Camptothecin (CPT) is a cytotoxic quinoline alkaloid,
which inhibits the DNA enzyme topoisomerase I (topo I). It was
discovered in 1966 by M. E. Wall and M. C. Wani in systematic
screening of natural products for anticancer drugs. It was isolated
from the bark and stem of Camptotheca acuminata (Camptotheca,
Happy tree), a tree native in China. CPT showed remarkable
anticancer activity in preliminary clinical trials but also low
solubility and (high) adverse drug reaction. Because of these
disadvantages synthetic and medicinal chemists have developed
numerous syntheses of Camptothecine [1][2][3] and various
derivatives to increase the benefits of the chemical, with good results.
In our method CPT analogues has be six steps starting from available
material DL Malic acid.
[1] Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. Synth. Commun. 1995, 25,
1947. (b) Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem.
1995, 60, 7149. (c) Lee, J. Y.; Lee, Y. S.; Chung, B. Y.; Park, H.
Tetrahedron 1997, 53, 2449. (d) Lee, Y. S.; Kang, S. S.; Choi, J. H.;
Park, H. Tetrahedron 1997, 53, 3045.
[2] Louwrier, S.; Ostendorf, M.; Boom, A.; Hiemstra, H.; Speckamp, W. N.
Tetrahedron 1996, 52, 2603.
[3] Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1991, 56, 4868 et les
références citées.
[4] Chihab-Eddine, A.; Daïch, A.; Jilale, A.; Decroix, B. Tetrahedron Lett.
2001, 42, 573
[5] Marson, C. M.; Pink, J. H.; Hall, D.; Hursthouse, M. B.; Malik, A.;
Smith, C. J. Org. Chem. 2003, 68, 792
[6] Lee, L. S.; Yan, J-.L.; Wang, K. C. Tetrahedron: Asymmetry 1997, 8,
3051.
[7] (a) Cheng, C.-C.; Yan, S.-J. In Organic Reactions; Dauben, W. G., Ed.;
John Wiley & Sons: New York, 1982; Vol. 28, Chapitre 2. (b)
Friedländer, P. Berichte 1882, 15, 2572. (c) Jones, G. In Comprehensive
Heterocyclic Chemistry II; Ramsden, C. A., Ed.; Pergamon Press:
Tarrytown, 1996; Vol. 5., Chapitre 5. (d) Lowe, P. A. In Comprehensive
Heterocyclic Chemistry; Boulton, A. J., McKillop, A., Eds.; Pergamon
Press: New York, 1984; Vol. 2, Chapitre 2.11
[8] (a) Yadav, J. S.; Reddy, B. V. S.; Premalatha, K. Synlett 2004, 963. (b)
Wu, J.; Zhang, L.; Diao, T.-N. Synlett 2005, 2648. (c) De, S. K.; Gibbs,
R. A. Tetrahedron Lett. 2005, 46, 1647. (d) Wang, G-.W.; Jia, C-.S.;
Dong, Y-.W. Tetrahedron Lett. 2006, 47, 1059
[9] Borsche, W.; Ried, W. Justus Liebigs Ann. Chem. 1943, 554, 269
[10] McNaughton, R. B.; Miller, L. Org. Lett. 2003, 5, 4257.
[1] Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. Synth. Commun. 1995, 25,
1947. (b) Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem.
1995, 60, 7149. (c) Lee, J. Y.; Lee, Y. S.; Chung, B. Y.; Park, H.
Tetrahedron 1997, 53, 2449. (d) Lee, Y. S.; Kang, S. S.; Choi, J. H.;
Park, H. Tetrahedron 1997, 53, 3045.
[2] Louwrier, S.; Ostendorf, M.; Boom, A.; Hiemstra, H.; Speckamp, W. N.
Tetrahedron 1996, 52, 2603.
[3] Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1991, 56, 4868 et les
références citées.
[4] Chihab-Eddine, A.; Daïch, A.; Jilale, A.; Decroix, B. Tetrahedron Lett.
2001, 42, 573
[5] Marson, C. M.; Pink, J. H.; Hall, D.; Hursthouse, M. B.; Malik, A.;
Smith, C. J. Org. Chem. 2003, 68, 792
[6] Lee, L. S.; Yan, J-.L.; Wang, K. C. Tetrahedron: Asymmetry 1997, 8,
3051.
[7] (a) Cheng, C.-C.; Yan, S.-J. In Organic Reactions; Dauben, W. G., Ed.;
John Wiley & Sons: New York, 1982; Vol. 28, Chapitre 2. (b)
Friedländer, P. Berichte 1882, 15, 2572. (c) Jones, G. In Comprehensive
Heterocyclic Chemistry II; Ramsden, C. A., Ed.; Pergamon Press:
Tarrytown, 1996; Vol. 5., Chapitre 5. (d) Lowe, P. A. In Comprehensive
Heterocyclic Chemistry; Boulton, A. J., McKillop, A., Eds.; Pergamon
Press: New York, 1984; Vol. 2, Chapitre 2.11
[8] (a) Yadav, J. S.; Reddy, B. V. S.; Premalatha, K. Synlett 2004, 963. (b)
Wu, J.; Zhang, L.; Diao, T.-N. Synlett 2005, 2648. (c) De, S. K.; Gibbs,
R. A. Tetrahedron Lett. 2005, 46, 1647. (d) Wang, G-.W.; Jia, C-.S.;
Dong, Y-.W. Tetrahedron Lett. 2006, 47, 1059
[9] Borsche, W.; Ried, W. Justus Liebigs Ann. Chem. 1943, 554, 269
[10] McNaughton, R. B.; Miller, L. Org. Lett. 2003, 5, 4257.
@article{"International Journal of Chemical, Materials and Biomolecular Sciences:64218", author = "Abdulkareem Hamid and Adam Daïch", title = "Synthesis of Analogue to Camptothecine", abstract = "Camptothecin (CPT) is a cytotoxic quinoline alkaloid,
which inhibits the DNA enzyme topoisomerase I (topo I). It was
discovered in 1966 by M. E. Wall and M. C. Wani in systematic
screening of natural products for anticancer drugs. It was isolated
from the bark and stem of Camptotheca acuminata (Camptotheca,
Happy tree), a tree native in China. CPT showed remarkable
anticancer activity in preliminary clinical trials but also low
solubility and (high) adverse drug reaction. Because of these
disadvantages synthetic and medicinal chemists have developed
numerous syntheses of Camptothecine [1][2][3] and various
derivatives to increase the benefits of the chemical, with good results.
In our method CPT analogues has be six steps starting from available
material DL Malic acid.", keywords = "Camptothecine, synthesis, analogue.", volume = "5", number = "1", pages = "90-4", }