The Suzuki-Miyaura reaction in the chemical transformations of vindoline

• Authors: Joanna Ruszkowska , Robert Chrobak , Paweł Żero , Jan K Maurin , Joanna Szawkało , Zbigniew Czarnocki
• Languages of publication: EN

Abstracts

EN

Vindoline and its analogues are important constituents of the Madagascan periwinkle Catharanthus roseus, and some of them are valuable chemotherapy drugs used in treatment for some types of cancer, including leukaemia, lymphoma, breast and lung cancer. The search for semi-synthetic congeners of natural substances is still an important task for organic chemistry. In this communication we report the synthesis of five new vindoline derivatives, 15-(2-methoxyphenyl)vindoline 11, 15-(3-methoxyphenyl)vindoline 12, 15-(2-nitrophenyl)vindoline 13, 15-(3-cyanophenyl)vindoline 15, and 15-(4-cyanophenyl)vindoline 16 using the Suzuki-Miyaura reaction as the key step. X-Ray analysis of compound 16 is also reported.

Keywords

EN

alkaloids; chemotherapy; bioorganic chemistry; natural products

• Publisher: Polish Biochemical Society
• Journal: Acta Biochimica Polonica
• Year: 2007
• Volume: 54
• Issue: 4
• Pages: 857-861

Dates

published

2007

received

2007-07-17

revised

2007-09-23

accepted

2007-09-24

(unknown)

2007-12-08

Contributors

author

Joanna Ruszkowska

• Faculty of Chemistry, Warsaw University, Warszawa, Poland

author

Robert Chrobak

• Faculty of Chemistry, Warsaw University, Warszawa, Poland

author

Paweł Żero

• Faculty of Chemistry, Warsaw University, Warszawa, Poland

author

Jan K Maurin

• National Medicines Institute, Warszawa, Poland

author

Joanna Szawkało

• Faculty of Chemistry, Warsaw University, Warszawa, Poland

author

Zbigniew Czarnocki

• Faculty of Chemistry, Warsaw University, Warszawa, Poland

References

• Berrier C, Jacquesy JC, Jouannetaud MP, Lafitte C, Vidal Y, Zunino F, Fahy J, Duflos A (1998) Tetrahedron 54: 13761-13770.
• Błachut D, Wojtasiewicz K, Czarnocki Z (2006) Synthesis 17: 2855-2864.
• Brossi A, ed (1990) Antitumor Bisindole Alkaloids from Catharanthus roseus (L.), The Alkaloids, vol 37, Academic Press.
• Choi Y, Ishikawa H, Velcicky J, Elliott GI, Miller MM, Boger DL (2005) Org Lett 7: 4539-4542.
• Danieli B, Lesma G, Martinelli M, Passarella D, Silvani A (1998) J Org Chem 63: 8586-8588.
• Fekete M, Kolonits P, Novak L (2005) Heterocycles 65: 165-171.
• Hirata K, Duangteraprecha S, Morihara E, Honda M, Akagi T, Nakae M, Katayama H, Miyamoto K (1997) Biotechnol Lett 19: 53-57.
• Ishikawa H, Elliott GI, Velcicky J, Choi Y, Boger DL (2006) J Am Chem Soc 128: 10596-10612.
• Kotha S, Lahiri K, Kashinath D (2002) Tetrahedron 58: 9633-9695.
• Kutney JP, Hibino T, Jahngen E, Okutani T, Ratcliffe AH, Treasurywala AM, Wunderly S (1976) Helv Chim Acta 59: 2858-2882.
• Langlois N, Gueritte F, Langlois Y, Potier P (1976) J Am Chem Soc 98: 7017-7024.
• Leveque D, Wihlm J, Jehl F (1996) Bull Cancer 83: 176-186.
• Littke AF, Fu GC (2002) Angew Chem Int Ed Engl 41: 4176-4211.
• Ruszkowska J, Macierewicz B, Wróbel JT (1994) P 164 944; C 07D 519/04.
• Ruszkowska J, Chrobak R, Wróbel JT, Czarnocki Z (2003) Adv Exp Med Biol 527: 643-646.
• Ruszkowska J, Chrobak R, Maurin JK, Czarnocki Z (2004) Acta Crystallogr C 60: 377-380.
• Sheldrick GM (1997) SHELXL97 Program for the solutions of crystal structures. University of Goettingen, Germany.
• Schröter S, Stock C, Bach T (2005) Tetrahedron 61: 2245-2267.
• Sundberg RJ, Hong J, Smith SQ, Sabat M, Tabakovic I (1998) Tetrahedron 54: 6259-6292.
• Suzuki A (1999) J Organomet Chem 576: 147-168.
• Tabakovic I, Gunic E, Juranic I (1997) J Org Chem 62: 947-953.
• Taylor WI, Farnsworth NR, eds, (1975) The Catharanthus Alkaloids, Marcel Dekker Inc., New York.
• Thimmaiah M, Fang S (2007) Tetrahedron 63: 6879-6886.
• Van der Heijden R, Jacobs DI, Snoeijer W, Hallared D, Verpoorte R (2004) Curr Med Chem 11: 607-628.