{"id":"https://openalex.org/W2013141013","doi":"https://doi.org/10.1021/jo0303822","title":"A Highly Abbreviated Synthesis of Dibenzo[def,p]chrysene and Its 12-Methoxy Derivative, a Key Precursor for the Synthesis of the Proximate and Ultimate Carcinogens of Dibenzo[def,p]chrysene","display_name":"A Highly Abbreviated Synthesis of Dibenzo[def,p]chrysene and Its 12-Methoxy Derivative, a Key Precursor for the Synthesis of the Proximate and Ultimate Carcinogens of Dibenzo[def,p]chrysene","publication_year":2004,"publication_date":"2004-04-28","ids":{"openalex":"https://openalex.org/W2013141013","doi":"https://doi.org/10.1021/jo0303822","mag":"2013141013","pmid":"https://pubmed.ncbi.nlm.nih.gov/15153038"},"language":"en","primary_location":{"id":"doi:10.1021/jo0303822","doi":"https://doi.org/10.1021/jo0303822","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo0303822","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"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":"The Journal of Organic Chemistry","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/A5001311093","display_name":"Arun Kumar Sharma","orcid":"https://orcid.org/0000-0002-7679-7779","observed_orcids":["https://orcid.org/0000-0002-7679-7779","https://orcid.org/0000-0002-5191-7738","https://orcid.org/0000-0001-9427-6208"]},"institutions":[{"id":"https://openalex.org/I1327163397","display_name":"State University of New York","ror":"https://ror.org/01q1z8k08","country_code":"US","type":"education","lineage":["https://openalex.org/I1327163397"]},{"id":"https://openalex.org/I4210167017","display_name":"Institute for Cancer Prevention","ror":"https://ror.org/05t7jxa31","country_code":"US","type":"other","lineage":["https://openalex.org/I4210167017"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Arun K. Sharma","raw_affiliation_strings":["Institute for Cancer Prevention, American Health Foundation Cancer Center, 1 Dana Road, Valhalla, New York 10595, and Environmental Toxicology and Chemistry Laboratory, Great Lakes Center, State University of New York College at Buffalo, 1300 Elmwood Avenue, Buffalo, New York 14222 asharma@ifcp.us"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Institute for Cancer Prevention, American Health Foundation Cancer Center, 1 Dana Road, Valhalla, New York 10595, and Environmental Toxicology and Chemistry Laboratory, Great Lakes Center, State University of New York College at Buffalo, 1300 Elmwood Avenue, Buffalo, New York 14222 asharma@ifcp.us","institution_ids":["https://openalex.org/I1327163397","https://openalex.org/I4210167017"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5079782739","display_name":"Subodh Kumar","orcid":"https://orcid.org/0000-0001-8872-2785","observed_orcids":["https://orcid.org/0000-0001-8872-2785"]},"institutions":[{"id":"https://openalex.org/I1327163397","display_name":"State University of New York","ror":"https://ror.org/01q1z8k08","country_code":"US","type":"education","lineage":["https://openalex.org/I1327163397"]},{"id":"https://openalex.org/I4210167017","display_name":"Institute for Cancer Prevention","ror":"https://ror.org/05t7jxa31","country_code":"US","type":"other","lineage":["https://openalex.org/I4210167017"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Subodh Kumar","raw_affiliation_strings":["Institute for Cancer Prevention, American Health Foundation Cancer Center, 1 Dana Road, Valhalla, New York 10595, and Environmental Toxicology and Chemistry Laboratory, Great Lakes Center, State University of New York College at Buffalo, 1300 Elmwood Avenue, Buffalo, New York 14222 asharma@ifcp.us"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Institute for Cancer Prevention, American Health Foundation Cancer Center, 1 Dana Road, Valhalla, New York 10595, and Environmental Toxicology and Chemistry Laboratory, Great Lakes Center, State University of New York College at Buffalo, 1300 Elmwood Avenue, Buffalo, New York 14222 asharma@ifcp.us","institution_ids":["https://openalex.org/I1327163397","https://openalex.org/I4210167017"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5048058203","display_name":"Shantu Amin","orcid":"https://orcid.org/0000-0003-2780-2567","observed_orcids":["https://orcid.org/0000-0003-2780-2567"]},"institutions":[{"id":"https://openalex.org/I1327163397","display_name":"State University of New York","ror":"https://ror.org/01q1z8k08","country_code":"US","type":"education","lineage":["https://openalex.org/I1327163397"]},{"id":"https://openalex.org/I4210167017","display_name":"Institute for Cancer Prevention","ror":"https://ror.org/05t7jxa31","country_code":"US","type":"other","lineage":["https://openalex.org/I4210167017"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Shantu Amin","raw_affiliation_strings":["Institute for Cancer Prevention, American Health Foundation Cancer Center, 1 Dana Road, Valhalla, New York 10595, and Environmental Toxicology and Chemistry Laboratory, Great Lakes Center, State University of New York College at Buffalo, 1300 Elmwood Avenue, Buffalo, New York 14222 asharma@ifcp.us"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Institute for Cancer Prevention, American