{"id":"https://openalex.org/W7214214745","doi":"https://doi.org/10.1248/cpb.c26-00391","title":"Synthesis, Tautomeric Behavior, and Biological Activity of 6-Unsubstituted 2-Aryl-1,4-dihydropyrimidines and 4-Unsubstituted 2-Aryl-1,6-dihydropyrimidines","display_name":"Synthesis, Tautomeric Behavior, and Biological Activity of 6-Unsubstituted 2-Aryl-1,4-dihydropyrimidines and 4-Unsubstituted 2-Aryl-1,6-dihydropyrimidines","publication_year":2026,"publication_date":"2026-09-24","ids":{"openalex":"https://openalex.org/W7214214745","doi":"https://doi.org/10.1248/cpb.c26-00391","pmid":"https://pubmed.ncbi.nlm.nih.gov/42802044"},"language":"en","primary_location":{"id":"doi:10.1248/cpb.c26-00391","doi":"https://doi.org/10.1248/cpb.c26-00391","is_oa":true,"landing_page_url":"https://doi.org/10.1248/cpb.c26-00391","pdf_url":"https://www.jstage.jst.go.jp/article/cpb/74/9/74_c26-00391/_pdf","source":{"id":"https://openalex.org/S3861430","display_name":"Chemical and Pharmaceutical Bulletin","issn_l":"0009-2363","issn":["0009-2363","1347-5223"],"is_oa":true,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-c","jufo-1","medline","norway-1","poland-40","russia-white-list-2"],"host_organization":"https://openalex.org/P4310313382","host_organization_name":"Pharmaceutical Society of Japan","host_organization_lineage":["https://openalex.org/P4310313382"],"host_organization_lineage_names":["Pharmaceutical Society of Japan"],"type":"journal"},"license":"cc-by-nc","license_id":"https://openalex.org/licenses/cc-by-nc","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chemical and Pharmaceutical Bulletin","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref","pubmed"],"open_access":{"is_oa":true,"oa_status":"diamond","oa_url":"https://www.jstage.jst.go.jp/article/cpb/74/9/74_c26-00391/_pdf","any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":null,"display_name":"Yoshio Nishimura","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I30181195","display_name":"Ohu University","ror":"https://ror.org/01fe6f215","country_code":"JP","type":"education","lineage":["https://openalex.org/I30181195"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Yoshio Nishimura","raw_affiliation_strings":["School of Pharmaceutical Sciences, Ohu University, 31\u20131 Misumido, Tomita-machi, Koriyama, Fukushima 963\u20138041, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"School of Pharmaceutical Sciences, Ohu University, 31\u20131 Misumido, Tomita-machi, Koriyama, Fukushima 963\u20138041, Japan","institution_ids":["https://openalex.org/I30181195"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5113234736","display_name":"Keito Taira","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I30181195","display_name":"Ohu University","ror":"https://ror.org/01fe6f215","country_code":"JP","type":"education","lineage":["https://openalex.org/I30181195"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Keito Taira","raw_affiliation_strings":["School of Pharmaceutical Sciences, Ohu University, 31\u20131 Misumido, Tomita-machi, Koriyama, Fukushima 963\u20138041, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"School of Pharmaceutical Sciences, Ohu University, 31\u20131 Misumido, Tomita-machi, Koriyama, Fukushima 963\u20138041, Japan","institution_ids":["https://openalex.org/I30181195"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5048321182","display_name":"Yusuke Yamamoto","orcid":"https://orcid.org/0000-0002-2014-9457","observed_orcids":["https://orcid.org/0000-0002-2014-9457"]},"institutions":[{"id":"https://openalex.org/I30181195","display_name":"Ohu University","ror":"https://ror.org/01fe6f215","country_code":"JP","type":"education","lineage":["https://openalex.org/I30181195"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Yusuke Yamamoto","raw_affiliation_strings":["School of Pharmaceutical Sciences, Ohu University, 31\u20131 Misumido, Tomita-machi, Koriyama, Fukushima 963\u20138041, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"School of Pharmaceutical Sciences, Ohu University, 31\u20131 Misumido, Tomita-machi, Koriyama, Fukushima 