{"id":"https://openalex.org/W2045448654","doi":"https://doi.org/10.1021/jm020339r","title":"Synthesis and Antiviral Activity of Novel Erythrofuranosyl Imidazo[1,2-a]pyridine C-Nucleosides Constructed via Palladium Coupling of Iodoimidazo[1,2-a]pyridines and Dihydrofuran","display_name":"Synthesis and Antiviral Activity of Novel Erythrofuranosyl Imidazo[1,2-a]pyridine C-Nucleosides Constructed via Palladium Coupling of Iodoimidazo[1,2-a]pyridines and Dihydrofuran","publication_year":2003,"publication_date":"2003-03-07","ids":{"openalex":"https://openalex.org/W2045448654","doi":"https://doi.org/10.1021/jm020339r","mag":"2045448654","pmid":"https://pubmed.ncbi.nlm.nih.gov/12672244"},"language":"en","primary_location":{"id":"doi:10.1021/jm020339r","doi":"https://doi.org/10.1021/jm020339r","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jm020339r","pdf_url":null,"source":{"id":"https://openalex.org/S162030435","display_name":"Journal of Medicinal Chemistry","issn_l":"0022-2623","issn":["0022-2623","1520-4804"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-a","jufo-3","ki-jl-2","medline","norway-2","poland-200","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":"Journal of Medicinal 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/A5054596609","display_name":"Kristjan S. Gudmundsson","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I27837315","display_name":"University of Michigan","ror":"https://ror.org/00jmfr291","country_code":"US","type":"education","lineage":["https://openalex.org/I27837315"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Kristjan S. Gudmundsson","raw_affiliation_strings":["Department of Medicinal Chemistry, College of Pharmacy; Department of Chemistry, College of Literature, Sciences and the Arts; and Department of Biologic and Materials Sciences, School of Dentistry; The University of Michigan, Ann Arbor, Michigan 48019-1065"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Medicinal Chemistry, College of Pharmacy; Department of Chemistry, College of Literature, Sciences and the Arts; and Department of Biologic and Materials Sciences, School of Dentistry; The University of Michigan, Ann Arbor, Michigan 48019-1065","institution_ids":["https://openalex.org/I27837315"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5018266807","display_name":"John David Williams","orcid":"https://orcid.org/0000-0001-6609-3842","observed_orcids":["https://orcid.org/0000-0001-6609-3842"]},"institutions":[{"id":"https://openalex.org/I27837315","display_name":"University of Michigan","ror":"https://ror.org/00jmfr291","country_code":"US","type":"education","lineage":["https://openalex.org/I27837315"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"John D. Williams","raw_affiliation_strings":["Department of Medicinal Chemistry, College of Pharmacy; Department of Chemistry, College of Literature, Sciences and the Arts; and Department of Biologic and Materials Sciences, School of Dentistry; The University of Michigan, Ann Arbor, Michigan 48019-1065"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Medicinal Chemistry, College of Pharmacy; Department of Chemistry, College of Literature, Sciences and the Arts; and Department of Biologic and Materials Sciences, School of Dentistry; The University of Michigan, Ann Arbor, Michigan 48019-1065","institution_ids":["https://openalex.org/I27837315"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5110073621","display_name":"John C. Drach","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I27837315","display_name":"University of Michigan","ror":"https://ror.org/00jmfr291","country_code":"US","type":"education","lineage":["https://openalex.org/I27837315"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"John C. Drach","raw_affiliation_strings":["Department of Medicinal Chemistry, College of Pharmacy; Department of Chemistry, College of Literature, Sciences and the Arts; and Department of Biologic and Materials Sciences, School of Dentistry; The University of Michigan, Ann Arbor, Michigan 48019-1065"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Medicinal Chemistry, College of Pharmacy; Department of Chemistry, College of Literature, Sciences and the Arts; and Department of Biologic and Materials Sciences, School of Dentistry; The University of Michigan, Ann Arbor, Michigan 48019-1065","institution_ids":["https://openalex.org/I27837315"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5103853042","display_name":"Leroy B. Townsend","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I27837315","display_name":"University of Michigan","ror":"https://ror.org/00jmfr291","country_code":"US","type":"education","lineage":["https://openalex.org/I27837315"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Leroy B. Townsend","raw_affiliation_strings":["Department of Medicinal Chemistry, College of Pharmacy; Department