{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,11]],"date-time":"2026-05-11T17:15:32Z","timestamp":1778519732393,"version":"3.51.4"},"reference-count":47,"publisher":"Elsevier BV","issue":"4","license":[{"start":{"date-parts":[[1999,4,1]],"date-time":"1999-04-01T00:00:00Z","timestamp":922924800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[1999,4,1]],"date-time":"1999-04-01T00:00:00Z","timestamp":922924800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2013,7,17]],"date-time":"2013-07-17T00:00:00Z","timestamp":1374019200000},"content-version":"vor","delay-in-days":5221,"URL":"http:\/\/www.elsevier.com\/open-access\/userlicense\/1.0\/"}],"funder":[{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["GM 27029"],"award-info":[{"award-number":["GM 27029"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["CHE 96-10502"],"award-info":[{"award-number":["CHE 96-10502"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000888","name":"W. M. Keck Foundation","doi-asserted-by":"publisher","award":["PHS 1 SlO RR104444-01"],"award-info":[{"award-number":["PHS 1 SlO RR104444-01"]}],"id":[{"id":"10.13039\/100000888","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["RR 01575"],"award-info":[{"award-number":["RR 01575"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["PCM 8121494"],"award-info":[{"award-number":["PCM 8121494"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["PHS 5R37 DKI 5556"],"award-info":[{"award-number":["PHS 5R37 DKI 5556"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["cell.com","elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Chemistry & Biology"],"published-print":{"date-parts":[[1999,4]]},"DOI":"10.1016\/s1074-5521(99)80037-4","type":"journal-article","created":{"date-parts":[[2002,7,25]],"date-time":"2002-07-25T21:56:33Z","timestamp":1027634193000},"page":"205-219","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":200,"title":["Novel structural templates for estrogen-receptor ligands and prospects for combinatorial synthesis of estrogens"],"prefix":"10.1016","volume":"6","author":[{"given":"Brian E","family":"Fink","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Deborah S","family":"Mortensen","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shaun R","family":"Stauffer","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Zachary D","family":"Aron","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"John A","family":"Katzenellenbogen","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"78","reference":[{"key":"10.1016\/S1074-5521(99)80037-4_bib1","first-page":"14105","article-title":"Molecular determinants of tissue selectivity in estrogen receptor modulators","volume":"94","author":"Grese","year":"1997"},{"key":"10.1016\/S1074-5521(99)80037-4_bib2","first-page":"5925","article-title":"Cloning of a novel receptor expressed in rat prostate and ovary","volume":"93","author":"Kuiper","year":"1996"},{"key":"10.1016\/S1074-5521(99)80037-4_bib3","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1016\/0014-5793(96)00782-X","article-title":"ERb: Identification and charaterization of a novel human estrogen receptor","volume":"392","author":"Mosselman","year":"1996","journal-title":"FEBS Lett."},{"key":"10.1016\/S1074-5521(99)80037-4_bib4","doi-asserted-by":"crossref","first-page":"529","DOI":"10.1016\/S1074-5521(96)90143-X","article-title":"Nuclear hormone receptors: ligand-activated regulators of transcription and diverse cell responses","volume":"3","author":"Katzenellenbogen","year":"1996","journal-title":"Chem. Biol."},{"key":"10.1016\/S1074-5521(99)80037-4_bib5","first-page":"1167","article-title":"Nuclear receptor coactivators and corepressors","volume":"10","author":"Horwitz","year":"1996","journal-title":"Mol. Endocrinol."},{"key":"10.1016\/S1074-5521(99)80037-4_bib6","doi-asserted-by":"crossref","first-page":"222","DOI":"10.1016\/S0955-0674(97)80066-X","article-title":"Nuclear receptor coactivators","volume":"9","author":"Glass","year":"1997","journal-title":"Curr. Opin. Cell. Biol."},{"key":"10.1016\/S1074-5521(99)80037-4_bib7","first-page":"119","article-title":"Tripartite steroid hormone receptor pharmacology: interaction with multiple effector sites as a basis for the cell-and promoter-specific action of these hormones","volume":"10","author":"Katzenellenbogen","year":"1996","journal-title":"Mol. Endocrinol."