{"doi":"10.1002/chem.202100032","title":"A Concise Total Synthesis of Dehydroantofine and Its Antimalarial Activity against Chloroquine‐Resistant <i>Plasmodium falciparum</i>","abstract":"<jats:title>Abstract</jats:title><jats:p>The total synthesis of dehydroantofine was achieved by employing a novel, regioselective, azahetero Diels–Alder reaction of easily accessible 3,5‐dichloro‐2<jats:italic>H</jats:italic>‐1,4‐oxazin‐2‐one with <jats:bold>14 a</jats:bold> as a key step. Furthermore, it is demonstrated that dehydroantofine is a promising candidate as a new antimalarial agent in a biological assay with chloroquine‐resistant <jats:italic>Plasmodium falciparum</jats:italic>.</jats:p>","journal":"Chemistry – A European Journal","year":2021,"id":659504,"datarank":0.24141568686511508,"base_score":1.6094379124341003,"endowment":1.6094379124341003,"self_citation_contribution":0.24141568686511508,"citation_network_contribution":0.0,"self_endowment_contribution":0.24141568686511508,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":4,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":5,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1721594,"name":"Ikumi Iwasaki","orcid":null,"position":1,"is_corresponding":false},{"id":1721596,"name":"Kazu Sakumi","orcid":null,"position":2,"is_corresponding":false},{"id":1721598,"name":"Rei Hokari","orcid":"0000-0002-6091-0503","position":3,"is_corresponding":false},{"id":1721600,"name":"Aki Ishiyama","orcid":"0000-0003-4703-8834","position":4,"is_corresponding":false},{"id":1721602,"name":"Masato Iwatsuki","orcid":"0000-0001-8373-4314","position":5,"is_corresponding":false},{"id":1721605,"name":"Masataka Nakahara","orcid":null,"position":6,"is_corresponding":false},{"id":1721608,"name":"Shuhei Higashibayashi","orcid":"0000-0002-2957-461X","position":7,"is_corresponding":false},{"id":1721610,"name":"Takeshi Sugai","orcid":"0000-0003-4416-6435","position":8,"is_corresponding":false},{"id":1721612,"name":"Hiroshi Imagawa","orcid":"0000-0003-0708-713X","position":9,"is_corresponding":false},{"id":1721613,"name":"Miwa Kubo","orcid":"0000-0002-7271-3128","position":10,"is_corresponding":false},{"id":1721615,"name":"Yoshiyasu Fukuyama","orcid":"0000-0003-0989-172X","position":11,"is_corresponding":false},{"id":1721617,"name":"Satoshi Ōmura","orcid":null,"position":12,"is_corresponding":false},{"id":148775,"name":"Hirofumi Yamamoto","orcid":"0000-0001-7788-2580","position":13,"is_corresponding":false},{"id":1107779,"name":"Naoto Yamasaki","orcid":"0000-0002-2105-7968","position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"resolved":true,"title":"A Concise Total Synthesis of Dehydroantofine and Its Antimalarial Activity against Chloroquine‐Resistant <i>Plasmodium falciparum</i>","abstract":"<jats:title>Abstract</jats:title><jats:p>The total synthesis of dehydroantofine was achieved by employing a novel, regioselective, azahetero Diels–Alder reaction of easily accessible 3,5‐dichloro‐2<jats:italic>H</jats:italic>‐1,4‐oxazin‐2‐one with <jats:bold>14 a</jats:bold> as a key step. Furthermore, it is demonstrated that dehydroantofine is a promising candidate as a new antimalarial agent in a biological assay with chloroquine‐resistant <jats:italic>Plasmodium falciparum</jats:italic>.</jats:p>","is_dataset_classified":null,"base_score":1.6094379124341003,"endowment":1.6094379124341003,"datacite_reuse_total":5,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"33482050","pmcid":null,"openalex_id":"https://openalex.org/W3122434724","authors":[],"funders":[{"funder_name":"MEXT (Ministry of Education, Culture, Sports, Science, and Technology) of the Japanese Government.","grant_id":"18K05365","title":null}],"total_grants":1,"fwci":0.6993,"citation_percentile":0.68549304,"influential_citations":0,"citation_trend":[{"year":2021,"count":1},{"year":2023,"count":1},{"year":2024,"count":2}],"oa_status":"closed","license":"http://onlinelibrary.wiley.com/termsAndConditions#vor","oa_locations":[{"url":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.202100032","host_type":"publisher"},{"url":"https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chem.202100032","host_type":"publisher"},{"url":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/chem.202100032","host_type":"publisher"},{"url":"https://doi.org/10.1002/chem.202100032","host_type":"journal"},{"url":"https://pubmed.ncbi.nlm.nih.gov/33482050","host_type":"repository"}],"fields_of_study":["Alkaloids: synthesis and pharmacology","Traditional and Medicinal Uses of Annonaceae","Chemical synthesis and alkaloids","Medicine","Chemistry","Antimalarials","Chloroquine","Drug Resistance","Plasmodium falciparum"],"mesh_terms":["Antimalarials","Chloroquine","Drug Resistance","Plasmodium falciparum"],"keywords":["Plasmodium falciparum","Chloroquine","Regioselectivity","Antimalarial Agent","Chemistry","Stereochemistry","Plasmodium (life cycle)","Combinatorial chemistry","Malaria","Biology","Biochemistry","Parasite hosting","Computer science","Immunology","Catalysis","Antimalarial Drugs","Density Functional Calculations","Diels-alder Reactions","Pi Interactions","Dehydroantofine"],"sdg_mappings":[],"linked_datasets":[{"doi":"10.5517/ccdc.csd.cc25j4f9","title":"CCDC 2011510: Experimental Crystal Structure Determination","publisher":"Cambridge Crystallographic Data Centre","resource_type":"Dataset"},{"doi":"10.5517/ccdc.csd.cc25j4d8","title":"CCDC 2011509: Experimental Crystal Structure Determination","publisher":"Cambridge Crystallographic Data Centre","resource_type":"Dataset"},{"doi":"10.5517/ccdc.csd.cc25hyxk","title":"CCDC 2011339: Experimental Crystal Structure Determination","publisher":"Cambridge Crystallographic Data Centre","resource_type":"Dataset"},{"doi":"10.5517/ccdc.csd.cc25hywj","title":"CCDC 2011338: Experimental Crystal Structure Determination","publisher":"Cambridge Crystallographic Data Centre","resource_type":"Dataset"},{"doi":"10.5517/ccdc.csd.cc25hyvh","title":"CCDC 2011337: Experimental Crystal Structure Determination","publisher":"Cambridge Crystallographic Data Centre","resource_type":"Dataset"}],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-08-12T07:03:07.374208Z","pmid":null,"pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}