Optically active α-amino 4H-[1,2,4]oxadiazol-5-ones (oxadiazolones) were prepared from optically active α-amino acids in five synthetic steps. The oxadiazolone moiety serves as a bioisosteric replacement for the carboxylic acid. Incorporation of an α-amino oxadiazolone into a representative dipeptide mimic is described.

A series of oxadiazolone bioisosteres of pregabalin 1 and gabapentin 2 were prepared, and several were found to exhibit similar potency for the alpha(2)-delta subunit of voltage-gated calcium channels. Oxadiazolone 9 derived from 2 achieved low brain uptake but was nevertheless active in models of osteoarthritis. The high clearance associated with compound 9 was postulated to be a consequence of efflux by OAT and/or OCT, and was attenuated on co-administration with cimetidine or probenecid.

Abstractβ‐Cyclohexenyl‐amin (I) liefert mit der Phenylessigsäure (II) über das Amid (III) das Octahydro‐isochinolin (Vb), das bei der Behandlung mit HBr zu (VI) cyclisiert wird.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXT1-(2-Imidazolin-2-yl)-2-imidazolines. I. Structure of Jaffe's base and the chemistry of related compoundsRaymond R. Wittekind, Thomas Capiris, John Fahey, and John Shavel Jr.Cite this: J. Org. Chem. 1973, 38, 9, 1641–1645Publication Date (Print):May 1, 1973Publication History Published online1 May 2002Published inissue 1 May 1973https://doi.org/10.1021/jo00949a004Request reuse permissionsArticle Views121Altmetric-Citations7LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (705 KB) Get e-Alertsclose Get e-Alerts

AbstractBei der Kondensation zwischen 2‐Methylmercapto‐imidazolin (I) und seine Hydrojodid (II) entsteht das Dimere (III) neben dem Triimidazolin (IV) un dem Imidazotriazepin (V).

Journal of Heterocyclic ChemistryVolume 9, Issue 6 p. 1441-1444 Note The demethylation of 1,2,3,4,5,6,7,8-octahydro-1-(2-methoxybenzyl)-2-methylisoquinoline. The synthesis of 1-hydroxy-N-methylmorphinan and 1,2,3,4,4a,5,6,7,7a,8-deeahydro-7-methyl[1]benzopyrano[2,3-j]isoquinoline Raymond R. Wittekind, Raymond R. Wittekind Department of Organic Chemistry, Warner-Lambert Research Institute, Morris Plains, New Jersey 07950Search for more papers by this authorThomas Capiris, Thomas Capiris Department of Organic Chemistry, Warner-Lambert Research Institute, Morris Plains, New Jersey 07950Search for more papers by this authorSam Lazarus, Sam Lazarus Department of Organic Chemistry, Warner-Lambert Research Institute, Morris Plains, New Jersey 07950Search for more papers by this author Raymond R. Wittekind, Raymond R. Wittekind Department of Organic Chemistry, Warner-Lambert Research Institute, Morris Plains, New Jersey 07950Search for more papers by this authorThomas Capiris, Thomas Capiris Department of Organic Chemistry, Warner-Lambert Research Institute, Morris Plains, New Jersey 07950Search for more papers by this authorSam Lazarus, Sam Lazarus Department of Organic Chemistry, Warner-Lambert Research Institute, Morris Plains, New Jersey 07950Search for more papers by this author First published: December 1972 https://doi.org/10.1002/jhet.5570090649Citations: 9AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Citing Literature Volume9, Issue6December 1972Pages 1441-1444 RelatedInformation

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTTetracyclic Phenothiazines and Related Compounds. III. Preparation of Cyclic Hydroxypyridones from Arylamines and Malonic Esters1M. Harfenist, R. Blumfeld, T. Capiris, and E. MagnienCite this: J. Org. Chem. 1962, 27, 11, 3977–3982Publication Date (Print):November 1, 1962Publication History Published online1 May 2002Published inissue 1 November 1962https://pubs.acs.org/doi/10.1021/jo01058a053https://doi.org/10.1021/jo01058a053research-articleACS PublicationsRequest reuse permissionsArticle Views80Altmetric-Citations4LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts