{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,1]],"date-time":"2026-07-01T22:15:18Z","timestamp":1782944118150,"version":"3.54.5"},"reference-count":64,"publisher":"Royal Society of Chemistry (RSC)","issue":"37","license":[{"start":{"date-parts":[[2024,9,4]],"date-time":"2024-09-04T00:00:00Z","timestamp":1725408000000},"content-version":"am","delay-in-days":612,"URL":"http:\/\/rsc.li\/journals-terms-of-use"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["GRK 2515"],"award-info":[{"award-number":["GRK 2515"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["rsc.org"],"crossmark-restriction":true},"short-container-title":["Org. Biomol. Chem."],"abstract":"<jats:p>Nucleophilic opening of aryloxiranes with benzylpiperidine and subsequent rearrangement under Mitsunobu conditions led regioselectively to \u03b1-aryl-\u03b2-piperidinoalcohols and -amines. Amino-ifenprodil and indazole bioisosteres show high GluN2B affinity.<\/jats:p>","DOI":"10.1039\/d3ob01208e","type":"journal-article","created":{"date-parts":[[2023,9,4]],"date-time":"2023-09-04T13:21:41Z","timestamp":1693833701000},"page":"7616-7638","update-policy":"https:\/\/doi.org\/10.1039\/rsc_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Negative allosteric modulators of NMDA receptors with GluN2B subunit: synthesis of \u03b2-aminoalcohols by epoxide opening and subsequent rearrangement"],"prefix":"10.1039","volume":"21","author":[{"given":"Marvin","family":"Korff","sequence":"first","affiliation":[{"name":"Universit\u00e4t M\u00fcnster, Institut f\u00fcr Pharmazeutische und Medizinische Chemie, Corrensstr. 48, D-48149 M\u00fcnster, Germany"},{"name":"Universit\u00e4t M\u00fcnster, GRK 2515, Chemical biology of ion channels (Chembion), Corrensstra\u00dfe 48, D-48149 M\u00fcnster, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Judith","family":"L\u00fcken","sequence":"additional","affiliation":[{"name":"Universit\u00e4t M\u00fcnster, Institut f\u00fcr Pharmazeutische und Medizinische Chemie, Corrensstr. 48, D-48149 M\u00fcnster, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Judith","family":"Schmidt","sequence":"additional","affiliation":[{"name":"Universit\u00e4t M\u00fcnster, Institut f\u00fcr Pharmazeutische und Medizinische Chemie, Corrensstr. 48, D-48149 M\u00fcnster, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dirk","family":"Schepmann","sequence":"additional","affiliation":[{"name":"Universit\u00e4t M\u00fcnster, Institut f\u00fcr Pharmazeutische und Medizinische Chemie, Corrensstr. 48, D-48149 M\u00fcnster, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3952-320X","authenticated-orcid":false,"given":"Gunnar","family":"Goerges","sequence":"additional","affiliation":[{"name":"University Hospital M\u00fcnster, Cellular Electrophysiology and Molecular Biology, Institute for Genetics of Heart Diseases (IfGH), Department of Cardiovascular Medicine, Robert-Koch-Str. 45, D-48149 M\u00fcnster, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nadine","family":"Ritter","sequence":"additional","affiliation":[{"name":"University Hospital M\u00fcnster, Cellular Electrophysiology and Molecular Biology, Institute for Genetics of Heart Diseases (IfGH), Department of Cardiovascular Medicine, Robert-Koch-Str. 45, D-48149 M\u00fcnster, Germany"},{"name":"Universit\u00e4t M\u00fcnster, GRK 2515, Chemical biology of ion channels (Chembion), Corrensstra\u00dfe 48, D-48149 M\u00fcnster, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paul","family":"Disse","sequence":"additional","affiliation":[{"name":"University Hospital M\u00fcnster, Cellular Electrophysiology and Molecular Biology, Institute for Genetics of Heart Diseases (IfGH), Department of Cardiovascular Medicine, Robert-Koch-Str. 45, D-48149 M\u00fcnster, Germany"},{"name":"Universit\u00e4t M\u00fcnster, GRK 2515, Chemical biology of ion channels (Chembion), Corrensstra\u00dfe 48, D-48149 M\u00fcnster, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Julian A.","family":"Schreiber","sequence":"additional","affiliation":[{"name":"Universit\u00e4t M\u00fcnster, Institut f\u00fcr Pharmazeutische und Medizinische Chemie, Corrensstr. 