{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/84488"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/84488","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Development of Novel Subtype Selective Ligands for the Estrogen Receptor: I. 5,6-Diakyl-5,6,11,12-Tetrahydrochrysenes as Estrogen Receptor-Beta Selective Antagonists. II. Diarylpropionitriles as Estrogen Receptor-Beta Potency Selective Agonists","abstract":"A series of ERbeta selective DPN analogs were prepared where the both the ligand core and the aromatic rings were modified by the repositioning of phenolic hydroxy groups and by the addition of alkyl substituents and nitrile groups. Another series of DPN analogs were synthesized where the nitrile functionality was replaced with acetylene groups or polar groups to mimic the linear geometry or the polarity of the nitrile. All of the analogs are affinity selective for ERbeta to varying degrees, but many are not potency selective. meso- and dl-2,3-bis(4-hydroxyphenyl)succinonitrile are among the highest ERbeta affinity selective ligands and have somewhat greater ERbeta potency selectivity than DPN. The nitrile functionality was found to be critical to ERbeta selectivity as it is the optimal combination of linear geometry and polarity. Furthermore, the addition of another nitrile group beta to the nitrile or ortho methylation of the aromatic ring increases the affinity and selectivity of these compounds for ERbeta.","abstract_html":"A series of ERbeta selective DPN analogs were prepared where the both the ligand core and the aromatic rings were modified by the repositioning of phenolic hydroxy groups and by the addition of alkyl substituents and nitrile groups. Another series of DPN analogs were synthesized where the nitrile functionality was replaced with acetylene groups or polar groups to mimic the linear geometry or the polarity of the nitrile. All of the analogs are affinity selective for ERbeta to varying degrees, but many are not potency selective. meso- and dl-2,3-bis(4-hydroxyphenyl)succinonitrile are among the highest ERbeta affinity selective ligands and have somewhat greater ERbeta potency selectivity than DPN. The nitrile functionality was found to be critical to ERbeta selectivity as it is the optimal combination of linear geometry and polarity. Furthermore, the addition of another nitrile group beta to the nitrile or ortho methylation of the aromatic ring increases the affinity and selectivity of these compounds for ERbeta.","abstract_has_math":false,"creators":["Meyers, Marvin Jay"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Katzenellenbogen, John A."],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2015,"date_issued":"2015-09-25T22:14:46Z","date_published":"2015-09-25T22:14:46Z","updated_at":"2026-07-22T22:26:23Z","subjects":["Chemistry, Biochemistry"],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["(MiAaPQ)AAI9990083"],"render_values":[{"text":"(MiAaPQ)AAI9990083","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/84488","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Katzenellenbogen, John A."]},{"key":"dc:creator","label":"Author","values":["Meyers, Marvin Jay"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2015-09-25T22:14:46Z","10000-01-01","2000"]},{"key":"dc:type","label":"Dc Type","values":["text"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Ph.D."]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Illinois at Urbana-Champaign"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry, Biochemistry"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["eng"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/2142/84488","(MiAaPQ)AAI9990083"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["A series of ERbeta selective DPN analogs were prepared where the both the ligand core and the aromatic rings were modified by the repositioning of phenolic hydroxy groups and by the addition of alkyl substituents and nitrile groups. Another series of DPN analogs were synthesized where the nitrile functionality was replaced with acetylene groups or polar groups to mimic the linear geometry or the polarity of the nitrile. All of the analogs are affinity selective for ERbeta to varying degrees, but many are not potency selective. meso- and dl-2,3-bis(4-hydroxyphenyl)succinonitrile are among the highest ERbeta affinity selective ligands and have somewhat greater ERbeta potency selectivity than DPN. The nitrile functionality was found to be critical to ERbeta selectivity as it is the optimal combination of linear geometry and polarity. Furthermore, the addition of another nitrile group beta to the nitrile or ortho methylation of the aromatic ring increases the affinity and selectivity of these compounds for ERbeta.","Made available in DSpace on 2015-09-25T22:14:46Z (GMT). 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Diarylpropionitriles as Estrogen Receptor-Beta Potency Selective Agonists"]}]}],"canonical_facts":{"dc:contributor":["Katzenellenbogen, John A."],"dc:creator":["Meyers, Marvin Jay"],"dc:date":["2015-09-25T22:14:46Z","10000-01-01","2000"],"dc:description":["A series of ERbeta selective DPN analogs were prepared where the both the ligand core and the aromatic rings were modified by the repositioning of phenolic hydroxy groups and by the addition of alkyl substituents and nitrile groups. Another series of DPN analogs were synthesized where the nitrile functionality was replaced with acetylene groups or polar groups to mimic the linear geometry or the polarity of the nitrile. All of the analogs are affinity selective for ERbeta to varying degrees, but many are not potency selective. meso- and dl-2,3-bis(4-hydroxyphenyl)succinonitrile are among the highest ERbeta affinity selective ligands and have somewhat greater ERbeta potency selectivity than DPN. The nitrile functionality was found to be critical to ERbeta selectivity as it is the optimal combination of linear geometry and polarity. Furthermore, the addition of another nitrile group beta to the nitrile or ortho methylation of the aromatic ring increases the affinity and selectivity of these compounds for ERbeta.","Made available in DSpace on 2015-09-25T22:14:46Z (GMT). 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Diarylpropionitriles as Estrogen Receptor-Beta Potency Selective Agonists"],"dc:type":["text"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Dissertation"],"thesis:degree_name":["Ph.D."],"thesis:institution_name":["University of Illinois at Urbana-Champaign"]},"updated_at":"2026-07-22T22:26:23Z"}