Health Foundation Cancer Center, 1 Dana Road, Valhalla, New York 10595, and Environmental Toxicology and Chemistry Laboratory, Great Lakes Center, State University of New York College at Buffalo, 1300 Elmwood Avenue, Buffalo, New York 14222 asharma@ifcp.us","institution_ids":["https://openalex.org/I1327163397","https://openalex.org/I4210167017"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":0.6317,"has_fulltext":false,"cited_by_count":30,"citation_normalized_percentile":{"value":0.62852068,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":96},"biblio":{"volume":"69","issue":"11","first_page":"3979","last_page":"3982"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10548","display_name":"Catalytic Cross-Coupling Reactions","score":0.7631999850273132,"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/T10548","display_name":"Catalytic Cross-Coupling Reactions","score":0.7631999850273132,"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/T11298","display_name":"Synthesis and Properties of Aromatic Compounds","score":0.07370000332593918,"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/T10354","display_name":"Catalytic C\u2013H Functionalization Methods","score":0.04089999943971634,"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/polycyclic-aromatic-hydrocarbons","display_name":"polycyclic aromatic hydrocarbons","score":0.9049999713897705},{"id":"https://openalex.org/keywords/suzuki-miyaura-coupling","display_name":"Suzuki coupling","score":0.9789999723434448},{"id":"https://openalex.org/keywords/ultimate-carcinogens","display_name":"ultimate carcinogens","score":0.6169999837875366},{"id":"https://openalex.org/keywords/proximate-carcinogens","display_name":"proximate carcinogens","score":0.8019999861717224},{"id":"https://openalex.org/keywords/metabolic-activation","display_name":"metabolic activation","score":0.6449999809265137},{"id":"https://openalex.org/keywords/dna-adducts","display_name":"DNA adducts","score":0.6230000257492065},{"id":"https://openalex.org/keywords/mutagenicity","display_name":"mutagenicity","score":0.8230000138282776},{"id":"https://openalex.org/keywords/tumor-induction","display_name":"tumor induction","score":0.5690000057220459}],"concepts":[{"id":"https://openalex.org/C2775959351","wikidata":"https://www.wikidata.org/wiki/Q415465","display_name":"Chrysene","level":3,"score":0.9786120057106018},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9265422821044922},{"id":"https://openalex.org/C193523891","wikidata":"https://www.wikidata.org/wiki/Q1771950","display_name":"dBc","level":3,"score":0.8980555534362793},{"id":"https://openalex.org/C114246631","wikidata":"https://www.wikidata.org/wiki/Q187661","display_name":"Carcinogen","level":2,"score":0.5916547775268555},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5841302871704102},{"id":"https://openalex.org/C2777477808","wikidata":"https://www.wikidata.org/wiki/Q407595","display_name":"Metabolite","level":2,"score":0.5665493011474609},{"id":"https://openalex.org/C111771559","wikidata":"https://www.wikidata.org/wiki/Q66295","display_name":"Derivative (finance)","level":2,"score":0.5507859587669373},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.20401525497436523},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.1472753882408142},{"id":"https://openalex.org/C2778951431","wikidata":"https://www.wikidata.org/wiki/Q415723","display_name":"Pyrene","level":2,"score":0.14311668276786804},{"id":"https://openalex.org/C106159729","wikidata":"https://www.wikidata.org/wiki/Q2294553","display_name":"Financial economics","level":1,"score":0.0},{"id":"https://openalex.org/C89631360","wikidata":"https://www.wikidata.org/wiki/Q1428766","display_name":"Phase noise","level":2,"score":0.0},{"id":"https://openalex.org/C162324750","wikidata":"https://www.wikidata.org/wiki/Q8134","display_name":"Economics","level":0,"score":0.0},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.0},{"id":"https://openalex.org/C120665830","wikidata":"https://www.wikidata.org/wiki/Q14620","display_name":"Optics","level":1,"score":0.0}],"mesh":[{"descriptor_ui":"D001580","descriptor_name":"Benzopyrenes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D001580","descriptor_name":"Benzopyrenes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D001580","descriptor_name":"Benzopyrenes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D001580","descriptor_name":"Benzopyrenes","qualifier_ui":"Q000633","qualifier_name":"toxicity","is_major_topic":false},{"descriptor_ui":"D001580","descriptor_name":"Benzopyrenes","qualifier_ui":"Q000633","qualifier_name":"toxicity","is_major_topic":false},{"descriptor_ui":"D001580","descriptor_name":"Benzopyrenes","qualifier_ui":"Q000633","qualifier_name":"toxicity","is_major_topic":false},{"descriptor_ui":"D002273","descriptor_name":"Carcinogens","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D002273","descriptor_name":"Carcinogens","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D002273","descriptor_name":"Carcinogens","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D002273","descriptor_name":"Carcinogens","qualifier_ui":"Q000633","qualifier_name":"toxicity","is_major_topic":false},{"descriptor_ui":"D002273","descriptor_name":"Carcinogens","qualifier_ui":"Q000633","qualifier_name":"toxicity","is_major_topic":false},{"descriptor_ui":"D002273","descriptor_name":"Carcinogens","qualifier_ui":"Q000633","qualifier_name":"toxicity","is_major_topic":false},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","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":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/jo0303822","doi":"https://doi.org/10.1021/jo0303822","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo0303822","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"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":"The