48, D-48149 M\u00fcnster, Germany"},{"name":"University Hospital M\u00fcnster, Cellular Electrophysiology and Molecular Biology, Institute for Genetics of Heart Diseases (IfGH), Department of Cardiovascular Medicine, Robert-Koch-Str. 45, D-48149 M\u00fcnster, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Guiscard","family":"Seebohm","sequence":"additional","affiliation":[{"name":"University Hospital M\u00fcnster, Cellular Electrophysiology and Molecular Biology, Institute for Genetics of Heart Diseases (IfGH), Department of Cardiovascular Medicine, Robert-Koch-Str. 45, D-48149 M\u00fcnster, Germany"},{"name":"Universit\u00e4t M\u00fcnster, GRK 2515, Chemical biology of ion channels (Chembion), Corrensstra\u00dfe 48, D-48149 M\u00fcnster, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9030-8417","authenticated-orcid":false,"given":"Bernhard","family":"W\u00fcnsch","sequence":"additional","affiliation":[{"name":"Universit\u00e4t M\u00fcnster, Institut f\u00fcr Pharmazeutische und Medizinische Chemie, Corrensstr. 48, D-48149 M\u00fcnster, Germany"},{"name":"Universit\u00e4t M\u00fcnster, GRK 2515, Chemical biology of ion channels (Chembion), Corrensstra\u00dfe 48, D-48149 M\u00fcnster, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"292","published-online":{"date-parts":[[2023]]},"reference":[{"issue":"1","key":"D3OB01208E\/cit1\/1","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1016\/j.neuropharm.2008.06.063","volume":"56","author":"Collingridge","year":"2009","journal-title":"Neuropharmacology"},{"issue":"1","key":"D3OB01208E\/cit2\/1","first-page":"7","volume":"51","author":"Dingledine","year":"1999","journal-title":"Pharmacol. Rev."},{"issue":"4","key":"D3OB01208E\/cit3\/1","doi-asserted-by":"crossref","first-page":"159","DOI":"10.1002\/(SICI)1615-1003(200005)29:3<159::AID-PAUZ159>3.0.CO;2-2","volume":"29","author":"Stark","year":"2000","journal-title":"Pharm. Unserer Zeit"},{"issue":"4","key":"D3OB01208E\/cit4\/1","doi-asserted-by":"crossref","first-page":"298","DOI":"10.1124\/pharmrev.120.000131","volume":"73","author":"Hansen","year":"2021","journal-title":"Pharmacol. Rev."},{"issue":"8","key":"D3OB01208E\/cit5\/1","doi-asserted-by":"crossref","first-page":"1081","DOI":"10.1085\/jgp.201812032","volume":"150","author":"Hansen","year":"2018","journal-title":"J. Gen. Physiol."},{"key":"D3OB01208E\/cit6\/1","doi-asserted-by":"crossref","first-page":"156","DOI":"10.1038\/349156a0","volume":"349","author":"Bashir","year":"1991","journal-title":"Nature"},{"issue":"6149","key":"D3OB01208E\/cit7\/1","doi-asserted-by":"crossref","first-page":"649","DOI":"10.1038\/330649a0","volume":"330","author":"Artola","year":"1987","journal-title":"Nature"},{"issue":"2","key":"D3OB01208E\/cit8\/1","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1007\/s40263-015-0225-3","volume":"29","author":"Jia","year":"2015","journal-title":"CNS Drugs"},{"issue":"1","key":"D3OB01208E\/cit9\/1","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1016\/j.coph.2006.08.011","volume":"7","author":"Paoletti","year":"2007","journal-title":"Curr. Opin. Pharmacol."},{"key":"D3OB01208E\/cit10\/1","doi-asserted-by":"crossref","first-page":"405","DOI":"10.1124\/pr.109.002451","volume":"62","author":"Traynelis","year":"2010","journal-title":"Pharmacol. Rev."