{"id":"https://openalex.org/W1573408757","doi":"https://doi.org/10.1248/cpb.29.116","title":"Antitumor activity of shikonin, alkannin and their derivatives. II. X-ray analysis of cyclo-alkannin leucoacetate, tautomerism of alkannin and cyclo-alkannin and antitumor activity of alkannin derivatives.","display_name":"Antitumor activity of shikonin, alkannin and their derivatives. II. X-ray analysis of cyclo-alkannin leucoacetate, tautomerism of alkannin and cyclo-alkannin and antitumor activity of alkannin derivatives.","publication_year":1981,"publication_date":"1981-01-01","ids":{"openalex":"https://openalex.org/W1573408757","doi":"https://doi.org/10.1248/cpb.29.116","mag":"1573408757","pmid":"https://pubmed.ncbi.nlm.nih.gov/7261189"},"language":"en","primary_location":{"id":"doi:10.1248/cpb.29.116","doi":"https://doi.org/10.1248/cpb.29.116","is_oa":true,"landing_page_url":"https://doi.org/10.1248/cpb.29.116","pdf_url":"https://www.jstage.jst.go.jp/article/cpb1958/29/1/29_1_116/_pdf","source":{"id":"https://openalex.org/S3861430","display_name":"Chemical and Pharmaceutical Bulletin","issn_l":"0009-2363","issn":["0009-2363","1347-5223"],"is_oa":false,"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":null,"license_id":null,"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":"bronze","oa_url":"https://www.jstage.jst.go.jp/article/cpb1958/29/1/29_1_116/_pdf","any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5079329420","display_name":"Ushio Sankawa","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I74801974","display_name":"The University of Tokyo","ror":"https://ror.org/057zh3y96","country_code":"JP","type":"education","lineage":["https://openalex.org/I74801974"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"USHIO SANKAWA","raw_affiliation_strings":["/, / Faculty of Pharmaceutical Sciences, University of Tokyo, / National Cancer Center Institute"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"/, / Faculty of Pharmaceutical Sciences, University of Tokyo, / National Cancer Center Institute","institution_ids":["https://openalex.org/I74801974"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5075826513","display_name":"Hideaki Otsuka","orcid":"https://orcid.org/0000-0002-7637-7635","observed_orcids":["https://orcid.org/0000-0002-7637-7635"]},"institutions":[{"id":"https://openalex.org/I74801974","display_name":"The University of Tokyo","ror":"https://ror.org/057zh3y96","country_code":"JP","type":"education","lineage":["https://openalex.org/I74801974"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"HIDEAKI OTSUKA","raw_affiliation_strings":["/, / Faculty of Pharmaceutical Sciences, University of Tokyo, / National Cancer Center Institute"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"/, / Faculty of Pharmaceutical Sciences, University of Tokyo, / National Cancer Center Institute","institution_ids":["https://openalex.org/I74801974"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5062103708","display_name":"YOSHITOMO KATAOKA","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I74801974","display_name":"The University of Tokyo","ror":"https://ror.org/057zh3y96","country_code":"JP","type":"education","lineage":["https://openalex.org/I74801974"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"YOSHITOMO KATAOKA","raw_affiliation_strings":["/, / Faculty of Pharmaceutical Sciences, University of Tokyo, / National Cancer Center Institute"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"/, / Faculty of Pharmaceutical Sciences, University of Tokyo, / National Cancer Center Institute","institution_ids":["https://openalex.org/I74801974"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5109994478","display_name":"Y\u00f6ichi Iitaka","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I74801974","display_name":"The University of Tokyo","ror":"https://ror.org/057zh3y96","country_code":"JP","type":"education","lineage":["https://openalex.org/I74801974"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"YOICHI IITAKA","raw_affiliation_strings":["/, / Faculty of Pharmaceutical Sciences, University of Tokyo, / National Cancer Center Institute"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"/, / Faculty of Pharmaceutical Sciences, University of Tokyo, / National Cancer Center Institute","institution_ids":["https://openalex.org/I74801974"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5061123773","display_name":"Akio Hoshi","orcid":"https://orcid.org/0000-0002-9989-2285","observed_orcids":["https://orcid.org/0000-0002-9989-2285"]},"institutions":[{"id":"https://openalex.org/I74801974","display_name":"The University of