Uvaricin
| (+)-Uvaricin | |
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3-(13-(5′-(1-(acetyloxy)undecyl)octahydro(2,2′-bifuran) -5-yl)-13-hydroxytridecyl)-5-methyl-2(5H)-Furanone |
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| Identifiers | |
| CAS number | 82064-83-3  |
| PubChem | 441645 |
| ChemSpider | 390275  |
| KEGG | C08572 |
| ChEMBL | CHEMBL504329 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C39H68O7 |
| Molar mass | 648.95 g mol−1 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Uvaricin is a bis(tetrahydrofuranoid) fatty acid lactone that was first isolated in 1982 from the roots of Uvaria accuminata.[1] Uvaricin was the first in a class of compounds with potent anticancer activity known as acetogenins. Acetogenins, which are found in plants of the family Annonaceae, seem to kill cells by inhibiting NADH dehydrogenase in the mitochondrion.[2] A method to synthesize uvaricin was first published in 1998,[3] and an improved stereoselective synthesis published in 2001.[4]
[edit] References
- ^ Jolad, S. D.; Hoffmann, J. J.; Schram, K. H.; Cole, J. R.; Tempesta, M. S.; Kriek, G. R.; Bates, R. B. (1982). "Uvaricin, a new antitumor agent from Uvaria accuminata (Annonaceae)" ([dead link] – Scholar search). The Journal of Organic Chemistry 47 (16): 3151–3153. doi:10.1021/jo00137a024. http://pubs.acs.org/cgi-bin/abstract.cgi/joceah/1982/47/i16/f-pdf/f_jo00137a024.pdf?sessid=6006l3.
- ^ Zafra-Polo, M. C.; González, M. C.; Estornell, E.; Sahpaz, S.; Cortes, D. (1996). "Acetogenins from annonaceae, inhibitors of mitochondrial complex I". Phytochemistry 42 (2): 253–271. doi:10.1016/0031-9422(95)00836-5. PMID 8688168. http://linkinghub.elsevier.com/retrieve/pii/0031942295008365.
- ^ Yazbak, A.; Sinha, S. C.; Keinan, E. (1998). "Total Synthesis of Uvaricin". J. Org. Chem 63 (17): 5863–5868. doi:10.1021/jo980453a. PMID 11672188. http://www.technion.ac.il/~keinanj/pub/92.pdf.
- ^ Burke, S. D.; Jiang, L. (2001). "Formal Synthesis of Uvaricin via Palladium-Mediated Double Cyclization". Organic Letters 3 (12): 1953–1956. doi:10.1021/ol0160304. PMID 11405753. http://pubs.acs.org/cgi-bin/abstract.cgi/orlef7/2001/3/i12/abs/ol0160304.html.
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