| 词条 | Uvaricin |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470627309 | 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(5H)-Furanone |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 390275 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 504329 | 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 | InChIKey = JQOYPOSGHDJFLI-AVNCTIOFBH | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = JQOYPOSGHDJFLI-AVNCTIOFSA-N | CASNo_Ref = {{cascite|changed|??}} | CASNo = 82064-83-3 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C08572 | PubChem = 441645 | 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 }} |Section2={{Chembox Properties | C=39 | H=68 | O=7 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}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 known example in a class of compounds 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] References1. ^{{cite journal |author1=Jolad, S. D. |author2=Hoffmann, J. J. |author3=Schram, K. H. |author4=Cole, J. R. |author5=Tempesta, M. S. |author6=Kriek, G. R. |author7=Bates, R. B. | title = Uvaricin, a New Antitumor Agent from Uvaria accuminata (Annonaceae) | journal = Journal of Organic Chemistry | year = 1982 | volume = 47 | issue = 16 | pages = 3151–3153 | doi = 10.1021/jo00137a024 }} {{organic-compound-stub}}2. ^{{cite journal |author1=Zafra-Polo, M. C. |author2=González, M. C. |author3=Estornell, E. |author4=Sahpaz, S. |author5=Cortes, D. | title = Acetogenins from Annonaceae, Inhibitors of Mitochondrial Complex I | journal = Phytochemistry | year = 1996 | volume = 42 | issue = 2 | pages = 253–271 | doi = 10.1016/0031-9422(95)00836-5 | pmid = 8688168 }} 3. ^{{cite journal | author1 = Yazbak, A. | author2 = Sinha, S. C. | author3 = Keinan, E. | title = Total Synthesis of Uvaricin | journal = Journal of Organic Chemistry | year = 1998 | volume = 63 | issue = 17 | pages = 5863–5868 | doi = 10.1021/jo980453a | url = http://www.technion.ac.il/~keinanj/pub/92.pdf | pmid = 11672188 | access-date = 2008-07-14 | archive-url = https://web.archive.org/web/20110717211654/http://www.technion.ac.il/~keinanj/pub/92.pdf | archive-date = 2011-07-17 | dead-url = yes | df = }} 4. ^{{cite journal |author1=Burke, S. D. |author2=Jiang, L. | title = Formal Synthesis of Uvaricin via Palladium-Mediated Double Cyclization | journal = Organic Letters | year = 2001 | volume = 3 | issue = 12 | pages = 1953–1956 | doi = 10.1021/ol0160304 | pmid = 11405753 }} 4 : Acetate esters|Tetrahydrofurans|Furanones|Polyketides |
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