963\u20138041, Japan","institution_ids":["https://openalex.org/I30181195"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5088285092","display_name":"Hidetomo Kikuchi","orcid":"https://orcid.org/0000-0002-7704-4859","observed_orcids":["https://orcid.org/0000-0002-7704-4859"]},"institutions":[{"id":"https://openalex.org/I201389808","display_name":"Josai University","ror":"https://ror.org/021r6aq66","country_code":"JP","type":"education","lineage":["https://openalex.org/I201389808"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Hidetomo Kikuchi","raw_affiliation_strings":["Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, 1\u20131 Keyakidai, Sakado, Saitama 350\u20130295, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, 1\u20131 Keyakidai, Sakado, Saitama 350\u20130295, Japan","institution_ids":["https://openalex.org/I201389808"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5016660479","display_name":"Rie Arai","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I190930483","display_name":"Kyorin University","ror":"https://ror.org/0188yz413","country_code":"JP","type":"education","lineage":["https://openalex.org/I190930483"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Rie Arai","raw_affiliation_strings":["School of Medicine, Kyorin University, 6\u201320\u20132 Shinkawa, Mitaka, Tokyo 181\u20138611, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"School of Medicine, Kyorin University, 6\u201320\u20132 Shinkawa, Mitaka, Tokyo 181\u20138611, Japan","institution_ids":["https://openalex.org/I190930483"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5052042290","display_name":"Yuki Toguchi","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I201389808","display_name":"Josai University","ror":"https://ror.org/021r6aq66","country_code":"JP","type":"education","lineage":["https://openalex.org/I201389808"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Yuki Toguchi","raw_affiliation_strings":["Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, 1\u20131 Keyakidai, Sakado, Saitama 350\u20130295, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, 1\u20131 Keyakidai, Sakado, Saitama 350\u20130295, Japan","institution_ids":["https://openalex.org/I201389808"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5152680214","display_name":"Bo Yuan","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I201389808","display_name":"Josai University","ror":"https://ror.org/021r6aq66","country_code":"JP","type":"education","lineage":["https://openalex.org/I201389808"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Bo Yuan","raw_affiliation_strings":["Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, 1\u20131 Keyakidai, Sakado, Saitama 350\u20130295, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, 1\u20131 Keyakidai, Sakado, Saitama 350\u20130295, Japan","institution_ids":["https://openalex.org/I201389808"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5110776612","display_name":"Katsuyoshi Sunaga","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I201389808","display_name":"Josai University","ror":"https://ror.org/021r6aq66","country_code":"JP","type":"education","lineage":["https://openalex.org/I201389808"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Katsuyoshi Sunaga","raw_affiliation_strings":["Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, 1\u20131 Keyakidai, Sakado, Saitama 350\u20130295, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, 1\u20131 Keyakidai, Sakado, Saitama 350\u20130295, Japan","institution_ids":["https://openalex.org/I201389808"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":3,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":null,"apc_paid":null,"fwci":0.0,"has_fulltext":true,"cited_by_count":0,"citation_normalized_percentile":{"value":0.57241229,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":null,"biblio":{"volume":"74","issue":"9","first_page":"723","last_page":"729"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10274","display_name":"Heterocyclic Compound Synthesis and Bioactivity","score":0.8241999745368958,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T10274","display_name":"Heterocyclic Compound Synthesis and