Synthesis of oxychelerythrine using lithiated toluamide-benzonitrile cycloaddition

Chemical and Pharmaceutical Bulletin

Volumn 53, Issue 1, 2005, Pages 118-120

  Le, Thanh Nguyen ^a   Cho, Won Jea ^a  

^a Chonnam National University   (South Korea)

Author keywords

Benzo c phenanthridine; Cycloaddition; Oxychelerythrine

Indexed keywords

ALKALOID; BENZO[C]PHENANTHRIDINE DERIVATIVE; BENZONITRILE; CHELERYTHRINE; OXYCHELERYTHRINE; UNCLASSIFIED DRUG; BENZOPHENANTHRIDINE DERIVATIVE; NITRILE; PHENANTHRIDINE DERIVATIVE; TOLUENE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

ALKALOIDS; BENZOPHENANTHRIDINES; NITRILES; PHENANTHRIDINES; TOLUENE;

EID: 18744383369     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.53.118     Document Type: Article

References (17)

1. Hoffmann T. K., Leenen K., Hafner D., Balz V., Gerharz C. D., Grund A., Ballo H., Hauser U., Bier H., Anti-Cancer Drugs, 13, 93-100 (2002).
2. Chmura S. J., Dolan M. E., Cha A., Mauceri H. J., Kufe D. W., Weichselbaum R. P., Clinical Cancer Research, 6, 737-742 (2000).
3. Yu R., Mandlekar S., Tan T.-H., Kong A.-N. T., J. Biol. Chem., 275, 9612-9619 (2000).
4. Yamamoto S., Seta K., Morisco C., Vatner S. F., Satoshima J., J. Mol. Cell Cardiol., 33, 1829-1848 (2001).
5. Lou H., Ookhtens M., Stolz A., Kaplowitz N., Am. J. Physiol. Gastrointest. Liver Psysiol., 285, G1335-G1344 (2003).
6. Chan S.-L., Lee M. C., Tan K. O., Yang L.-K., Lee A. S. Y., Flotow H., Fu N. Y., Butler M. S., Soejarto D. D., Buss A. D., Yu V. C., J. Biol. Chem., 278, 20453-20456 (2003).
7. Nakanishi T., Suzuki M., Org. Lett., 1, 985-988 (1999).
8. Geen G. R., Mann I. S., Mullane M. V., Mckillop A., Tetrahedron, 54, 9875-9894 (1998).
9. Harayama T., Akamatsu H., Okamura K., Miyagoe T., Akiyama T., Abe H., Takeuchi Y., J. Chem. Soc., Perkin Trans. I, 2001, 523-528.
10. Treus M., Estevez J. C., Castedo L., Estevez R. J., Tetrahedron Lett., 43, 5323-5325 (2002).
11. Simanek V., "The Aklaloids, Chemistry and Pharmacology," Vol. 26, ed. by Brossi A., Academic Press, Orlando, 1985, pp. 185-240, and references cited therein.
12. Le T. N., Gang S. G., Cho W.-J., J. Org. Chem., 69, 2768-2772 (2004).
13. Le T. N., Gang S. G., Cho W.-J., Tetrahedron Lett., 45, 2763-2766 (2004).
14. Sahakitpichan P., Ruchirawat S., Tetrahedron, 60, 4169-4172 (2004).
15. Mackay S. P., Meth-Cohn O., Waich R. D., "Advances in Heterocyclic Chemistry," Vol. 67, ed. by Katritzky A. R., Academic Press, Orlando, 1997, pp. 345-389, and references cited therein.
16. Kessar S. V., Singh P., Vohra R., Kaur N. P., Venugopal D., J. Org. Chem., 57, 6716-6720 (1992).
17. Hanaoka M., Motonishi T., Mukai C., J. Chem. Soc., Perkin Trans. I, 1986, 2253-2256.