{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,30]],"date-time":"2026-04-30T08:53:55Z","timestamp":1777539235873,"version":"3.51.4"},"reference-count":12,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2010,3,10]],"date-time":"2010-03-10T00:00:00Z","timestamp":1268179200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Archiv der Pharmazie"],"published-print":{"date-parts":[[2010,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The affinities of tetrahydroprotoberberines for dopamine receptors dramatically decrease after cleaving the central C\u2010N bond to the analogous ten\u2010membered dibenzo[<jats:italic>c<\/jats:italic>,<jats:italic>g<\/jats:italic>]azecines [1]. In the present work, we also synthesized eleven\u2010membered homologues of these heterocycles and measured the affinities of the resulting dibenzazaundecenes and their underlying homoberberines for human dopamine receptors as well as the cytotoxic effects of all target compounds on human glia cells. The tetracyclic iso\u2010C\u2010homoberberine\u2010derivatives revealed to be D<jats:sub>4<\/jats:sub>\u2010selective antagonists, while all other active compounds showed a significant D<jats:sub>1<\/jats:sub>\/D<jats:sub>5<\/jats:sub> selectivity. Distances in energy\u2010minimized conformations were measured in order to explain our findings.<\/jats:p>","DOI":"10.1002\/ardp.200900267","type":"journal-article","created":{"date-parts":[[2010,3,10]],"date-time":"2010-03-10T12:57:16Z","timestamp":1268225836000},"page":"207-214","source":"Crossref","is-referenced-by-count":4,"title":["Ring Expansions of Tetrahydroprotoberberines and Related Dibenzo[<i>c,g<\/i>]azecines Modulate the Dopamine Receptor Subtype Affinity and Selectivity"],"prefix":"10.1002","volume":"343","author":[{"given":"Maria","family":"Schulze","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Oliver","family":"Siol","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Werner","family":"Meise","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jochen","family":"Lehmann","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christoph","family":"Enzensperger","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2010,3,24]]},"reference":[{"key":"e_1_2_1_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2009.08.028"},{"key":"e_1_2_1_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm0002432"},{"key":"e_1_2_1_4_2","doi-asserted-by":"crossref","unstructured":"M.Clemens W.Meise K.Himmel M.Jansen Liebigs Ann. 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