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Ellipticine

CAT#: H406537

CAS#: 519-23-3

Description: Ellipticine is a DNA intercalating agent and a DNA topoisomerase II inhibitor. Ellipticine is also a natural product, isolated in 1959 from the Australian evergreen tree of the Apocynaceae family. Ellipticine was found to be an extremely promising anticancer drug. The planar polycyclic structure was found to interact with DNA through intercalation, exhibiting a high DNA binding affinity (10(6) M(-1)). The presence of protonatable ring nitrogens distinguished ellipticine from other simple intercalators. Both monocationic and uncharged species were found to be present under physiological conditions. The positive charge stabilized the binding of ellipticine to nucleic acids, while the more lipophilic uncharged compound was shown to readily penetrate membrane barriers. The structural nature of these compounds offers a plausible basis for the implication of multiple modes of action, including DNA binding, interactions with membrane barriers, oxidative bioactivation and modification of enzyme function; most notably that of topoisomerase II and telomerase. ( Curr Med Chem Anticancer Agents. 2004 Mar;4(2):149-72 ).

Synthetic Routes

Ellipticine - Synthetic Route 1

Synthetic reference

Dilek, Omer; Patir, Suleyman; Tilki, Tahir; Erturk, Erkan. Total Synthesis of Olivacine and Ellipticine via a Lactone Ring-Opening and Aromatization Cascade. Journal of Organic Chemistry. Volume 84. Issue 12. Pages 7901-7916. Journal; Online Computer File. (2019).

Ellipticine - Synthetic Route 2

Synthetic reference

Liu, Ching-Yuan; Knochel, Paul. Preparation of Polyfunctional Aryl Azides from Aryl Triazenes. A New Synthesis of Ellipticine, 9-Methoxyellipticine, Isoellipticine, and 7-Carbethoxyisoellipticine. Journal of Organic Chemistry. Volume 72. Issue 19. Pages 7106-7115. Journal. (2007).

Ellipticine - Synthetic Route 3

Synthetic reference

Pedersen, Jan M.; Bowman, W. Russell; Elsegood, Mark R. J.; Fletcher, Anthony J.; Lovell, Peter J. Synthesis of Ellipticine: A Radical Cascade Protocol to Aryl- and Heteroaryl-Annulated[b]carbazoles. Journal of Organic Chemistry. Volume 70. Issue 25. Pages 10615-10618. Journal. (2005).

Ellipticine - Synthetic Route 4

Synthetic reference

Bennasar, M.-Lluiesa; Roca, Tomas; Ferrando, Francesc. Regioselective Intramolecular Reactions of 2-Indolylacyl Radicals with Pyridines: A Direct Synthetic Entry to Ellipticine Quinones. Journal of Organic Chemistry. Volume 70. Issue 22. Pages 9077-9080. Journal. (2005).

Ellipticine - Synthetic Route 5

Synthetic reference

Gribble, Gordon W.; Saulnier, Mark G.; Obaza-Nutaitis, Judy A.; Ketcha, Daniel M. A versatile and efficient construction of the 6H-pyrido[4,3-b]carbazole ring system. Syntheses of the antitumor alkaloids ellipticine, 9-methoxyellipticine, and olivacine, and their analogs. Journal of Organic Chemistry. Volume 57. Issue 22. Pages 5891-9. Journal. (1992).

Ellipticine - Synthetic Route 6

Synthetic reference

Baeckvall, Jan E.; Plobeck, Niklas A. New synthesis of the 6H-pyrido[4,3-b]carbazoles ellipticine and olivacine via cycloaddition of 2-phenylsulfonyl 1,3-dienes to indoles. Journal of Organic Chemistry. Volume 55. Issue 15. Pages 4528-31. Journal. (1990).

Ellipticine - Synthetic Route 7

Synthetic reference

Konakahara, Takeo; Kiran, Y. B.; Okuno, Yuri; Ikeda, Reiko; Sakai, Norio. An expedient synthesis of ellipticine via Suzuki-Miyaura coupling. Tetrahedron Letters. Volume 51. Issue 17. Pages 2335-2338. Journal. (2010).

Ellipticine - Synthetic Route 8

Synthetic reference

Miki, Yasuyoshi; Aoki, Yoshiyuki; Tsuzaki, Yasuhiko; Umemoto, Misako; Hibino, Hajime. Synthesis of 3-methoxyellipticine and ellipticine by Friedel-Crafts reaction of indole-2,3-dicarboxylic anhydride and selective demethylation. Heterocycles. Volume 65. Issue 11. Pages 2693-2703. Journal. (2005).

Ellipticine - Synthetic Route 9

Synthetic reference

Deane, Fiona M.; Miller, Charlotte M.; Maguire, Anita R.; McCarthy, Florence O. Modifications to the Vilsmeier-Haack formylation of 1,4-dimethylcarbazole and its application to the synthesis of ellipticines. Journal of Heterocyclic Chemistry. Volume 48. Issue 4. Pages 814-823. Journal; Online Computer File. (2011).

Ellipticine - Synthetic Route 10

Synthetic reference

Rasheed, Sk.; Rao, Desaboini Nageswar; Das, Parthasarathi. Nickel-Catalyzed C(Aryl)-O Bond Activation/Cross-Coupling Reaction of Carbazoles with Methyl Grignard: Synthesis of Ellipticine. Asian Journal of Organic Chemistry. Volume 5. Issue 12. Pages 1499-1507. Journal; Online Computer File. (2016).