},{"key":"10.1016\/S1074-5521(99)80037-4_bib8","doi-asserted-by":"crossref","first-page":"61","DOI":"10.2174\/0929867301666220210212635","article-title":"The medicinal chemistry of nonsteroidal antiestrogens: a review","volume":"1","author":"Magarian","year":"1994","journal-title":"Curr. Med. Chem."},{"key":"10.1016\/S1074-5521(99)80037-4_bib9","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1021\/cr50014a002","article-title":"Artificial estrogens","volume":"57","author":"Grundy","year":"1957","journal-title":"Chem. Rev."},{"key":"10.1016\/S1074-5521(99)80037-4_bib10","doi-asserted-by":"crossref","first-page":"481","DOI":"10.1021\/cr60118a004","article-title":"Synthetic estrogens and the relation between their structure and their activity","volume":"37","author":"Solmssen","year":"1945","journal-title":"Chem. Rev."},{"key":"10.1016\/S1074-5521(99)80037-4_bib11","doi-asserted-by":"crossref","first-page":"1272","DOI":"10.1021\/jm970688z","article-title":"Synthesis and pharmacology of conformationally restricted raloxifene analogues: highly potent selective estrogen receptor modulators","volume":"41","author":"Grese","year":"1998","journal-title":"J. Med. Chem."},{"key":"10.1016\/S1074-5521(99)80037-4_bib12","doi-asserted-by":"crossref","first-page":"1407","DOI":"10.1021\/jm970167b","article-title":"Discovery and synthesis of [6-Hydroxy-3-[4-[2-(1-piperidinyl)ethoxy]phenoxy]-2- (hydroxyphenyl)]benzo[b]hiophene: a novel, highly potent, selective estrogen receptor modulator","volume":"40","author":"Plakowitz","year":"1997","journal-title":"J. Med. Chem."},{"key":"10.1016\/S1074-5521(99)80037-4_bib13","doi-asserted-by":"crossref","first-page":"6331","DOI":"10.1021\/ja961203j","article-title":"Synthesis of tetra-substituted ethylenes on solid support via resin capture","volume":"118","author":"Brown","year":"1996","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/S1074-5521(99)80037-4_bib14","first-page":"45","article-title":"Screening and characterization of estrogenic activity from hydroxystilbene library","volume":"2","author":"Williard","year":"1995","journal-title":"Curr. Biol."},{"key":"10.1016\/S1074-5521(99)80037-4_bib15","doi-asserted-by":"crossref","first-page":"835","DOI":"10.1016\/0040-4039(95)02334-8","article-title":"Imidazole libraries on solid support","volume":"37","author":"Sarshar","year":"1996","journal-title":"Tetrahedron Lett"},{"key":"10.1016\/S1074-5521(99)80037-4_bib16","doi-asserted-by":"crossref","first-page":"338","DOI":"10.1002\/cber.19590920214","article-title":"Imidazole aus \u03b1-diketonen","volume":"92","author":"Bredereck","year":"1959","journal-title":"Chem. Ber."},{"key":"10.1016\/S1074-5521(99)80037-4_bib17","doi-asserted-by":"crossref","first-page":"1182","DOI":"10.1021\/jm00257a011","article-title":"Preparation and antiinflammatory activity of some nonacidic trisubstituted imidazoles","volume":"17","author":"Lombardino","year":"1974","journal-title":"J. Med. Chem."},{"key":"10.1016\/S1074-5521(99)80037-4_bib18","doi-asserted-by":"crossref","first-page":"192","DOI":"10.1002\/prac.19620180312","article-title":"p-Aryl- und p-Alkoxyphenyl-imidazole","volume":"18","author":"Schubert","year":"1962","journal-title":"J. Prakt. Chem."},{"key":"10.1016\/S1074-5521(99)80037-4_bib19","doi-asserted-by":"crossref","first-page":"575","DOI":"10.3987\/COM-93-6595","article-title":"A novel synthesis of 2,4,5-triarylimidazoles","volume":"38","author":"Hayes","year":"1994","journal-title":"Heterocycles"},{"key":"10.1016\/S1074-5521(99)80037-4_bib20","doi-asserted-by":"crossref","first-page":"3421","DOI":"10.1021\/ja01595a043","article-title":"Organic peracid oxidation of some enol esters involving re-arrangement","volume":"78","author":"Gardner","year":"1956","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/S1074-5521(99)80037-4_bib21","doi-asserted-by":"crossref","first-page":"682","DOI":"10.1021\/ja01318a043","article-title":"The grignard reaction in the synthesis of ketones. IV. A new method of preparing isomeric unsymmetrical benzoins","volume":"56","author":"Jenkins","year":"1934","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/S1074-5521(99)80037-4_bib22","doi-asserted-by":"crossref","first-page":"2368","DOI":"10.1021\/jo00113a015","article-title":"Base-promoted reactions of \u03b1-azido ketones with aldehydes and ketones: a novel entry to \u03b1- azido-hydroxy ketones and 2,5-dihydro-5-hydroxyoxazoles","volume":"60","author":"Patonay","year":"1995","journal-title":"J. Org. Chem."