Tokyo","ror":"https://ror.org/057zh3y96","country_code":"JP","type":"education","lineage":["https://openalex.org/I74801974"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"AKIO HOSHI","raw_affiliation_strings":["/, / Faculty of Pharmaceutical Sciences, University of Tokyo, / National Cancer Center Institute"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"/, / Faculty of Pharmaceutical Sciences, University of Tokyo, / National Cancer Center Institute","institution_ids":["https://openalex.org/I74801974"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5004509765","display_name":"Kazuo Kuretani","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I74801974","display_name":"The University of Tokyo","ror":"https://ror.org/057zh3y96","country_code":"JP","type":"education","lineage":["https://openalex.org/I74801974"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"KAZUO KURETANI","raw_affiliation_strings":["/, / Faculty of Pharmaceutical Sciences, University of Tokyo, / National Cancer Center Institute"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"/, / Faculty of Pharmaceutical Sciences, University of Tokyo, / National Cancer Center Institute","institution_ids":["https://openalex.org/I74801974"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I74801974"],"apc_list":null,"apc_paid":null,"fwci":1.152,"has_fulltext":false,"cited_by_count":53,"citation_normalized_percentile":{"value":0.72278261,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":87,"max":97},"biblio":{"volume":"29","issue":"1","first_page":"116","last_page":"122"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12356","display_name":"Bioactive Compounds and Antitumor Agents","score":0.9916999936103821,"subfield":{"id":"https://openalex.org/subfields/3005","display_name":"Toxicology"},"field":{"id":"https://openalex.org/fields/30","display_name":"Pharmacology, Toxicology and Pharmaceutics"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},"topics":[{"id":"https://openalex.org/T12356","display_name":"Bioactive Compounds and Antitumor Agents","score":0.9916999936103821,"subfield":{"id":"https://openalex.org/subfields/3005","display_name":"Toxicology"},"field":{"id":"https://openalex.org/fields/30","display_name":"Pharmacology, Toxicology and Pharmaceutics"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T10274","display_name":"Heterocyclic Compound Synthesis and Bioactivity","score":0.0008999999845400453,"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/T12653","display_name":"Cyclization and Aryne Chemistry","score":0.0006000000284984708,"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/shikonin","display_name":"shikonin","score":0.9860000014305115},{"id":"https://openalex.org/keywords/alkannin","display_name":"alkannin","score":0.9990000128746033},{"id":"https://openalex.org/keywords/tautomerism","display_name":"tautomerism","score":0.7440000176429749},{"id":"https://openalex.org/keywords/cyclization","display_name":"cyclization","score":0.6100000143051147},{"id":"https://openalex.org/keywords/crystal-structure","display_name":"crystal structure","score":0.625},{"id":"https://openalex.org/keywords/anticancer-activity","display_name":"anticancer activity","score":0.8970000147819519},{"id":"https://openalex.org/keywords/shikonin-derivatives","display_name":"shikonin derivatives","score":0.640999972820282}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8801784515380859},{"id":"https://openalex.org/C111233374","wikidata":"https://www.wikidata.org/wiki/Q334640","display_name":"Tautomer","level":2,"score":0.644941508769989},{"id":"https://openalex.org/C2780643102","wikidata":"https://www.wikidata.org/wiki/Q412382","display_name":"Quinone","level":2,"score":0.5470503568649292},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.472013920545578},{"id":"https://openalex.org/C2780378348","wikidata":"https://www.wikidata.org/wiki/Q25351438","display_name":"Ring (chemistry)","level":2,"score":0.4390043318271637},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.25949764251708984}],"mesh":[{"descriptor_ui":"D000818","descriptor_name":"Animals","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D000972","descriptor_name":"Antineoplastic Agents, Phytogenic","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D009284","descriptor_name":"Naphthols","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":true},{"descriptor_ui":"D009285","descriptor_name":"Naphthoquinones","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":true},{"descriptor_ui":"D013237","descriptor_name":"Stereoisomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D014961","descriptor_name":"X-Ray