The synthesis and biological evaluation of para-substituted phenolic N-alkyl carbamates as endocannabinoid hydrolyzing enzyme inhibitors

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dc.contributor Aalto-yliopisto fi
dc.contributor Aalto University en
dc.contributor.author Minkkila, Anna
dc.contributor.author Myllymaki, Mikko J.
dc.contributor.author Saario, Susanna M.
dc.contributor.author Castillo-Melendez, Joel A.
dc.contributor.author Koskinen, Ari M.P.
dc.contributor.author Fowler, Christopher J.
dc.contributor.author Leppanen, Jukka
dc.contributor.author Nevalainen, Tapio
dc.date.accessioned 2016-09-23T09:24:42Z
dc.date.issued 2009
dc.identifier.citation Minkkila , A , Myllymaki , M J , Saario , S M , Castillo-Melendez , J A , Koskinen , A M P , Fowler , C J , Leppanen , J & Nevalainen , T 2009 , ' The synthesis and biological evaluation of para-substituted phenolic N-alkyl carbamates as endocannabinoid hydrolyzing enzyme inhibitors ' EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY , vol 44 , no. 7 , pp. 2994-3008 . DOI: 10.1016/j.ejmech.2009.01.007 en
dc.identifier.issn 0223-5234
dc.identifier.other PURE UUID: 7213b964-9680-450a-a28f-d9ddeeba6e7d
dc.identifier.other PURE ITEMURL: https://research.aalto.fi/en/publications/the-synthesis-and-biological-evaluation-of-parasubstituted-phenolic-nalkyl-carbamates-as-endocannabinoid-hydrolyzing-enzyme-inhibitors(7213b964-9680-450a-a28f-d9ddeeba6e7d).html
dc.identifier.other PURE FILEURL: https://research.aalto.fi/files/7159754/ms140.pdf
dc.identifier.uri https://aaltodoc.aalto.fi/handle/123456789/22429
dc.description.abstract A series of para-substituted phenolic N-alkyl carbamates were evaluated for their FAAH and MGL inhibitory activities. The compounds were generally selective for FAAH, with IC50 values in the nM range, whereas inhibition of MGL required concentrations three orders of magnitude higher. The most potent compounds, dodecylcarbamic acid 4-(4,5-dihydrothiazol-2-yl)phenyl (12) and 4-(1,2,3-thiadiazol-4-yl)phenyl (26) esters, inhibited FAAH and MGL with IC50 values at the low-nanomolar (IC50s; 0.0063 and 0.012 mM) and the low-micromolar ranges (IC50s; 2.1 and 1.0 mM), respectively. Compound 26 also inhibited both FAAH-dependent AEA uptake and AEA hydrolysis (IC50; 0.082 mM) by intact RBL2H3 cells, and could also reduce 2-AG hydrolysis by these cells at concentrations 0.030 mM. en
dc.format.extent 2994-3008
dc.format.mimetype application/pdf
dc.language.iso en en
dc.relation.ispartofseries EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY en
dc.relation.ispartofseries Volume 44, issue 7 en
dc.rights openAccess en
dc.subject.other 116 Chemical sciences en
dc.title The synthesis and biological evaluation of para-substituted phenolic N-alkyl carbamates as endocannabinoid hydrolyzing enzyme inhibitors en
dc.type A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä fi
dc.description.version Peer reviewed en
dc.contributor.department School services, CHEM
dc.contributor.department Department of Chemistry
dc.contributor.department Department of Chemistry and Materials Science
dc.contributor.department Organic Chemistry
dc.subject.keyword endocannabinoid
dc.subject.keyword N-Arachidonoylethanolamine (AEA)
dc.subject.keyword 2-Arachidonoylglycerol (2-AG)
dc.subject.keyword fatty acid amide hydrolase (FAAH)
dc.subject.keyword Monoglyceride lipase
dc.subject.keyword 116 Chemical sciences
dc.identifier.urn URN:NBN:fi:aalto-201609234432
dc.identifier.doi 10.1016/j.ejmech.2009.01.007
dc.type.version acceptedVersion


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