},{"key":"10.1016\/S1074-5521(99)80037-4_bib23","doi-asserted-by":"crossref","first-page":"2656","DOI":"10.1021\/ja01495a078","article-title":"A new synthesis of aliphatic and aromatic thioamides from nitriles","volume":"82","author":"Taylor","year":"1960","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/S1074-5521(99)80037-4_bib24","doi-asserted-by":"crossref","first-page":"643","DOI":"10.1002\/prac.19793210417","article-title":"Kristallin-flussige Thiazole. [Liquid-crystalline thiazoles.]","volume":"321","author":"Dolling","year":"1979","journal-title":"J. Prakt. Chem."},{"key":"10.1016\/S1074-5521(99)80037-4_bib25","doi-asserted-by":"crossref","first-page":"1519","DOI":"10.1039\/JR9600001519","article-title":"Interaction at a distance in conjugated systems. Part III. Effect of aryl and heteroaryl groups on the infrared intensities of C=C and C C stretching bands","author":"Katrizky","year":"1960","journal-title":"J. Chem. Soc."},{"key":"10.1016\/S1074-5521(99)80037-4_bib26","doi-asserted-by":"crossref","first-page":"347","DOI":"10.1039\/jr9400000347","article-title":"Mechanism of the reaction between arylamines and benzoins","author":"Cowper","year":"1940","journal-title":"J. Chem. Soc."},{"key":"10.1016\/S1074-5521(99)80037-4_bib27","first-page":"158","article-title":"Reaction of \u03b1-acyloxyketones with ammonium acetate","volume":"22","author":"Strzybny","year":"1969","journal-title":"J. South African Chem. Inst."},{"key":"10.1016\/S1074-5521(99)80037-4_bib28","doi-asserted-by":"crossref","first-page":"1003","DOI":"10.1016\/0040-4039(95)02370-4","article-title":"Solid support synthesis of highly functionalized pyrazoles and isoxazoles; scaffolds for molecular diversity","volume":"37","author":"Marzinzik","year":"1996","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/S1074-5521(99)80037-4_bib29","doi-asserted-by":"crossref","first-page":"5428","DOI":"10.1021\/ja00485a030","article-title":"Dipolestabilized carbanions from thioesters Evidence for stabilization by the carbonyl group","volume":"100","author":"Reitz","year":"1978","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/S1074-5521(99)80037-4_bib30","first-page":"62","article-title":"Studies in antifertility agents: Part XXII: 1,2-diethyl-1,3-bis-(p-hydroxyphenyl)-1-propene","volume":"18B","author":"Tewari","year":"1979","journal-title":"Ind. J. Chem."},{"key":"10.1016\/S1074-5521(99)80037-4_bib31","doi-asserted-by":"crossref","first-page":"1743","DOI":"10.1039\/P19770001743","article-title":"Hydrogen bonding in organic synthesis. Part 6. C-Alkylation of \u03b2-dicarbonyl compounds using tetralkylammonium fluorides","author":"Clark","year":"1977","journal-title":"J. Chem. Soc., Perkinl"},{"key":"10.1016\/S1074-5521(99)80037-4_bib32","first-page":"278","article-title":"3-(4-Chlorophenyl)-5-(4-methoxyphenyl)isoxazole","volume":"Vol. VI","author":"Perkins","year":"1988","journal-title":"Org. Syn. Coll."},{"key":"10.1016\/S1074-5521(99)80037-4_bib33","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1246\/cl.1988.233","article-title":"A novel NO insertion into cyclopropane ring by use of NOBF4. Formation of 2-isoxazolines","author":"Ichinose","year":"1988","journal-title":"Chem. Lett."},{"key":"10.1016\/S1074-5521(99)80037-4_bib34","doi-asserted-by":"crossref","first-page":"2315","DOI":"10.1071\/CH9682315","article-title":"Isoxazolylphenols and their absorption spectra","volume":"21","author":"Murthy","year":"1968","journal-title":"Aus. J. Chem."},{"key":"10.1016\/S1074-5521(99)80037-4_bib35","doi-asserted-by":"crossref","first-page":"1964","DOI":"10.1021\/bi00628a033","article-title":"Estrogen photoaffinity labels. 1. Chemical and radiochemical synthesis of hexestrol diazoketone and azide derivatives; photochemical studies in solution","volume":"16","author":"Katzenellenbogen","year":"1977","journal-title":"Biochemistry"},{"key":"10.1016\/S1074-5521(99)80037-4_bib36","doi-asserted-by":"crossref","first-page":"268","DOI":"10.1016\/S0039-128X(96)00242-5","article-title":"The estradiol pharmacophore: ligand structure-estrogen receptor binding affinity relationships and a model for the receptor binding site","volume":"62","author":"Anstead","year":"1997","journal-title":"Steroids"},{"key":"10.1016\/S1074-5521(99)80037-4_bib37","doi-asserted-by":"crossref","first-page":"1439","DOI":"10.1021\/jm00377a011","article-title":"2-Phenylindoles. Relationship between structure, estrogen receptor affinity, and mammary tumor inhibiting activity in the rat","volume":"27","author":"von Angerer","year":"1984","journal-title":"J. Med. Chem."