| Revision as of 17:53, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 428800534 of page Spirotryprostatin_A for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 16:58, 16 July 2021 edit JJMC89 bot III (talk | contribs)Bots, Administrators3,681,570 editsm Moving Category:Heterocyclic compounds (3 rings) to Category:Heterocyclic compounds with 3 rings per Misplaced Pages:Categories for discussion/Log/2021 June 24#Category:Heterocyclic compounds (1 ring) |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 265848044 |
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| Name = '''Spirotryprostatin A''' |
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| verifiedrevid = 470470237 |
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| Name = Spirotryprostatin A |
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| ImageFile = SpirotryprostatinA.png |
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| ImageFile = SpirotryprostatinA.png |
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| ImageSize = 200px |
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| ImageName = Spirotryptostatin A |
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| ImageName = Spirotryptostatin A |
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| PIN = (2''S'',3''S'',5a''S'',10a''S'')-2′-Hydroxy-6′-methoxy-3-(2-methylprop-1-en-1-yl)-1,5a,6,7,8,10,10a-hexahydro-3''H'',5''H'',10''H''-spiropyrazine-2,3′-indole]-5,10-dione |
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| Section2 = {{Chembox Properties |
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|Section1 = {{Chembox Identifiers |
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| CASNo = 182234-25-9 |
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| CASNo_Ref = {{Cascite|changed|}} |
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| ChEMBL = 549475 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 8583811 |
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| PubChem = 10408374 |
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| SMILES = CC(=C12(C3N1C(=O)4CCCN4C3=O)C5=C(C=C(C=C5)OC)NC2=O)C |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C22H25N3O4/c1-12(2)9-18-22(14-7-6-13(29-3)10-15(14)23-21(22)28)11-17-19(26)24-8-4-5-16(24)20(27)25(17)18/h6-7,9-10,16-18H,4-5,8,11H2,1-3H3,(H,23,28)/t16-,17-,18-,22-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = MQJKGSIAJNXSCM-ORGXJRBJSA-N |
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}} |
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|Section2 = {{Chembox Properties |
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| Formula = C<sub>22</sub>H<sub>25</sub>N<sub>3</sub>O<sub>4</sub> |
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| Formula = C<sub>22</sub>H<sub>25</sub>N<sub>3</sub>O<sub>4</sub> |
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| MolarMass = 395.43 g/mol}} |
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| MolarMass = 395.43 g/mol}} |
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'''Spirotryprostatin A''' is an ] ] from the ] class of natural products found in the '']'' fungus. Spirotryprostatin A and several other indolic alkaloids (including ], as well as other tryprostatins and cyclotryprostatins) have been found to have anti-] properties, and as such they have become of great interest as anti-] drugs.<ref>{{Cite journal | title = 2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products | author = Borthwick AD | journal = Chemical Reviews | year = 2012 | volume = 112 | issue = 7 | pages = 3641–3716 | doi = 10.1021/cr200398y | pmid = 22575049}}</ref> Because of this, the ] of these compounds is a major pursuit of organic chemists, and a number of different syntheses have been published in the chemical literature. |
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One such total synthesis was published in 1999, which showed that the isopropylidene side chain was not necessary to the biological activity of the compound, leading to a number of new theorized analogues.<ref name=Edmondson>{{cite journal | author=Edmondson, S| title=Total Synthesis of Spirotryprostatin A, Leading to the Discovery of Some Biologically Promising Analogues | journal=J. Am. Chem. Soc. | year=1999 | pages=2147–2155 | volume=121 | issue=10|doi=10.1021/ja983788i|display-authors=etal}}</ref> |
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== References == |
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