of Chemistry, College of Literature, Sciences and the Arts; and Department of Biologic and Materials Sciences, School of Dentistry; The University of Michigan, Ann Arbor, Michigan 48019-1065"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Medicinal Chemistry, College of Pharmacy; Department of Chemistry, College of Literature, Sciences and the Arts; and Department of Biologic and Materials Sciences, School of Dentistry; The University of Michigan, Ann Arbor, Michigan 48019-1065","institution_ids":["https://openalex.org/I27837315"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I27837315"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":1.5772,"has_fulltext":false,"cited_by_count":134,"citation_normalized_percentile":{"value":0.79223301,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":99},"biblio":{"volume":"46","issue":"8","first_page":"1449","last_page":"1455"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10835","display_name":"Carbohydrate Chemistry and Synthesis","score":0.6714000105857849,"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/T10835","display_name":"Carbohydrate Chemistry and Synthesis","score":0.6714000105857849,"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":0.08309999853372574,"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/T10526","display_name":"HIV/AIDS drug development and treatment","score":0.052299998700618744,"subfield":{"id":"https://openalex.org/subfields/2725","display_name":"Infectious Diseases"},"field":{"id":"https://openalex.org/fields/27","display_name":"Medicine"},"domain":{"id":"https://openalex.org/domains/4","display_name":"Health Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/palladium-catalyzed-coupling","display_name":"palladium-catalyzed coupling","score":0.7549999952316284},{"id":"https://openalex.org/keywords/2-3-dihydrofuran","display_name":"2,3-dihydrofuran","score":0.8830000162124634},{"id":"https://openalex.org/keywords/human-cytomegalovirus","display_name":"human cytomegalovirus","score":0.8960000276565552},{"id":"https://openalex.org/keywords/herpes-simplex-virus-type-1","display_name":"herpes simplex virus type 1","score":0.8989999890327454},{"id":"https://openalex.org/keywords/antiviral-activity","display_name":"antiviral activity","score":0.8270000219345093},{"id":"https://openalex.org/keywords/diastereoselective-synthesis","display_name":"diastereoselective synthesis","score":0.734000027179718},{"id":"https://openalex.org/keywords/chiral-chromatography","display_name":"chiral chromatography","score":0.7250000238418579}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9565652012825012},{"id":"https://openalex.org/C2779485729","wikidata":"https://www.wikidata.org/wiki/Q210385","display_name":"Pyridine","level":2,"score":0.8664259910583496},{"id":"https://openalex.org/C7947691","wikidata":"https://www.wikidata.org/wiki/Q567575","display_name":"Anomer","level":2,"score":0.6297121047973633},{"id":"https://openalex.org/C2779424567","wikidata":"https://www.wikidata.org/wiki/Q422021","display_name":"Osmium tetroxide","level":3,"score":0.6205753684043884},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5820635557174683},{"id":"https://openalex.org/C502130503","wikidata":"https://www.wikidata.org/wiki/Q1089","display_name":"Palladium","level":3,"score":0.5195170640945435},{"id":"https://openalex.org/C2777672777","wikidata":"https://www.wikidata.org/wiki/Q19903952","display_name":"Dihydroxylation","level":4,"score":0.4952222406864166},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.4161240756511688},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.21762141585350037},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.12089717388153076},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.11476010084152222},{"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},{"id":"https://openalex.org/C93877712","wikidata":"https://www.wikidata.org/wiki/Q132560","display_name":"Electron microscope","level":2,"score":0.0}],"mesh":[{"descriptor_ui":"D000998","descriptor_name":"Antiviral Agents","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D000998","descriptor_name":"Antiviral Agents","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":false},{"descriptor_ui":"D000998","descriptor_name":"Antiviral Agents","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D002384","descriptor_name":"Catalysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D002460","descriptor_name":"Cell Line","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D003587","descriptor_name":"Cytomegalovirus","qualifier_ui":"Q000187","qualifier_name":"drug effects","is_major_topic":false},{"descriptor_ui":"D004797","descriptor_name":"Enzyme-Linked Immunosorbent