Diffraction","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D051379","descriptor_name":"Mice","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":3,"locations":[{"id":"doi:10.1248/cpb.29.116","doi":"https://doi.org/10.1248/cpb.29.116","is_oa":true,"landing_page_url":"https://doi.org/10.1248/cpb.29.116","pdf_url":"https://www.jstage.jst.go.jp/article/cpb1958/29/1/29_1_116/_pdf","source":{"id":"https://openalex.org/S3861430","display_name":"Chemical and Pharmaceutical Bulletin","issn_l":"0009-2363","issn":["0009-2363","1347-5223"],"is_oa":false,"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":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chemical and Pharmaceutical Bulletin","raw_type":"journal-article"},{"id":"pmid:7261189","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/7261189","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"},{"id":"mag:3145974707","doi":null,"is_oa":false,"landing_page_url":"http://jglobal.jst.go.jp/public/20090422/200902029230161941","pdf_url":null,"source":{"id":"https://openalex.org/S3861430","display_name":"Chemical and Pharmaceutical Bulletin","issn_l":"0009-2363","issn":["0009-2363","1347-5223"],"is_oa":false,"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":null,"license_id":null,"version":null,"is_accepted":false,"is_published":false,"raw_source_name":"Chemical and Pharmaceutical Bulletin","raw_type":null}],"best_oa_location":{"id":"doi:10.1248/cpb.29.116","doi":"https://doi.org/10.1248/cpb.29.116","is_oa":true,"landing_page_url":"https://doi.org/10.1248/cpb.29.116","pdf_url":"https://www.jstage.jst.go.jp/article/cpb1958/29/1/29_1_116/_pdf","source":{"id":"https://openalex.org/S3861430","display_name":"Chemical and Pharmaceutical Bulletin","issn_l":"0009-2363","issn":["0009-2363","1347-5223"],"is_oa":false,"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":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chemical and Pharmaceutical Bulletin","raw_type":"journal-article"},"sustainable_development_goals":[{"id":"https://metadata.un.org/sdg/3","display_name":"Good health and well-being","score":0.4000000059604645}],"study_designs":[],"awards":[],"funders":[],"has_content":{"pdf":true,"grobid_xml":true},"content_urls":{"pdf":"https://content.openalex.org/works/W1573408757.pdf","grobid_xml":"https://content.openalex.org/works/W1573408757.grobid-xml"},"referenced_works_count":1,"referenced_works":["https://openalex.org/W1501885095"],"related_works":["https://openalex.org/W4220772158","https://openalex.org/W2157975964","https://openalex.org/W2949160020","https://openalex.org/W4231649015","https://openalex.org/W2314869271","https://openalex.org/W2094647388","https://openalex.org/W2152071982","https://openalex.org/W1988924492","https://openalex.org/W2514810041","https://openalex.org/W2029209763"],"abstract_inverted_index":{"Cyclo-alkannin":[0],"and":[1,14,61,70,73,87,100,107,139],"cycloshikonin":[2],"were":[3],"formerly":[4],"considered":[5],"to":[6],"be":[7,123],"derivatives":[8,141],"of":[9,28,52,59,79,97,105,114,127,134],"hydroanthraquinone":[10],"3.":[11],"However,":[12],"chemical":[13,109],"spectral":[15],"investigation":[16],"revealed":[17],"that":[18,119],"cycloalkannin":[19,140],"possesses":[20],"no":[21],"secondary":[22],"hydroxyl":[23,68],"group.":[24],"Thus,":[25],"the":[26,38,42,67,77,95,98,115],"structure":[27],"cyclo-alkannin":[29,88],"leucoacetate":[30],"(8)":[31],"was":[32,55],"determined":[33],"by":[34,37],"X-ray":[35],"analysis,":[36],"direct":[39],"method":[40],";":[41],"final":[43],"R":[44],"index":[45],"with":[46],"hydrogen":[47],"atoms":[48],"except":[49],"for":[50],"those":[51],"methyl":[53],"groups":[54],"0.065.":[56],"The":[57,103,132],"cyclization":[58],"alkannin":[60,86,138],"shikonin":[62],"is":[63],"a":[64,80],"reaction":[65],"between":[66],"group":[69],"double":[71],"bond":[72],"does":[74],"not":[75],"involve":[76],"formation":[78],"carbocyclic":[81],"ring.":[82],"In":[83],"1H-NMR":[84],"both":[85],"show":[89],"two":[90],"singlet":[91],"signals":[92],"arising":[93],"from":[94],"protons":[96],"aromatic":[99],"quinonic":[101,116],"rings.":[102],"absence":[104],"coupling":[106],"lower":[108],"shift":[110],"values":[111],"suggests":[112],"delocalization":[113],"ring":[117],"so":[118],"these":[120],"compounds":[121],"can":[122],"regarded":[124],"as":[125],"consisting":[126],"tautomeric":[128],"structures":[129],"(10,":[130],"11).":[131],"results":[133],"antitumor":[135],"tests":[136],"on":[137],"(6,":[142],"7,":[143],"8,":[144],"10,":[145],"11)":[146],"are":[147],"also":[148],"reported.":[149]},"counts_by_year":[{"year":2022,"cited_by_count":1},{"year":2021,"cited_by_count":1},{"year":2020,"cited_by_count":3},{"year":2017,"cited_by_count":2},{"year":2016,"cited_by_count":1},{"year":2014,"cited_by_count":4},{"year":2013,"cited_by_count":3}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}