Chiral 3-(4,5-dihydrooxazol-2-yl)phenyl alkylcarbamates as novel FAAH inhibitors: Insight into FAAH enantioselectivity by molecular docking and interaction fields

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dc.contributor Aalto-yliopisto fi
dc.contributor Aalto University en
dc.contributor.author Myllymaki, Mikko J.
dc.contributor.author Kasnanen, Heikki
dc.contributor.author Kataja, Antti O.
dc.contributor.author Lahtela-Kakkonen, Maija
dc.contributor.author Saario, Susanna M.
dc.contributor.author Poso, Antti
dc.contributor.author Koskinen, Ari M.P.
dc.date.accessioned 2016-09-23T09:25:40Z
dc.date.issued 2009
dc.identifier.citation Myllymaki , M J , Kasnanen , H , Kataja , A O , Lahtela-Kakkonen , M , Saario , S M , Poso , A & Koskinen , A M P 2009 , ' Chiral 3-(4,5-dihydrooxazol-2-yl)phenyl alkylcarbamates as novel FAAH inhibitors: Insight into FAAH enantioselectivity by molecular docking and interaction fields ' EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY , vol 44 , no. 10 , pp. 4179-4191 . DOI: 10.1016/j.ejmech.2009.05.012 en
dc.identifier.issn 0223-5234
dc.identifier.other PURE UUID: 8e2297c5-d6f6-4931-a126-dd166aeb3d7d
dc.identifier.other PURE ITEMURL: https://research.aalto.fi/en/publications/chiral-345dihydrooxazol2ylphenyl-alkylcarbamates-as-novel-faah-inhibitors-insight-into-faah-enantioselectivity-by-molecular-docking-and-interaction-fields(8e2297c5-d6f6-4931-a126-dd166aeb3d7d).html
dc.identifier.other PURE FILEURL: https://research.aalto.fi/files/7159863/ms142.pdf
dc.identifier.uri https://aaltodoc.aalto.fi/handle/123456789/22444
dc.description.abstract Fatty acid amide hydrolase (FAAH) and monoglyceride lipase (MGL) are the main enzymes responsible for the hydrolysis of endogenous cannabinoids N-arachidonoylethanolamide (AEA) and 2-arachidonoylglycerol (2-AG), respectively. Phenyl alkylcarbamates are FAAH inhibitors with anxiolytic and analgesic activities in vivo. Herein we present for the first time the synthesis and biological evaluation of a series of chiral 3-(2-oxazoline)-phenyl N-alkylcarbamates as FAAH inhibitors. Furthermore, the structural background of chirality on the FAAH inhibition is explored by analyzing the protein–ligand interactions. Remarkably, 10-fold difference in potency was observed for (R)- and (S)-derivatives of 3-(5-methyl-4,5-dihydrooxazol-2-yl)phenyl cyclohexylcarbamate (6a vs. 6b). Molecular modelling indicated an important interaction between the oxazoline nitrogen and FAAH active site. en
dc.format.extent 4179-4191
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 10 en
dc.rights openAccess en
dc.subject.other 116 Chemical sciences en
dc.title Chiral 3-(4,5-dihydrooxazol-2-yl)phenyl alkylcarbamates as novel FAAH inhibitors: Insight into FAAH enantioselectivity by molecular docking and interaction fields en
dc.type A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä fi
dc.description.version Peer reviewed en
dc.contributor.department Department of Chemistry en
dc.subject.keyword FAAH inhibitor
dc.subject.keyword fatty acid amide hydrolase (FAAH)
dc.subject.keyword carbamate
dc.subject.keyword enantiomeric pair
dc.subject.keyword 116 Chemical sciences
dc.identifier.urn URN:NBN:fi:aalto-201609234447
dc.identifier.doi 10.1016/j.ejmech.2009.05.012
dc.type.version acceptedVersion


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