Uvaricin

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(+)-Uvaricin

IUPAC name 3-(13-(5′-(1-(acetyloxy)undecyl)octahydro(2,2′-bifuran) -5-yl)-13-hydroxytridecyl)-5-methyl-2(5H)-Furanone
Identifiers
CAS number	82064-83-3^N
PubChem	441645
ChemSpider	390275^Y
KEGG	C08572^Y
ChEMBL	CHEMBL504329^Y
Jmol-3D images	{{#if:O=C\1O[C@H](/C=C/1CCCCCCCCCCCC[C@@H](O)[C@@H]3O[C@@H]([C@@H]2O[C@H](CC2)[C@@H](OC(=O)C)CCCCCCCCCC)CC3)C\|Image 1
SMILES O=C\1O[C@H](/C=C/1CCCCCCCCCCCC[C@@H](O)[C@@H]3O[C@@H]([C@@H]2O[C@H](CC2)[C@@H](OC(=O)C)CCCCCCCCCC)CC3)C
InChI InChI=1S/C39H68O7/c1-4-5-6-7-8-15-18-21-24-35(44-31(3)40)36-27-28-38(46-36)37-26-25-34(45-37)33(41)23-20-17-14-12-10-9-11-13-16-19-22-32-29-30(2)43-39(32)42/h29-30,33-38,41H,4-28H2,1-3H3/t30-,33+,34+,35-,36+,37+,38+/m0/s1^Y Key: JQOYPOSGHDJFLI-AVNCTIOFSA-N^Y InChI=1/C39H68O7/c1-4-5-6-7-8-15-18-21-24-35(44-31(3)40)36-27-28-38(46-36)37-26-25-34(45-37)33(41)23-20-17-14-12-10-9-11-13-16-19-22-32-29-30(2)43-39(32)42/h29-30,33-38,41H,4-28H2,1-3H3/t30-,33+,34+,35-,36+,37+,38+/m0/s1 Key: JQOYPOSGHDJFLI-AVNCTIOFBH
Properties
Molecular formula	C₃₉H₆₈O₇
Molar mass	648.95 g mol⁻¹
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Uvaricin is a bis(tetrahydrofuranoid) fatty acid lactone that was first isolated in 1982 from the roots of the Annonaceae Uvaria acuminata.^[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]

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)". Journal of Organic Chemistry 47 (16): 3151–3153. doi:10.1021/jo00137a024.
↑ 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.
↑ Yazbak, A.; Sinha, S. C.; Keinan, E. (1998). "Total Synthesis of Uvaricin". Journal of Organic Chemistry 63 (17): 5863–5868. doi:10.1021/jo980453a. PMID 11672188.
↑ 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.

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