Bioactivity","score":0.8241999745368958,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T14099","display_name":"Synthesis and Characterization of Heterocyclic Compounds","score":0.0771000012755394,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T13208","display_name":"Synthesis of heterocyclic compounds","score":0.0471000000834465,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/tautomerism","display_name":"tautomerism","score":0.9610000252723694},{"id":"https://openalex.org/keywords/heterocycle-synthesis","display_name":"heterocyclic synthesis","score":0.6990000009536743},{"id":"https://openalex.org/keywords/bioactivity","display_name":"biological activity","score":0.9269999861717224}],"concepts":[{"id":"https://openalex.org/C116073593","wikidata":"https://www.wikidata.org/wiki/Q864491","display_name":"Biological activity","level":3,"score":0.654699981212616},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.6146000027656555},{"id":"https://openalex.org/C111233374","wikidata":"https://www.wikidata.org/wiki/Q334640","display_name":"Tautomer","level":2,"score":0.5138999819755554},{"id":"https://openalex.org/C2985495968","wikidata":"https://www.wikidata.org/wiki/Q422453","display_name":"Motor activity","level":2,"score":0.29789999127388},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.26089999079704285},{"id":"https://openalex.org/C116834253","wikidata":"https://www.wikidata.org/wiki/Q2039217","display_name":"Identification (biology)","level":2,"score":0.23749999701976776},{"id":"https://openalex.org/C2780791683","wikidata":"https://www.wikidata.org/wiki/Q846785","display_name":"Action (physics)","level":2,"score":0.23589999973773956},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.2159000039100647},{"id":"https://openalex.org/C193042331","wikidata":"https://www.wikidata.org/wiki/Q1772003","display_name":"Structure\u2013activity relationship","level":3,"score":0.1972000002861023},{"id":"https://openalex.org/C527412718","wikidata":"https://www.wikidata.org/wiki/Q855395","display_name":"Interpretation (philosophy)","level":2,"score":0.19249999523162842}],"mesh":[{"descriptor_ui":"D000970","descriptor_name":"Antineoplastic Agents","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D000970","descriptor_name":"Antineoplastic Agents","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":true},{"descriptor_ui":"D000970","descriptor_name":"Antineoplastic Agents","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D004305","descriptor_name":"Dose-Response Relationship, Drug","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D004354","descriptor_name":"Drug Screening Assays, Antitumor","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D006801","descriptor_name":"Humans","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D011743","descriptor_name":"Pyrimidines","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D011743","descriptor_name":"Pyrimidines","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":true},{"descriptor_ui":"D011743","descriptor_name":"Pyrimidines","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D013329","descriptor_name":"Structure-Activity Relationship","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D049109","descriptor_name":"Cell Proliferation","qualifier_ui":"Q000187","qualifier_name":"drug effects","is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1248/cpb.c26-00391","doi":"https://doi.org/10.1248/cpb.c26-00391","is_oa":true,"landing_page_url":"https://doi.org/10.1248/cpb.c26-00391","pdf_url":"https://www.jstage.jst.go.jp/article/cpb/74/9/74_c26-00391/_pdf","source":{"id":"https://openalex.org/S3861430","display_name":"Chemical and Pharmaceutical Bulletin","issn_l":"0009-2363","issn":["0009-2363","1347-5223"],"is_oa":true,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-c","jufo-1","medline","norway-1","poland-40","russia-white-list-2"],"host_organization":"https://openalex.org/P4310313382","host_organization_name":"Pharmaceutical Society of Japan","host_organization_lineage":["https://openalex.org/P4310313382"],"host_organization_lineage_names":["Pharmaceutical Society of Japan"],"type":"journal"},"license":"cc-by-nc","license_id":"https://openalex.org/licenses/cc-by-nc","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chemical