{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/67222"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/67222","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Synthesis of Functional Analogs of Non-Steroidal Estrogens","abstract":"The synthesis and biochemical characteristics of several new, functionalized non-steroidal estrogens is reported. With the aim of developing an estrogen receptor-based radiopharmaceutical, two new iodinated estrogens, 1-(2'-iodo-4'-hydroxyphenyl)-2-(4'-hydroxyphenyl)butane and erythro-3-(2'-iodo-4'-hydroxyphenyl)-4-(4'-hydroxyphenyl)hexane (2'-iodohexestrol), were prepared. The relative binding affinities of these compounds for the estrogen receptor in vitro were 50 and 30, respectively, the highest yet achieved for estrogens bearing aryl iodides. For photoaffinity labeling studies of the estrogen receptor, a new photoreactive ligand, 1-(4'-hydroxyphenyl)-2-(2'-nitro-4'-methoxyphenyl)butane, was prepared by total synthesis (nine steps). This compound exhibited a low relative binding affinity for receptor, but a high (58%) inactivation efficiency (ability to destroy binding capacity) when photolyzed in the binding site.","abstract_html":"The synthesis and biochemical characteristics of several new, functionalized non-steroidal estrogens is reported. With the aim of developing an estrogen receptor-based radiopharmaceutical, two new iodinated estrogens, 1-(2'-iodo-4'-hydroxyphenyl)-2-(4'-hydroxyphenyl)butane and erythro-3-(2'-iodo-4'-hydroxyphenyl)-4-(4'-hydroxyphenyl)hexane (2'-iodohexestrol), were prepared. The relative binding affinities of these compounds for the estrogen receptor in vitro were 50 and 30, respectively, the highest yet achieved for estrogens bearing aryl iodides. For photoaffinity labeling studies of the estrogen receptor, a new photoreactive ligand, 1-(4'-hydroxyphenyl)-2-(2'-nitro-4'-methoxyphenyl)butane, was prepared by total synthesis (nine steps). This compound exhibited a low relative binding affinity for receptor, but a high (58%) inactivation efficiency (ability to destroy binding capacity) when photolyzed in the binding site.","abstract_has_math":false,"creators":["Kilbourn, Michael Robert"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2014,"date_issued":"2014-12-13T20:10:53Z","date_published":"2014-12-13T20:10:53Z","updated_at":"2026-07-22T22:25:57Z","subjects":["Chemistry, Organic"],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["(UMI)AAI8017962"],"render_values":[{"text":"(UMI)AAI8017962","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/67222","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Kilbourn, Michael Robert"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2014-12-13T20:10:53Z","10000-01-01","1980"]},{"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, Organic"]}]},{"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/2142/67222","(UMI)AAI8017962"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["The synthesis and biochemical characteristics of several new, functionalized non-steroidal estrogens is reported. With the aim of developing an estrogen receptor-based radiopharmaceutical, two new iodinated estrogens, 1-(2'-iodo-4'-hydroxyphenyl)-2-(4'-hydroxyphenyl)butane and erythro-3-(2'-iodo-4'-hydroxyphenyl)-4-(4'-hydroxyphenyl)hexane (2'-iodohexestrol), were prepared. The relative binding affinities of these compounds for the estrogen receptor in vitro were 50 and 30, respectively, the highest yet achieved for estrogens bearing aryl iodides. For photoaffinity labeling studies of the estrogen receptor, a new photoreactive ligand, 1-(4'-hydroxyphenyl)-2-(2'-nitro-4'-methoxyphenyl)butane, was prepared by total synthesis (nine steps). This compound exhibited a low relative binding affinity for receptor, but a high (58%) inactivation efficiency (ability to destroy binding capacity) when photolyzed in the binding site.","The binding affinities of conformationally flexible ligands, such as the hexestrols and isobutestrol (1,2-bis(4'-hydroxyphenyl)butane), has been attributed to differing equilibrium populations of the antiperiplanar conformer; the conformer populations were determined by Force Field calculations of steric energy for rotations of model compounds. The data suggest that the receptor binds only the antiperiplanar, and not the synclinical, conformer of a flexible ligand.","Made available in DSpace on 2014-12-13T20:10:53Z (GMT). No. of bitstreams: 1 8017962.pdf: 6954908 bytes, checksum: 8f63d6d52a1dadd522276316d20f61b1 (MD5) Previous issue date: 1980","Embargo set by: Seth Robbins for item 67400 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","U of I Only","272 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1980."]},{"key":"dc:title","label":"Title","values":["Synthesis of Functional Analogs of Non-Steroidal Estrogens"]}]}],"canonical_facts":{"dc:creator":["Kilbourn, Michael Robert"],"dc:date":["2014-12-13T20:10:53Z","10000-01-01","1980"],"dc:description":["The synthesis and biochemical characteristics of several new, functionalized non-steroidal estrogens is reported. With the aim of developing an estrogen receptor-based radiopharmaceutical, two new iodinated estrogens, 1-(2'-iodo-4'-hydroxyphenyl)-2-(4'-hydroxyphenyl)butane and erythro-3-(2'-iodo-4'-hydroxyphenyl)-4-(4'-hydroxyphenyl)hexane (2'-iodohexestrol), were prepared. The relative binding affinities of these compounds for the estrogen receptor in vitro were 50 and 30, respectively, the highest yet achieved for estrogens bearing aryl iodides. For photoaffinity labeling studies of the estrogen receptor, a new photoreactive ligand, 1-(4'-hydroxyphenyl)-2-(2'-nitro-4'-methoxyphenyl)butane, was prepared by total synthesis (nine steps). This compound exhibited a low relative binding affinity for receptor, but a high (58%) inactivation efficiency (ability to destroy binding capacity) when photolyzed in the binding site.","The binding affinities of conformationally flexible ligands, such as the hexestrols and isobutestrol (1,2-bis(4'-hydroxyphenyl)butane), has been attributed to differing equilibrium populations of the antiperiplanar conformer; the conformer populations were determined by Force Field calculations of steric energy for rotations of model compounds. The data suggest that the receptor binds only the antiperiplanar, and not the synclinical, conformer of a flexible ligand.","Made available in DSpace on 2014-12-13T20:10:53Z (GMT). No. of bitstreams: 1 8017962.pdf: 6954908 bytes, checksum: 8f63d6d52a1dadd522276316d20f61b1 (MD5) Previous issue date: 1980","Embargo set by: Seth Robbins for item 67400 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","U of I Only","272 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1980."],"dc:identifier":["http://hdl.handle.net/2142/67222","(UMI)AAI8017962"],"dc:language":["eng"],"dc:subject":["Chemistry, Organic"],"dc:title":["Synthesis of Functional Analogs of Non-Steroidal Estrogens"],"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":"2026-07-22T22:25:57Z"}