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F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
The Madagascan periwinkle Catharanthus roseus L. is the source for a number of important natural products,[1] including catharanthine and vindoline [2] and the vinca alkaloids it produces from them: leurosine and the chemotherapy agents vinblastine [3] and vincristine ,[4] all of which can be obtained from the plant.[5] [6] [7] [8] The newer semi-synthetic chemotherapeutic agent vinorelbine is used in the treatment of non-small-cell lung cancer [7] [9] and is not known to occur naturally. However, it can be prepared either from vindoline and catharanthine[7] [10] or from leurosine,[11] in both cases by synthesis of anhydrovinblastine, which "can be considered as the key intermediate for the synthesis of vinorelbine."[7] The leurosine pathway uses the Nugent–RajanBabu reagent in a highly chemoselective de-oxygenation of leurosine.[12] [11] Anhydrovinblastine is then reacted sequentially with N -bromosuccinimide and trifluoroacetic acid followed by silver tetrafluoroborate to yield vinorelbine.[10]
Applications
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Vinca alkaloids are used in chemotherapy for cancer. They are a class of cell cycle –specific cytotoxic drugs that work by inhibiting the ability of cancer cells to divide: Acting upon tubulin, they prevent it from forming into microtubules , a necessary component for cellular division .[13] The vinca alkaloids thus prevent microtubule polymerization , as opposed to the mechanism of action of taxanes .
Vinca alkaloids are now produced synthetically and used as drugs in cancer therapy and as immunosuppressive drugs. These compounds include vinblastine, vincristine, vindesine , and vinorelbine. Additional researched vinca alkaloids include vincaminol , vineridine , and vinburnine .
Vinpocetine is a semi-synthetic derivative of vincamine (sometimes described as "a synthetic ethyl ester of apovincamine").[14]
Minor vinca alkaloids include minovincine, methoxyminovincine, minovincinine, vincadifformine, desoxyvincaminol, and vincamajine.[15] [16] [17]
References
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^ Sears, Justin E.; Boger, Dale L. (2015). "Total Synthesis of Vinblastine, Related Natural Products, and Key Analogues and Development of Inspired Methodology Suitable for the Systematic Study of Their Structure-Function Properties" . Accounts of Chemical Research . 48 (3 ): 653–662. doi :10.1021/ar500400w . PMC 4363169 . PMID 25586069 .
^ Kuboyama, Takeshi; Yokoshima, Satoshi; Tokuyama, Hidetoshi; Fukuyama, Tohru (2004). "Stereocontrolled total synthesis of (+)-vincristine" . Proceedings of the National Academy of Sciences of the United States of America . 101 (33 ): 11966–11970. Bibcode :2004PNAS..10111966K . doi :10.1073/pnas.0401323101 . PMC 514417 . PMID 15141084 .
^ Gansäuer, Andreas; Justicia, José; Fan, Chun-An; Worgull, Dennis; Piestert, Frederik (2007). "Reductive C—C bond formation after epoxide opening via electron transfer" . In Krische, Michael J. (ed.). Metal Catalyzed Reductive C—C Bond Formation: A Departure from Preformed Organometallic Reagents . Topics in Current Chemistry. Vol. 279. Springer Science & Business Media . pp. 25–52. doi :10.1007/128_2007_130 . ISBN 9783540728795 .
^ Cooper, Raymond; Deakin, Jeffrey John (2016). "Africa's gift to the world" . Botanical Miracles: Chemistry of Plants That Changed the World . CRC Press . pp. 46–51. ISBN 9781498704304 .
^ a b c d Keglevich, Péter; Hazai, Laszlo; Kalaus, György; Szántay, Csaba (2012). "Modifications on the basic skeletons of vinblastine and vincristine" . Molecules . 17 (5 ): 5893–5914. doi :10.3390/molecules17055893 . PMC 6268133 . PMID 22609781 .
^ Raviña, Enrique (2011). "Vinca alkaloids" . The evolution of drug discovery: From traditional medicines to modern drugs . John Wiley & Sons . pp. 157–159. ISBN 9783527326693 .
^ Faller, Bryan A.; Pandi, Trailokya N. (2011). "Safety and efficacy of vinorelbine in the treatment of non-small cell lung cancer" . Clinical Medicine Insights: Oncology . 5 : 131–144. doi :10.4137/CMO.S5074 . PMC 3117629 . PMID 21695100 .
^ a b Ngo, Quoc Anh; Roussi, Fanny; Cormier, Anthony; Thoret, Sylviane; Knossow, Marcel; Guénard, Daniel; Guéritte, Françoise (2009). "Synthesis and biological evaluation of Vinca alkaloids and phomopsin hybrids". Journal of Medicinal Chemistry . 52 (1 ): 134–142. doi :10.1021/jm801064y . PMID 19072542 .
^ a b Hardouin, Christophe; Doris, Eric; Rousseau, Bernard; Mioskowski, Charles (2002). "Concise synthesis of anhydrovinblastine from leurosine". Organic Letters . 4 (7 ): 1151–1153. doi :10.1021/ol025560c . PMID 11922805 .
^ Morcillo, Sara P.; Miguel, Delia; Campaña, Araceli G.; Cienfuegos, Luis Álvarez de; Justicia, José; Cuerva, Juan M. (2014). "Recent applications of Cp2 TiCl in natural product synthesis" . Organic Chemistry Frontiers . 1 (1 ): 15–33. doi :10.1039/c3qo00024a . hdl :10481/47295 .
^ Takimoto, C. H.; Calvo, E. (2008). "Chapter 3: Principles of Oncologic Pharmacotherapy" . In Pazdur, R.; Wagman, L. D.; Camphausen, K. A.; Hoskins, W. J. (eds.). Cancer Management: A Multidisciplinary Approach (11th ed.). ISBN 978-1-891483-62-2 . Archived from the original on 2009-05-15. Retrieved 2011-05-26 .
^ Lörincz C, Szász K, Kisfaludy L (1976). "The synthesis of ethyl apovincaminate". Arzneimittel-Forschung . 26 (10a): 1907. PMID 1037211 .
^ Plat, M; Fellion, E; Le Men, J; Janot, M (1962). "4 new alkaloids of Vinca minor L.: minovincine, methoxyminovincine, minovincinine and (-) vincadifformine, alkaloids of periwinkles". Ann. Pharm. Fr. (in French). 20 : 899–906. PMID 13943964 .
^ Smeyers, Yves G.; Smeyers, Nadine J.; Randez, Juan J.; Hernandez-Laguna, A.; Galvez-Ruano, E. (1991). "A structural and pharmacological study of alkaloids of Vinca Minor ". Molecular Engineering . 1 (2 ): 153–160. doi :10.1007/BF00420051 . S2CID 93210480 .
^ Janot, M. M.; Le Men, J; Fan, C (1958). "The alkaloids of the periwinkles (Vinca ): Relation between, vincamedine and vincamajine". Comptes Rendus Hebdomadaires des Séances de l'Académie des Sciences . 247 (25 ): 2375–7. PMID 13619121 .
External links
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R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Vinca_alkaloid&oldid=1170652860 "
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