and Pharmaceutical Bulletin","raw_type":"journal-article"},{"id":"pmid:42802044","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/42802044","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chemical & pharmaceutical bulletin","raw_type":"Journal Article"}],"best_oa_location":{"id":"doi:10.1248/cpb.c26-00391","doi":"https://doi.org/10.1248/cpb.c26-00391","is_oa":true,"landing_page_url":"https://doi.org/10.1248/cpb.c26-00391","pdf_url":"https://www.jstage.jst.go.jp/article/cpb/74/9/74_c26-00391/_pdf","source":{"id":"https://openalex.org/S3861430","display_name":"Chemical and Pharmaceutical Bulletin","issn_l":"0009-2363","issn":["0009-2363","1347-5223"],"is_oa":true,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-c","jufo-1","medline","norway-1","poland-40","russia-white-list-2"],"host_organization":"https://openalex.org/P4310313382","host_organization_name":"Pharmaceutical Society of Japan","host_organization_lineage":["https://openalex.org/P4310313382"],"host_organization_lineage_names":["Pharmaceutical Society of Japan"],"type":"journal"},"license":"cc-by-nc","license_id":"https://openalex.org/licenses/cc-by-nc","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chemical and Pharmaceutical Bulletin","raw_type":"journal-article"},"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[{"id":"https://openalex.org/F4320334764","display_name":"Japan Society for the Promotion of Science","ror":"https://ror.org/00hhkn466"}],"has_content":{"pdf":true,"grobid_xml":true},"content_urls":{"pdf":"https://content.openalex.org/works/W7214214745.pdf","grobid_xml":"https://content.openalex.org/works/W7214214745.grobid-xml"},"referenced_works_count":0,"referenced_works":[],"related_works":["https://openalex.org/W4399201713","https://openalex.org/W3128404158","https://openalex.org/W3011249442","https://openalex.org/W2008367320","https://openalex.org/W3084074164","https://openalex.org/W3022212280","https://openalex.org/W2007957580","https://openalex.org/W2083942183","https://openalex.org/W3138706810","https://openalex.org/W1982357319"],"abstract_inverted_index":{"Dihydropyrimidines":[0],"(DPs)":[1],"show":[2,20],"a":[3,37,42,74,126,155],"wide":[4],"range":[5],"of":[6,51,65,73,76,90,95,102,107,112],"biological":[7,165],"activities":[8],"for":[9,121],"medicinal":[10],"applications.":[11],"Among":[12],"DP":[13],"derivatives,":[14],"2-aryl-DPs":[15],"have":[16],"been":[17],"reported":[18],"to":[19,163],"remarkable":[21],"pharmacological":[22],"properties.":[23],"In":[24],"this":[25],"work,":[26],"6-unsubstituted,":[27],"N-unsubstituted":[28],"2-aryl-1,4-DP":[29],"and":[30,41,54,114,140,157],"its":[31],"1,6-DP":[32,56,96],"tautomer":[33],"were":[34,118,144],"synthesized":[35],"using":[36],"Pd2dba3/(2-furyl)3P-catalyzed,":[38],"CuCl-mediated":[39],"2-arylation":[40],"deprotection":[43],"reaction.":[44],"The":[45,81,147],"sequential":[46],"reactions":[47],"give":[48],"twenty":[49],"types":[50],"the":[52,55,63,77,87,93,99,105,110,151,158,164],"1,4-DP":[53,108,113],"tautomers":[57,78],"in":[58],"high":[59,137],"yields.":[60],"To":[61],"clarify":[62],"effects":[64],"substituents":[66,91,103],"on":[67,125],"their":[68,122,141],"tautomeric":[69],"behavior,":[70],"1H-NMR":[71],"analysis":[72,82,148],"mixture":[75],"was":[79],"performed.":[80],"revealed":[83],"that":[84,150],"not":[85],"only":[86],"electronic":[88,100],"properties":[89,101],"at":[92,104],"2-position":[94],"but":[97],"also":[98,119],"4-position":[106],"affect":[109],"stability":[111],"1,6-DP.":[115],"These":[116],"compounds":[117,134],"assessed":[120],"antiproliferative":[123],"effect":[124],"human":[127],"promyelocytic":[128],"leukemia":[129],"cell":[130],"line,":[131],"HL-60.":[132],"Five":[133],"showed":[135],"relatively":[136],"inhibitory":[138],"activity,":[139],"IC50":[142],"values":[143],"1.7\u20133.9":[145],"\u03bcM.":[146],"indicates":[149],"2-aryl":[152],"group":[153,160],"with":[154],"para-substituent":[156],"cyclohexyl":[159],"are":[161],"related":[162],"activity.":[166]},"counts_by_year":[],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2026-09-25T00:00:00"}