John, M. Liebigs Ann. Chem., 1995, 4, 717.
10. Agnaniet, H. Synthèse et Activité Biologique d'Antiviraux dérivant de la Thymidine, Thèse de Doctorat de l'Université de Montpellier II, 1992.
11. Huidman, H. O.; Smit, A.; Meltzer, J. Recl. Trav. Chim. Pays-Bas, 1958, 77, 97.
12. Shealy, Y. F.; Frye, J. L.; O'Dell, C. A.; Thorpe, M. C.; Kirk, M. C.; Coburn, W. C.; Sporn, M. B. J. Pharm. Sci., 1984, 73, 745.
13. Zakharova, N. I.; Yu Gorina, N.; Samokhvalov, G. I.; Fillipova, T. M. Zh. Org. Khim., 1991, 27, 1183.
14. König, H.; Peh, J.; Scholz, H.; Paust, J. German Pat. 2,300,107, July 11, 1974.
15. Aggarwal, S. K.; Gogu, S. R.; Rangan, S. R. S.; Agrawal, K. C. J. Med. Chem., 1990, 53, 1505.
16. Barua, A. B.; Olson, J. A. J. Lipid Res., 1985, 26, 1277.
17. Barua, A. B.; Huselton, C. A.; Olson, J. A. Synth. Commun. 1996, 26, 1355.
18. Camplo, M.; Faury, P.; Charvet, A. S.; Graciet, J. C.; Chermann, J. C.; Kraus, J. L. Eur. J. Med. Chem., 1994, 29, 357.
19. Staab, H.; Mannchreck, A. Chem. Ber., 1962, 95, 1284.
20. Staab, H.; Bräuling, H. Liebigs Ann. Chem., 1962, 654, 119.
21. Staab, H. Angew. Chem., 1962, 74, 407.
22. Carlon, F. E.; Draper, R. W. Synth. Commun., 1984, 14, 725.
23. Singh, A. K. Synth. Commun., 1982, 12, 7447.
24. Mc Cully, K. S. United States Pat. 4,618,685, Oct. 21, 1986.
25. Regen, S. L.; Singh, A.; Oehme, G.; Singh, M., J. Am. Chem. Soc., 1982, 4, 781.
26. Cubero, R. E.; Van den Berg, D., Biochim. Biophys. Acta, 1969, 187, 520.
27. Neises, B.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 522.
28. a) Moon, R. C.; Thompson, H. J.; Becci, P. J.; Grubbs, C. J.; Gander, R. J.; Newton, D. L.; Smith, J. M.; Phillips, S. L.; Henderson, W. R.; Mullen, L. T.; Brown, C.C.; Sporn, M. B. Cancer Res., 1979, 39, 1339.
29. b) Formelli, F.; Barua, A. B.; Olson, J.A. FASEB J., 1996, 10, 1014.
30. Villeneuve, G. B.; Chan, T. H., Tetrahedron Lett., 1997, 38, 6489.
31. We are deeply indebted to Professor T.H. CHAN and Dr. G. VILLENEUVE for personal communication on experimental procedure related to the purification of this unstable compound.