{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,16]],"date-time":"2026-06-16T21:49:51Z","timestamp":1781646591166,"version":"3.54.5"},"reference-count":0,"publisher":"International Union of Crystallography (IUCr)","issue":"4","license":[{"start":{"date-parts":[[2004,7,19]],"date-time":"2004-07-19T00:00:00Z","timestamp":1090195200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2004,7,19]],"date-time":"2004-07-19T00:00:00Z","timestamp":1090195200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html#TDM"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr B Struct Sci","Acta Cryst B","Acta Cryst Sect B","Acta Crystallogr B","Acta Crystallogr Sect B","Acta Crystallogr Sect B Struct Sci"],"accepted":{"date-parts":[[2004,6,4]]},"published-print":{"date-parts":[[2004,8,1]]},"abstract":"<jats:p>\u03b2-Carbolines are a class of drug which can interact with a high affinity with the benzodiazepine (BDZ) binding site of the GABA<jats:sub>A<\/jats:sub> receptor. The present paper, aimed at obtaining a deeper insight into the structure\u2013properties relationships of this class of molecules, reports the crystal structures of four \u03b2-carbolines: ZK93423 (3-carboethoxy-4-methoxymethyl-6-benzyloxy-\u03b2-carboline), ZK91296 (3-carboethoxy-4-methoxymethyl-5-benzyloxy-\u03b2-carboline), FG7142 (<jats:italic>N<\/jats:italic>-methyl-3-carbamoyl-\u03b2-carboline) and the low-affinity ligand harmine hydrochloride (1-methyl-7-methoxy-\u03b2-carboline). This set of structural data is completed by the X-ray structures of other carbolines of known biological activity retrieved from the Cambridge Crystallographic Database and by the structures of \u03b2-CCE (3-carboethoxy-\u03b2-carboline), 6-PBC (3-carboethoxy-4-methoxymethyl-6-isopropoxy-\u03b2-carboline), PRCC (3-isopropoxy-\u03b2-carboline) and ZK93426 (3-carboethoxy-4-methyl-5-isopropoxy-\u03b2-carboline), which have been obtained by molecular-mechanics simulations. The structural features of all these molecules have been compared according to the stereochemical model we proposed in 1987. The structural comparison is integrated by the Free\u2013Wilson analysis on 32 \u03b2-carbolines of known binding affinity data.<\/jats:p>","DOI":"10.1107\/s0108768104013564","type":"journal-article","created":{"date-parts":[[2004,7,19]],"date-time":"2004-07-19T11:25:45Z","timestamp":1090236345000},"page":"481-489","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":15,"title":["Structural features controlling the binding of \u03b2-carbolines to the benzodiazepine receptor"],"prefix":"10.1107","volume":"60","author":[{"given":"Valeria","family":"Ferretti","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paola","family":"Gilli","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pier Andrea","family":"Borea","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2004,7,19]]},"container-title":["Acta Crystallographica Section B Structural Science"],"original-title":[],"link":[{"URL":"http:\/\/journals.iucr.org\/b\/issues\/2004\/04\/00\/na5019\/na5019.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/journals.iucr.org\/b\/issues\/2004\/04\/00\/na5019\/na5019.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,11]],"date-time":"2025-01-11T12:40:05Z","timestamp":1736599205000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S0108768104013564"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2004,7,19]]},"references-count":0,"journal-issue":{"issue":"4","published-print":{"date-parts":[[2004,8]]}},"alternative-id":["S0108768104013564"],"URL":"https:\/\/doi.org\/10.1107\/s0108768104013564","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S0108768104013564\/na5019sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S0108768104013564\/na5019ZK93423sup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S0108768104013564\/na5019ZK91296sup3.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S0108768104013564\/na5019FG7142sup4.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S0108768104013564\/na5019Harminesup5.hkl","asserted-by":"subject"}]},"ISSN":["0108-7681"],"issn-type":[{"value":"0108-7681","type":"print"}],"subject":[],"published":{"date-parts":[[2004,7,19]]},"assertion":[{"value":"Acta Crystallographica Section B: Structural Science","order":0,"name":"journal","label":"Publication","explanation":{"URL":"http:\/\/journals.iucr.org\/b"},"group":{"name":"general","label":"General"}},{"value":"research papers","order":1,"name":"content_type","label":"Content type","explanation":{"URL":"https:\/\/journals.iucr.org\/b\/services\/notesforauthors.html"},"group":{"name":"general","label":"General"}},{"value":"Available","URL":"http:\/\/scripts.iucr.org\/cgi-bin\/citedin?na5019","order":2,"name":"article_metrics","label":"Article metrics","group":{"name":"general","label":"General"}},{"value":"Yes","order":0,"name":"peer_reviewed","label":"Peer reviewed","group":{"name":"peer_review","label":"Peer review"}},{"value":"Single blind","order":1,"name":"review_process","label":"Review process","group":{"name":"peer_review","label":"Peer review"}},{"value":"20 May 2004","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"4 June 2004","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"19 July 2004","order":2,"name":"published_online","label":"Published online","group":{"name":"publication_history","label":"Publication history"}},{"value":"This article has supporting information","name":"supplementary_materials","label":"Supplementary materials","explanation":{"URL":"http:\/\/scripts.iucr.org\/cgi-bin\/sendsup?na5019"}},{"value":"\u00a9 2004 International Union of Crystallography","order":0,"name":"copyright","label":"Copyright","explanation":{"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},"group":{"name":"copyright_and_licensing","label":"Copyright and licencing"}}]}}