“Voacamine”的意思、由来-开放百科全书

{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477868390
| IUPAC_name = (6R,6aR,7R,11S)-methyl 7-ethyl-3-((2R,6S,8R,14S,E)-5-ethylidene-14-(methoxycarbonyl)-3-methyl-2,3,4,5,6,7,8,9-octahydro-1H-2,6-methanoazecino[5,4-b]indol-8-yl)-2-methoxy-6,6a,7,8,9,10,12,13-octahydro-5H-6,9-methanopyrido[1',2':1,2]azepino[4,5-b]indole-6-carboxylate
| image = Voacamine chemical structure.png
| width = 240
| tradename =
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 3371-85-5
| PubChem = 11953931
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB04877
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 30808559
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 445022
| C=43 | H=52 | N=4 | O=5
| smiles = CCC1CC2CC3(C1N(C2)CCC4=C3NC5=CC(=C(C=C45)OC)C6CC\\7C(C(CC8=C6NC9=CC=CC=C89)N(C/C7=C/C)C)C(=O)OC)C(=O)OC
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C43H52N4O5/c1-7-24-15-23-20-43(42(49)52-6)39-27(13-14-47(21-23)40(24)43)29-19-36(50-4)30(17-34(29)45-39)31-16-28-25(8-2)22-46(3)35(37(28)41(48)51-5)18-32-26-11-9-10-12-33(26)44-38(31)32/h8-12,17,19,23-24,28,31,35,37,40,44-45H,7,13-16,18,20-22H2,1-6H3/b25-8-/t23-,24+,28-,31+,35-,37-,40-,43-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = VCMIRXRRQJNZJT-XBBWQDJOSA-N
}}

Voacamine, also known under the older names voacanginine and vocamine, is a naturally occurring dimeric indole alkaloid of the secologanin type, found in a number of plants, including Voacanga africana.

It is approved for use as an antimalarial drug in several African countries.^[1]

Chemical structure

There is considerable confusion about the absolute stereochemical configuration of voacamine and the originally published absolute structure had to be later revised.^[3]^[4]

References

1. ^{{cite web | url = https://www.drugbank.ca/drugs/DB04877 | title = Voacamine | work = DrugBank | publisher = Canadian Institutes of Health Research }}
2. ^{{Cite journal|date=2011-04-01|title=Discovery of indole alkaloids with cannabinoid CB1 receptor antagonistic activity|url=https://www.sciencedirect.com/science/article/pii/S0960894X11002204|journal=Bioorganic & Medicinal Chemistry Letters|language=en|volume=21|issue=7|pages=1962–1964|doi=10.1016/j.bmcl.2011.02.036|pmid=21376588|issn=0960-894X|last1=Kitajima|first1=Mariko|last2=Iwai|first2=Masumi|last3=Kikura-Hanajiri|first3=Ruri|last4=Goda|first4=Yukihiro|last5=Iida|first5=Mitsuru|last6=Yabushita|first6=Hisatoshi|last7=Takayama|first7=Hiromitsu}}
3. ^{{cite journal|author1=James P. Kutney |author2=Richard T. Brown |author3=Edward Piers |last-author-amp=yes | year = 1966| title = The absolute configuration of the iboga alkaloids| journal = Can. J. Chem.| volume = 44| issue = 5| pages = 637–639| pmid =| doi = 10.1139/v66-087| url = http://rparticle.web-p.cisti.nrc.ca/rparticle/AbstractTemplateServlet?calyLang=eng&journal=cjc&volume=44&year=1966&issue=5&msno=v66-087}}
4. ^{{cite journal| author = J. P. Kutney, Kaoru Fuji, Adi M. Treasurywala, Jose Fayos, Jon Clardy, A. Ian Scott, C. C. Wei| year = 1973| title = Structure and Absolute Configuration of (+)-Coronaridine Hydrobromide. A Comment on the Absolute Configuration of the Iboga Alkaloids| journal = J. Am. Chem. Soc.| volume = 95| issue = 16| pages = 5407–5409| pmid =| doi = 10.1021/ja00797a049}}