},{"issue":"6","key":"D3OB01208E\/cit11\/1","doi-asserted-by":"crossref","first-page":"383","DOI":"10.1038\/nrn3504","volume":"14","author":"Paoletti","year":"2013","journal-title":"Nat. Rev. Neurosci."},{"issue":"19","key":"D3OB01208E\/cit12\/1","doi-asserted-by":"crossref","first-page":"11423","DOI":"10.3390\/ijms231911423","volume":"23","author":"Samojedny","year":"2022","journal-title":"Int. J. Mol. Sci."},{"issue":"3","key":"D3OB01208E\/cit13\/1","doi-asserted-by":"crossref","first-page":"454","DOI":"10.1016\/j.drudis.2016.01.016","volume":"21","author":"Gerhard","year":"2016","journal-title":"Drug Discovery Today"},{"issue":"1","key":"D3OB01208E\/cit14\/1","doi-asserted-by":"crossref","first-page":"259","DOI":"10.1002\/med.21817","volume":"42","author":"Tuo","year":"2022","journal-title":"Med. Res. Rev."},{"issue":"1","key":"D3OB01208E\/cit15\/1","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1186\/s13041-018-0357-8","volume":"11","author":"Wu","year":"2018","journal-title":"Mol. Brain"},{"issue":"2","key":"D3OB01208E\/cit16\/1","doi-asserted-by":"crossref","first-page":"e239","DOI":"10.1016\/j.bja.2018.08.025","volume":"123","author":"Zhou","year":"2019","journal-title":"Br. J. Anaesth."},{"issue":"8","key":"D3OB01208E\/cit17\/1","doi-asserted-by":"crossref","first-page":"485","DOI":"10.1038\/nrn.2016.68","volume":"17","author":"Bliss","year":"2016","journal-title":"Nat. Rev. Neurosci."},{"key":"D3OB01208E\/cit18\/1","doi-asserted-by":"crossref","first-page":"42","DOI":"10.1111\/j.1749-6632.1999.tb07979.x","volume":"890","author":"Merchant","year":"1999","journal-title":"Ann. N. Y. Acad. Sci."},{"issue":"4","key":"D3OB01208E\/cit19\/1","doi-asserted-by":"crossref","first-page":"913","DOI":"10.1111\/j.1471-4159.2004.02548.x","volume":"90","author":"Hynd","year":"2004","journal-title":"J. Neurochem."},{"key":"D3OB01208E\/cit20\/1","doi-asserted-by":"crossref","first-page":"43","DOI":"10.3389\/fnins.2019.00043","volume":"13","author":"Liu","year":"2019","journal-title":"Front. Neurosci."},{"key":"D3OB01208E\/cit21\/1","first-page":"165","volume":"8","author":"Gan","year":"2014","journal-title":"Drug Des., Dev. Ther."},{"issue":"18","key":"D3OB01208E\/cit22\/1","doi-asserted-by":"crossref","first-page":"4391","DOI":"10.3390\/ijms20184391","volume":"20","author":"Zhang","year":"2019","journal-title":"Int. J. Mol. Sci."},{"key":"D3OB01208E\/cit23\/1","doi-asserted-by":"crossref","first-page":"249","DOI":"10.1038\/nature10180","volume":"475","author":"Karakas","year":"2011","journal-title":"Nature"},{"key":"D3OB01208E\/cit24\/1","doi-asserted-by":"crossref","first-page":"992","DOI":"10.1126\/science.1251915","volume":"344","author":"Karakas","year":"2014","journal-title":"Science"},{"key":"D3OB01208E\/cit25\/1","doi-asserted-by":"crossref","first-page":"321","DOI":"10.1038\/s41467-019-08291-1","volume":"10","author":"Regan","year":"2019","journal-title":"Nat. Commun."},{"issue":"5","key":"D3OB01208E\/cit26\/1","doi-asserted-by":"crossref","first-page":"541","DOI":"10.1124\/mol.115.103036","volume":"89","author":"Stroebel","year":"2016","journal-title":"Mol. Pharmacol."},{"key":"D3OB01208E\/cit27\/1","doi-asserted-by":"crossref","first-page":"112447","DOI":"10.1016\/j.ejmech.2020.112447","volume":"200","author":"Liu","year":"2020","journal-title":"Eur. J. Med. Chem."},{"key":"D3OB01208E\/cit28\/1","doi-asserted-by":"crossref","first-page":"1301","DOI":"10.1111\/j.1476-5381.2009.00304.x","volume":"157","author":"Mony","year":"2009","journal-title":"Br. J. Pharmacol."},{"key":"D3OB01208E\/cit29\/1","doi-asserted-by":"crossref","first-page":"4","DOI":"10.1016\/j.neuropharm.2013.01.016","volume":"74","author":"Wyllie","year":"2013","journal-title":"Neuropharmacology"},{"issue":"21","key":"D3OB01208E\/cit30\/1","doi-asserted-by":"crossref","first-page":"5825","DOI":"10.1523\/JNEUROSCI.0577-06.2006","volume":"26","author":"Clarke","year":"2006","journal-title":"J. Neurosci."