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Revision as of 22:37, 31 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors or [[user talk:CheMoB← Previous edit Latest revision as of 03:22, 15 April 2024 edit undoJamesray1 (talk | contribs)169 editsNo edit summaryTags: Mobile edit Mobile web edit 
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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
⚫ | verifiedrevid = 443861106
| Watchedfields = changed
⚫ | IUPAC_name = 6,7-dimethoxy-3-(6-methyl-5,6,7,8-tetrahydrodioxoloisoquinolin-5-yl)-2-benzofuran-1(3''H'')-one
⚫ | verifiedrevid = 447739670
⚫ | image = Hydrastine.PNG
⚫ | IUPAC_name = 6,7-Dimethoxy-3-(6-methyl-5,6,7,8-tetrahydrodioxoloisoquinolin-5-yl)-2-benzofuran-1(3''H'')-one
⚫ | image = Hydrastine.svg
| width = 150 | width = 150


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| pregnancy_category = | pregnancy_category =
| legal_status = | legal_status =
| routes_of_administration = | routes_of_administration =


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
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<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 118-08-1 | CAS_number = 118-08-1
| ATC_prefix = none | ATC_prefix = none
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank =
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 497942
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 171234 | ChemSpiderID = 171234
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<!--Chemical data--> <!--Chemical data-->
| C=21 | H=21 | N=1 | O=6 | C=21 | H=21 | N=1 | O=6
| molecular_weight = 383.395 g/mol
| smiles = O=C2O(c1ccc(OC)c(OC)c12)5N(C)CCc4c5cc3OCOc3c4 | smiles = O=C2O(c1ccc(OC)c(OC)c12)5N(C)CCc4c5cc3OCOc3c4
| InChI = 1/C21H21NO6/c1-22-7-6-11-8-15-16(27-10-26-15)9-13(11)18(22)19-12-4-5-14(24-2)20(25-3)17(12)21(23)28-19/h4-5,8-9,18-19H,6-7,10H2,1-3H3/t18-,19+/m1/s1
| InChIKey = JZUTXVTYJDCMDU-MOPGFXCFBB
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C21H21NO6/c1-22-7-6-11-8-15-16(27-10-26-15)9-13(11)18(22)19-12-4-5-14(24-2)20(25-3)17(12)21(23)28-19/h4-5,8-9,18-19H,6-7,10H2,1-3H3/t18-,19+/m1/s1 | StdInChI = 1S/C21H21NO6/c1-22-7-6-11-8-15-16(27-10-26-15)9-13(11)18(22)19-12-4-5-14(24-2)20(25-3)17(12)21(23)28-19/h4-5,8-9,18-19H,6-7,10H2,1-3H3/t18-,19+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JZUTXVTYJDCMDU-MOPGFXCFSA-N | StdInChIKey = JZUTXVTYJDCMDU-MOPGFXCFSA-N
| melting_point = 132
}} }}


'''Hydrastine''' is a natural ] which was discovered in 1851 by ].<ref>{{citation|journal=American Journal of Pharmacy|year=1851|page=112}}</ref> Hydrolysis of hydrastine yields ], which was patented by ] as a ] drug<ref>{{citation|title=Römpp CD|publisher=Georg Thieme Verlag|year=2006}}</ref> during the 1910s. '''Hydrastine''' is an ] ] which was discovered in 1851 by ].<ref>{{cite journal | vauthors = Perrins JD | title = On Hydrastine, an Alkaloid Occurring in Hydrastis Canadensis. | date = July 1862 | journal = Pharmaceutical Journal: A Weekly Record of Pharmacy and Allied Sciences|url=https://books.google.com/books?id=IusKAAAAYAAJ&pg=PA547|year=1862|publisher=J. Churchill|pages=547–}}</ref> ] of hydrastine yields ], which was patented by ] as a ] drug<ref>{{citation|title=Römpp CD|publisher=Georg Thieme Verlag|year=2006}}</ref> during the 1910s. It is present in '']'' (thus the name) and other plants of the family ].


==Total synthesis==
It is naturally present in '']'' (thus the name) and other plants of the ] family.


The first attempt for the ] of hydrastine was reported by ] and co-workers<ref name="HopePyman1931">{{cite journal| vauthors = Hope E, Pyman FL, Remfry FG, Robinson R |title=XXXI.—A synthesis of hydrastine. Part I|journal=J. Chem. Soc.|year=1931|pages=236–247|issn=0368-1769| doi=10.1039/JR9310000236}}</ref> in 1931. Following studies<ref name="HaworthPinder1950">{{cite journal| vauthors = Haworth RD, Pinder AR, Robinson R |title=Synthesis of Hydrastine|journal=Nature|volume=165|issue=4196|year=1950|pages=529|issn=0028-0836|doi=10.1038/165529a0|bibcode=1950Natur.165..529H|s2cid=4198366|doi-access=free}}</ref><ref name="HaworthPinder1950B">{{cite journal| vauthors = Haworth RD, Pinder AR |title=360. A new route to the phthalide-isoquinoline bases, and a synthesis of (–)-hydrastine|journal=J. Chem. Soc.|year=1950|pages=1776–1780|issn=0368-1769|doi=10.1039/JR9500001776}}</ref> where the synthesis of the key lactonic amide intermediate (structure 4 in figure) was the most troublesome, the major breakthrough was achieved in 1981 when J. R. Falck and co-workers<ref name="FalckManna1981">{{cite journal| vauthors = Falck JR, Manna S |author1-link=John R. Falck |title=An intramolecular passerini reaction: Synthesis of hydrastine.|journal=Tetrahedron Letters|volume=22|issue=7|year=1981|pages=619–620|issn=0040-4039|doi=10.1016/S0040-4039(01)92504-3}}</ref> reported a four-step total synthesis of hydrastine from simple starting materials. The key step in the Falck synthesis was using a ] to construct the lactonic amide intermediate 4.
⚫ ==References==
:]
{{reflist}}
Starting from a simple phenylbromide variant 1, alkylation reaction with lithium methylisocyanide gives the ] intermediate 2. Reacting isocyanide intermediate 2 with opianic acid 3 initiated the intramolecular Passerini reaction to give the key lactonic amide intermediate 4. The tetrahydro-isoquinolin ring was formed by first a ring-closure reaction under dehydration conditions using ] and then a catalyzed hydrogenation using PtO2 as the catalyst. Finally, hydrastine was synthesized by installing the N-methyl group via ] reaction with ].


== See also ==
⚫ ]
* ] (very similar in structure)
]
]
]
]


⚫ == References ==
{{Reflist|2}}


== External links ==
{{Blood-drug-stub}}
* {{cite EB1911|wstitle=Hydrastine |volume=14|page=34}}
{{Biochem-stub}}


{{GABAergics}}
]

]
]
⚫ ]
]