{"id":"https://openalex.org/W1994881013","doi":"https://doi.org/10.1021/np50022a004","title":"Synthesis of Naphthoquinoles as Potential Antitumor Agents Related to Jacaranone","display_name":"Synthesis of Naphthoquinoles as Potential Antitumor Agents Related to Jacaranone","publication_year":1982,"publication_date":"1982-07-01","ids":{"openalex":"https://openalex.org/W1994881013","doi":"https://doi.org/10.1021/np50022a004","mag":"1994881013","pmid":"https://pubmed.ncbi.nlm.nih.gov/7130984"},"language":"en","primary_location":{"id":"doi:10.1021/np50022a004","doi":"https://doi.org/10.1021/np50022a004","is_oa":false,"landing_page_url":"https://doi.org/10.1021/np50022a004","pdf_url":null,"source":{"id":"https://openalex.org/S166799026","display_name":"Journal of Natural Products","issn_l":"0163-3864","issn":["0163-3864","1520-6025"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-b","doyens","jufo-1","ki-jl-1","medline","norway-2","poland-100","russia-white-list-1"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Natural Products","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5110276129","display_name":"Howard M. Deutsch","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Howard M. Deutsch","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"last","author":{"id":"https://openalex.org/A5025743988","display_name":"Leon H. Zalkow","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Leon H. Zalkow","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]}],"institutions":[],"countries_distinct_count":0,"institutions_distinct_count":0,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":0.0,"has_fulltext":false,"cited_by_count":2,"citation_normalized_percentile":{"value":0.06989247,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":null,"biblio":{"volume":"45","issue":"4","first_page":"390","last_page":"392"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12356","display_name":"Bioactive Compounds and Antitumor Agents","score":0.9771000146865845,"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":0.9771000146865845,"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/T12653","display_name":"Cyclization and Aryne Chemistry","score":0.006200000178068876,"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/T10274","display_name":"Heterocyclic Compound Synthesis and Bioactivity","score":0.003000000026077032,"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/naphthoquinones","display_name":"naphthoquinones","score":0.921999990940094},{"id":"https://openalex.org/keywords/anticancer-agents","display_name":"anticancer agents","score":0.9629999995231628},{"id":"https://openalex.org/keywords/trimethylsilyl-cyanide","display_name":"trimethylsilyl cyanide","score":0.8220000267028809},{"id":"https://openalex.org/keywords/carbonyl-protection","display_name":"carbonyl protection","score":0.7630000114440918},{"id":"https://openalex.org/keywords/cytotoxicity","display_name":"cytotoxicity","score":0.9879999756813049}],"concepts":[{"id":"https://openalex.org/C109316439","wikidata":"https://www.wikidata.org/wiki/Q246181","display_name":"Cytotoxicity","level":3,"score":0.7203588485717773},{"id":"https://openalex.org/C94412978","wikidata":"https://www.wikidata.org/wiki/Q103135","display_name":"Hydrolysis","level":2,"score":0.6817288398742676},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.6655349731445312},{"id":"https://openalex.org/C184651966","wikidata":"https://www.wikidata.org/wiki/Q906356","display_name":"Aqueous solution","level":2,"score":0.5794910192489624},{"id":"https://openalex.org/C2780828025","wikidata":"https://www.wikidata.org/wiki/Q44793182","display_name":"Fluoride","level":2,"score":0.4800601899623871},{"id":"https://openalex.org/C114373084","wikidata":"https://www.wikidata.org/wiki/Q273499","display_name":"Chemical synthesis","level":3,"score":0.46373334527015686},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.46034979820251465},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.4180334508419037},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.3782063126564026},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.19972383975982666},{"id":"https://openalex.org/C202751555","wikidata":"https://www.wikidata.org/wiki/Q221681","display_name":"In vitro","level":2,"score":0.18754878640174866},{"id":"https://openalex.org/C179104552","wikidata":"https://www.wikidata.org/wiki/Q11165","display_name":"Inorganic chemistry","level":1,"score":0.0}],"mesh":[{"descriptor_ui":"D000970","descriptor_name":"Antineoplastic Agents","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D002478","descriptor_name":"Cells, Cultured","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":"D009285","descriptor_name":"Naphthoquinones","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D009285","descriptor_name":"Naphthoquinones","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":false},{"descriptor_ui":"D009303","descriptor_name":"Nasopharyngeal Neoplasms","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D009374","descriptor_name":"Neoplasms, Experimental","qualifier_ui":"Q000188","qualifier_name":"drug therapy","is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/np50022a004","doi":"https://doi.org/10.1021/np50022a004","is_oa":false,"landing_page_url":"https://doi.org/10.1021/np50022a004","pdf_url":null,"source":{"id":"https://openalex.org/S166799026","display_name":"Journal of Natural Products","issn_l":"0163-3864","issn":["0163-3864","1520-6025"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-b","doyens","jufo-1","ki-jl-1","medline","norway-2","poland-100","russia-white-list-1"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Natural Products","raw_type":"journal-article"},{"id":"pmid:7130984","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/7130984","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":"Journal of natural products","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[{"display_name":"Good health and well-being","id":"https://metadata.un.org/sdg/3","score":0.428600013256073}],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":0,"referenced_works":[],"related_works":["https://openalex.org/W2031646840","https://openalex.org/W4408606377","https://openalex.org/W2115993189","https://openalex.org/W2412817727","https://openalex.org/W2954733543","https://openalex.org/W2417894862","https://openalex.org/W2156701186","https://openalex.org/W2075699403","https://openalex.org/W2014317460","https://openalex.org/W2789329237"],"abstract_inverted_index":{"Naphthoquinols":[0],"3a,":[1],"3b":[2],"and":[3,29,41,67],"3c":[4],"were":[5,63],"synthesized":[6],"from":[7],"the":[8,12,24,58],"corresponding":[9],"naphthoquinones":[10],"by":[11],"series":[13],"of":[14,17,26,47,49],"reactions,":[15],"protection":[16],"one":[18,48],"carbonyl":[19],"with":[20,23,32],"trimethylsilycyanide,":[21],"reaction":[22],"enolate":[25],"methyl":[27],"acetate,":[28],"hydrolytic":[30],"deprotection":[31],"aqueous":[33],"silver":[34],"fluoride.":[35],"The":[36],"unusual":[37],"internal":[38],"hemiketals":[39],"4a":[40],"4b":[42],"appeared":[43],"to":[44,57,69],"be":[45,70],"byproducts":[46],"these":[50],"reactions.":[51],"These":[52],"naphthoquinols,":[53],"which":[54],"are":[55],"related":[56],"antitumor":[59],"compound":[60],"jacaranone":[61],"(1a),":[62],"tested":[64],"for":[65],"cytotoxicity":[66],"found":[68],"inactive.":[71]},"counts_by_year":[],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}