},{"issue":"8","key":"D3OB01208E\/cit31\/1","doi-asserted-by":"crossref","first-page":"1351","DOI":"10.1111\/j.1460-9568.2011.07628.x","volume":"33","author":"Paoletti","year":"2011","journal-title":"Eur. J. Neurosci."},{"issue":"4","key":"D3OB01208E\/cit32\/1","doi-asserted-by":"crossref","first-page":"255","DOI":"10.1515\/hsz-2022-0229","volume":"404","author":"Bechthold","year":"2023","journal-title":"Biol. Chem."},{"key":"D3OB01208E\/cit33\/1","doi-asserted-by":"crossref","first-page":"8885","DOI":"10.1523\/JNEUROSCI.2476-04.2004","volume":"24","author":"Liu","year":"2004","journal-title":"J. Neurosci."},{"key":"D3OB01208E\/cit34\/1","first-page":"5093048","author":"Baez","year":"2018","journal-title":"Neural Plast."},{"issue":"12","key":"D3OB01208E\/cit35\/1","doi-asserted-by":"crossref","first-page":"2267","DOI":"10.1021\/jo00952a046","volume":"38","author":"Anderson","year":"1973","journal-title":"J. Org. Chem."},{"key":"D3OB01208E\/cit36\/1","author":"Mohan","unstructured":"R. S.Mohan  and  D. L.Whalen"},{"key":"D3OB01208E\/cit37\/1","doi-asserted-by":"crossref","first-page":"1407","DOI":"10.1021\/jo991521b","volume":"65","author":"Mohan","year":"2000","journal-title":"J. Org. Chem."},{"issue":"6","key":"D3OB01208E\/cit38\/1","doi-asserted-by":"crossref","first-page":"823","DOI":"10.1134\/S1070428008060079","volume":"44","author":"Elgendy","year":"2008","journal-title":"Russ. J. Org. Chem."},{"key":"D3OB01208E\/cit39\/1","doi-asserted-by":"crossref","first-page":"133","DOI":"10.1016\/j.forsciint.2004.02.033","volume":"143","author":"Waumans","year":"2004","journal-title":"Forensic Sci. Int."},{"key":"D3OB01208E\/cit40\/1","doi-asserted-by":"crossref","first-page":"5787","DOI":"10.1039\/c3ob41245h","volume":"11","author":"Guo","year":"2013","journal-title":"Org. Biomol. Chem."},{"issue":"4","key":"D3OB01208E\/cit41\/1","doi-asserted-by":"crossref","first-page":"516","DOI":"10.1021\/ja01220a004","volume":"67","author":"Emerson","year":"1945","journal-title":"J. Am. Chem. Soc."},{"issue":"1","key":"D3OB01208E\/cit42\/1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/prac.19713130102","volume":"313","author":"M\u00fcller","year":"1971","journal-title":"J. Prakt. Chem."},{"key":"D3OB01208E\/cit43\/1","doi-asserted-by":"crossref","first-page":"1719","DOI":"10.1071\/CH9721719","volume":"25","author":"Feutrill","year":"1972","journal-title":"Aust. J. Chem."},{"issue":"10","key":"D3OB01208E\/cit44\/1","doi-asserted-by":"crossref","first-page":"2380","DOI":"10.1246\/bcsj.40.2380","volume":"40","author":"Mitsunobu","year":"1967","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"D3OB01208E\/cit45\/1","doi-asserted-by":"crossref","first-page":"670","DOI":"10.1021\/jo00002a033","volume":"56","author":"Freedman","year":"1991","journal-title":"J. Org. Chem."},{"issue":"12","key":"D3OB01208E\/cit46\/1","doi-asserted-by":"crossref","first-page":"1912","DOI":"10.2967\/jnumed.122.263977","volume":"63","author":"Ahmed","year":"2022","journal-title":"J. Nucl. Med."},{"key":"D3OB01208E\/cit47\/1","doi-asserted-by":"crossref","first-page":"11946","DOI":"10.1021\/ja025956j","volume":"124","author":"Lane","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"D3OB01208E\/cit48\/1","doi-asserted-by":"crossref","first-page":"2224","DOI":"10.1002\/cber.18870200227","volume":"20","author":"Gabriel","year":"1887","journal-title":"Chem. Ber."