Journal of Organic Chemistry","raw_type":"journal-article"},{"id":"pmid:15153038","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/15153038","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":"The Journal of organic chemistry","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"sustainable_development_goals_aurora":[{"id":"https://metadata.un.org/sdg/3","score":0.4699999988079071,"display_name":"Good health and well-being"}],"study_designs":[],"awards":[{"id":"https://openalex.org/G1491389018","display_name":null,"funder_award_id":"CA 17613","funder_id":"https://openalex.org/F4320337351","funder_display_name":"National Cancer Institute"},{"id":"https://openalex.org/G2906807265","display_name":null,"funder_award_id":"N02-CB-37025-48","funder_id":"https://openalex.org/F4320337351","funder_display_name":"National Cancer Institute"},{"id":"https://openalex.org/G7097651146","display_name":"CANCER CENTER SUPPORT GRANT","funder_award_id":"P30CA017613","funder_id":"https://openalex.org/F4320337351","funder_display_name":"National Cancer Institute"}],"funders":[{"id":"https://openalex.org/F4320337351","display_name":"National Cancer Institute","ror":"https://ror.org/040gcmg81"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":37,"referenced_works":["https://openalex.org/W99900191","https://openalex.org/W1646419439","https://openalex.org/W1982497326","https://openalex.org/W1989734490","https://openalex.org/W1990934241","https://openalex.org/W1994824322","https://openalex.org/W1995158158","https://openalex.org/W1996033279","https://openalex.org/W2017418899","https://openalex.org/W2019616514","https://openalex.org/W2020632399","https://openalex.org/W2022019415","https://openalex.org/W2022463820","https://openalex.org/W2027433468","https://openalex.org/W2027465882","https://openalex.org/W2031739237","https://openalex.org/W2054114446","https://openalex.org/W2054836547","https://openalex.org/W2056939737","https://openalex.org/W2062259508","https://openalex.org/W2074485558","https://openalex.org/W2076519777","https://openalex.org/W2077018913","https://openalex.org/W2078771835","https://openalex.org/W2085738604","https://openalex.org/W2116452745","https://openalex.org/W2146128502","https://openalex.org/W2155073279","https://openalex.org/W2396843460","https://openalex.org/W2949301891","https://openalex.org/W2949846816","https://openalex.org/W2950481467","https://openalex.org/W2950594197","https://openalex.org/W2952527478","https://openalex.org/W2952970280","https://openalex.org/W3005253218","https://openalex.org/W4235957001"],"related_works":["https://openalex.org/W1974061584","https://openalex.org/W1963863410","https://openalex.org/W2014080966","https://openalex.org/W1982497326","https://openalex.org/W2022463820","https://openalex.org/W2019616514","https://openalex.org/W3081529581","https://openalex.org/W2208559915","https://openalex.org/W2952827919","https://openalex.org/W2061330409"],"abstract_inverted_index":{"Dibenzo[def,p]chrysene":[0],"(DBC)":[1],"(1),":[2],"is":[3,23],"by":[4],"far":[5],"the":[6,27,48,63],"most":[7],"mutagenic":[8],"and":[9,38,53,67],"toxic":[10],"polycyclic":[11],"aromatic":[12],"hydrocarbon":[13],"identified.":[14],"Its":[15],"metabolic":[16],"activation":[17],"leads":[18],"to":[19,26,34],"trans-11,12-dihydroxy-11,12-dihydro-DBC":[20],"(2),":[21],"which":[22],"further":[24],"metabolized":[25],"ultimate":[28],"metabolite,":[29],"anti-trans-11,12-dihydroxy-13,14-epoxy-11,12,13,14-tetrahydro-DBC":[30],"(3),":[31],"that":[32],"binds":[33],"DNA":[35],"causing":[36],"mutations":[37],"ultimately":[39],"tumor":[40],"induction.":[41],"We":[42],"report":[43],"a":[44,59,70],"facile":[45],"route":[46],"for":[47,62],"syntheses":[49],"of":[50,65],"DBC":[51],"(1)":[52],"its":[54],"12-methoxy":[55],"derivative":[56],"(12-methoxy-DBC)":[57],"(13),":[58],"key":[60],"intermediate":[61],"synthesis":[64],"2":[66],"3,":[68],"using":[69],"Suzuki":[71],"cross-coupling":[72],"approach.":[73]},"counts_by_year":[{"year":2025,"cited_by_count":2},{"year":2024,"cited_by_count":1},{"year":2022,"cited_by_count":2},{"year":2021,"cited_by_count":2},{"year":2019,"cited_by_count":1},{"year":2018,"cited_by_count":1},{"year":2017,"cited_by_count":2},{"year":2016,"cited_by_count":1},{"year":2015,"cited_by_count":1},{"year":2014,"cited_by_count":2},{"year":2013,"cited_by_count":1},{"year":2012,"cited_by_count":1}],"updated_date":"2026-10-28T10:33:24.094632","created_date":"2016-06-24T00:00:00"}