Uvaricin

Chembox new
Name = (+)-Uvaricin
ImageFile = Uvaricin.svg
ImageSize = 280
IUPACName = 3-(13-(5′-(1-(acetyloxy)undecyl)octahydro(2,2′-bifuran) -5-yl)-13-hydroxytridecyl)-5-methyl-2(5"H")-Furanone
Section1 = Chembox Identifiers
CASNo = 82064-83-3
KEGG = C08572
PubChem = 441645
SMILES =
Section2 = Chembox Properties
C=39|H=68|O=7
Appearance =
Density =
MeltingPt =
BoilingPt =
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Section3 = Chembox Hazards
MainHazards =
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Uvaricin is a bis(tetrahydrofuranoid) fatty acid lactone that was first isolated in 1982 from the roots of "Uvaria accuminata".cite journal
author = Jolad, S. D.; Hoffmann, J. J.; Schram, K. H.; Cole, J. R.; Tempesta, M. S.; Kriek, G. R.; Bates, R. B.
title = Uvaricin, a new antitumor agent from Uvaria accuminata (Annonaceae)
year = 1982
journal = The Journal of Organic Chemistry
volume = 47
issue = 16
pages = 3151–3153
doi = 10.1021/jo00137a024
url = http://pubs.acs.org/cgi-bin/abstract.cgi/joceah/1982/47/i16/f-pdf/f_jo00137a024.pdf?sessid=6006l3] 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.cite journal
author = Zafra-Polo, M. C.; González, M. C.; Estornell, E.; Sahpaz, S.; Cortes, D.
year = 1996
title = Acetogenins from annonaceae, inhibitors of mitochondrial complex I
journal = Phytochemistry
volume = 42
issue = 2
pages = 253–271
doi = 10.1016/0031-9422(95)00836-5
url = http://linkinghub.elsevier.com/retrieve/pii/0031942295008365] A method to synthesize uvaricin was first published in 1998,cite journal
author = Yazbak, A.; Sinha, S. C.; Keinan, E.
title = Total Synthesis of Uvaricin
year = 1998
journal = J. Org. Chem
volume = 63
pages = 5863–5868
doi = 10.1021/jo980453a
url = http://www.technion.ac.il/~keinanj/pub/92.pdf] and an improved stereoselective synthesis published in 2001.cite journal
author = Burke, S. D.; Jiang, L.
title =Formal Synthesis of Uvaricin via Palladium-Mediated Double Cyclization
year = 2001
journal = ORGANIC LETTERS
volume = 3
pages = 1953–1956
doi = 10.1021/ol0160304
url = http://pubs.acs.org/cgi-bin/abstract.cgi/orlef7/2001/3/i12/abs/ol0160304.html]

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