},{"key":"10.1016\/S1074-5521(99)80037-4_bib38","doi-asserted-by":"crossref","first-page":"1262","DOI":"10.1021\/jo00030a039","article-title":"5,6,11,12-Tetrahydrochrysenes: Synthesis of rigid stilbene systems designed to be fluorescent ligands for the estrogen receptor","volume":"57","author":"Hwang","year":"1992","journal-title":"J. Org. Chem."},{"key":"10.1016\/S1074-5521(99)80037-4_bib39","first-page":"516","author":"Joule","year":"1995"},{"key":"10.1016\/S1074-5521(99)80037-4_bib40","doi-asserted-by":"crossref","first-page":"557","DOI":"10.1016\/0960-0760(92)90383-T","article-title":"3-Alkyl-2-phenylbenzo[b]thiophenes: nonsteroidal estrogen antagonists with mammary tumor inhibiting activity","volume":"41","author":"von Angerer","year":"1992","journal-title":"J. Steroid Biochem. Mol. Biol."},{"key":"10.1016\/S1074-5521(99)80037-4_bib41","doi-asserted-by":"crossref","first-page":"903","DOI":"10.1016\/0960-894X(96)00141-2","article-title":"Benzopyran selective estrogen receptor modulators (SERMS): Pharmacological effects and structural correlation with raloxifene","volume":"6","author":"Grese","year":"1996","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/S1074-5521(99)80037-4_bib42","doi-asserted-by":"crossref","first-page":"753","DOI":"10.1038\/39645","article-title":"Molecular basis of agonism and antagonism in the oestrogen receptor","volume":"389","author":"Brzozowski","year":"1997","journal-title":"Nature"},{"key":"10.1016\/S1074-5521(99)80037-4_bib43","doi-asserted-by":"crossref","first-page":"800","DOI":"10.1210\/endo.140.2.6480","article-title":"Novel ligands that function as selective estrogens or antiestrogens for estrogen receptor-\u03b1 or estrogen receptor-\u03b2","volume":"140","author":"Sun","year":"1999","journal-title":"Endocrinology"},{"key":"10.1016\/S1074-5521(99)80037-4_bib44","doi-asserted-by":"crossref","first-page":"4085","DOI":"10.1021\/bi00745a010","article-title":"Photoaffinity labels for estrogen binding proteins of rat uterus","volume":"12","author":"Katzenellenbogen","year":"1973","journal-title":"Biochemistry"},{"key":"10.1016\/S1074-5521(99)80037-4_bib45","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1002\/recl.19470660104","article-title":"The nitration of dianisoylmethane and p-methoxydesoxybenzoin","volume":"66","author":"van Steenis","year":"1946","journal-title":"Recl. Trav. Chim. Pays-Bas"},{"key":"10.1016\/S1074-5521(99)80037-4_bib46","doi-asserted-by":"crossref","first-page":"542","DOI":"10.1021\/jo00152a025","article-title":"Quenching of singlet oxygen by 1,3,5-triaryl-2-pyraazolines","volume":"48","author":"Ando","year":"1983","journal-title":"J. Org. Chem."},{"key":"10.1016\/S1074-5521(99)80037-4_bib47","doi-asserted-by":"crossref","first-page":"481","DOI":"10.1002\/recl.19911101202","article-title":"New developments in thermally stable polymers","volume":"110","author":"Hergenrother","year":"1991","journal-title":"Rec. Travl. Chim. Pays-Bas"}],"container-title":["Chemistry & Biology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S1074552199800374?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S1074552199800374?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2026,5,11]],"date-time":"2026-05-11T17:04:42Z","timestamp":1778519082000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S1074552199800374"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[1999,4]]},"references-count":47,"journal-issue":{"issue":"4","published-print":{"date-parts":[[1999,4]]}},"alternative-id":["S1074552199800374"],"URL":"https:\/\/doi.org\/10.1016\/s1074-5521(99)80037-4","relation":{},"ISSN":["1074-5521"],"issn-type":[{"value":"1074-5521","type":"print"}],"subject":[],"published":{"date-parts":[[1999,4]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Novel structural templates for estrogen-receptor ligands and prospects for combinatorial synthesis of estrogens","name":"articletitle","label":"Article Title"},{"value":"Chemistry & Biology","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/S1074-5521(99)80037-4","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"Copyright \u00a9 1999 Published by Elsevier Ltd.","name":"copyright","label":"Copyright"}]}}