},{"issue":"32","key":"D3OB01208E\/cit49\/1","doi-asserted-by":"crossref","first-page":"9757","DOI":"10.1016\/S0040-4020(01)85541-1","volume":"50","author":"Simon","year":"1994","journal-title":"Tetrahedron"},{"key":"D3OB01208E\/cit50\/1","author":"Pujala","unstructured":"B.Pujala ,  D.Panpatil ,  S.Bernales ,  S.Belmar  and  D. G. A.Ureta"},{"key":"D3OB01208E\/cit51\/1","doi-asserted-by":"crossref","first-page":"637","DOI":"10.1002\/cbic.200301023","volume":"5","author":"B\u00f6hm","year":"2004","journal-title":"ChemBioChem"},{"key":"D3OB01208E\/cit52\/1","doi-asserted-by":"crossref","first-page":"3953","DOI":"10.1016\/j.bmcl.2004.05.053","volume":"14","author":"Barta-Szalai","year":"2004","journal-title":"Bioorg. Med. Chem. Lett."},{"issue":"3","key":"D3OB01208E\/cit53\/1","doi-asserted-by":"crossref","first-page":"603","DOI":"10.1016\/j.jpba.2010.04.014","volume":"53","author":"Schepmann","year":"2010","journal-title":"J. Pharm. Biomed. Anal."},{"issue":"9","key":"D3OB01208E\/cit54\/1","doi-asserted-by":"publisher","first-page":"e2200147","DOI":"10.1002\/ardp.202200147","volume":"355","author":"Markus","year":"2022","journal-title":"Arch. Pharm."},{"issue":"7","key":"D3OB01208E\/cit55\/1","doi-asserted-by":"crossref","first-page":"1844","DOI":"10.1016\/j.bmc.2013.01.038","volume":"21","author":"Meyer","year":"2013","journal-title":"Bioorg. Med. Chem."},{"key":"D3OB01208E\/cit56\/1","doi-asserted-by":"crossref","first-page":"709","DOI":"10.1016\/j.ejmech.2014.06.073","volume":"83","author":"Miyata","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"D3OB01208E\/cit57\/1","doi-asserted-by":"crossref","first-page":"5407","DOI":"10.1039\/C4OB00510D","volume":"12","author":"Hasebein","year":"2014","journal-title":"Org. Biomol. Chem."},{"key":"D3OB01208E\/cit58\/1","doi-asserted-by":"publisher","first-page":"1170","DOI":"10.1021\/acs.jmedchem.0c01912","volume":"64","author":"Bechthold","year":"2021","journal-title":"J. Med. Chem."},{"key":"D3OB01208E\/cit59\/1","doi-asserted-by":"publisher","first-page":"420","DOI":"10.1038\/s42003-019-0645-6","volume":"2","author":"Schreiber","year":"2019","journal-title":"Commun. Biol."},{"key":"D3OB01208E\/cit60\/1","doi-asserted-by":"crossref","first-page":"214","DOI":"10.1016\/j.jpba.2019.04.032","volume":"172","author":"B\u00f6rgel","year":"2019","journal-title":"J. Pharm. Biomed. Anal."},{"key":"D3OB01208E\/cit61\/1","doi-asserted-by":"crossref","first-page":"4115","DOI":"10.1021\/acs.jmedchem.8b00200","volume":"61","author":"Butsch","year":"2018","journal-title":"J. Med. Chem."},{"key":"D3OB01208E\/cit62\/1","doi-asserted-by":"crossref","first-page":"36","DOI":"10.1016\/j.jpba.2014.01.017","volume":"94","author":"Falck","year":"2014","journal-title":"J. Pharm. Biomed. Anal."},{"key":"D3OB01208E\/cit63\/1","doi-asserted-by":"crossref","first-page":"96","DOI":"10.1016\/j.jpba.2013.08.014","volume":"88","author":"Falck","year":"2014","journal-title":"J. Pharm. Biomed. Anal."},{"key":"D3OB01208E\/cit64\/1","author":"Luk","year":"2012","unstructured":"K. C. T.Luk ,  S. M.Lynch ,  C.O'Yang ,  F.Padilla ,  R. C.Schoenfeld ,  A.Sidduri ,  M.Soth ,  C.Wang ,  P. M.Wovkulich  and  X.Zhang ,  Pyrrolopyrazine kinase inhibitors, WO2013030138 (A1) ,  2012"}],"container-title":["Organic &amp; Biomolecular Chemistry"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/pubs.rsc.org\/en\/content\/articlepdf\/2023\/OB\/D3OB01208E","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,7,1]],"date-time":"2026-07-01T21:40:13Z","timestamp":1782942013000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.rsc.org\/ob\/article\/21\/37\/7616-7638\/819851"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023]]},"references-count":64,"journal-issue":{"issue":"37","published-print":{"date-parts":[[2023,9,27]]}},"URL":"https:\/\/doi.org\/10.1039\/d3ob01208e","relation":{},"ISSN":["1477-0520","1477-0539"],"issn-type":[{"value":"1477-0520","type":"print"},{"value":"1477-0539","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023]]}}}