Assay","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D005663","descriptor_name":"Furans","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D006801","descriptor_name":"Humans","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D009705","descriptor_name":"Nucleosides","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D009705","descriptor_name":"Nucleosides","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":false},{"descriptor_ui":"D009705","descriptor_name":"Nucleosides","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D010165","descriptor_name":"Palladium","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D010948","descriptor_name":"Viral Plaque Assay","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D011725","descriptor_name":"Pyridines","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D011725","descriptor_name":"Pyridines","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":false},{"descriptor_ui":"D011725","descriptor_name":"Pyridines","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D013237","descriptor_name":"Stereoisomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013329","descriptor_name":"Structure-Activity Relationship","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D018259","descriptor_name":"Herpesvirus 1, Human","qualifier_ui":"Q000187","qualifier_name":"drug effects","is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/jm020339r","doi":"https://doi.org/10.1021/jm020339r","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jm020339r","pdf_url":null,"source":{"id":"https://openalex.org/S162030435","display_name":"Journal of Medicinal Chemistry","issn_l":"0022-2623","issn":["0022-2623","1520-4804"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-a","jufo-3","ki-jl-2","medline","norway-2","poland-200","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":"Journal of Medicinal Chemistry","raw_type":"journal-article"},{"id":"pmid:12672244","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/12672244","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 medicinal chemistry","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[{"id":"https://metadata.un.org/sdg/3","score":0.5683000087738037,"display_name":"Good health and well-being"}],"study_designs":[],"awards":[{"id":"https://openalex.org/G3768207773","display_name":"NEW CHEMICAL ENTITIES AND UNIQUE TARGETS FOR HCMV","funder_award_id":"P01AI046390","funder_id":"https://openalex.org/F4320337355","funder_display_name":"National Institute of Allergy and Infectious Diseases"},{"id":"https://openalex.org/G4079792059","display_name":"Interdepartmental Training in Pharmacological Sciences","funder_award_id":"T32GM007767","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"},{"id":"https://openalex.org/G8722106665","display_name":"NEW INHIBITORS AND NEW TARGETS TO DEVELOP HCMV DRUGS","funder_award_id":"U19AI031718","funder_id":"https://openalex.org/F4320337355","funder_display_name":"National Institute of Allergy and Infectious Diseases"}],"funders":[{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"},{"id":"https://openalex.org/F4320337355","display_name":"National Institute of Allergy and Infectious Diseases","ror":"https://ror.org/043z4tv69"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":23,"referenced_works":["https://openalex.org/W35926420","https://openalex.org/W115238100","https://openalex.org/W1508311454","https://openalex.org/W1775434210","https://openalex.org/W1926456818","https://openalex.org/W1965204002","https://openalex.org/W1972770998","https://openalex.org/W1993425396","https://openalex.org/W2018879164","https://openalex.org/W2063301167","https://openalex.org/W2080445222","https://openalex.org/W2080573779","https://openalex.org/W2081188967","https://openalex.org/W2090723716","https://openalex.org/W2098931536","https://openalex.org/W2165260654","https://openalex.org/W2949160335","https://openalex.org/W2950125885","https://openalex.org/W2951385707","https://openalex.org/W2952602650","https://openalex.org/W2953322759","https://openalex.org/W4235752277","https://openalex.org/W4242927370"],"related_works":["https://openalex.org/W2626404586","https://openalex.org/W1973765947","https://openalex.org/W2180307180","https://openalex.org/W1999115221","https://openalex.org/W2074702348","https://openalex.org/W4302041402","https://openalex.org/W2950580667","https://openalex.org/W2760961771","https://openalex.org/W2086726544","https://openalex.org/W2005244982"],"abstract_inverted_index":{"2,5,6-Trichloro-1-(beta-d-ribofuranosyl)benzimidazole":[0],"(TCRB)":[1],"and":[2,52,60,85,93],"certain":[3],"analogues":[4],"have":[5],"shown":[6],"significant":[7],"activity":[8],"against":[9],"human":[10],"cytomegalovirus.":[11],"The":[12],"metabolic":[13],"instability":[14],"of":[15,37,58,63,77,99,108],"the":[16,25,35,96,104,109,112],"glycosidic":[17],"linkage":[18],"in":[19],"TCRB":[20],"prompted":[21],"us":[22],"to":[23,34,54,102,116],"synthesize":[24],"structurally":[26],"similar":[27],"imidazo[1,2-a]pyridine":[28,39],"erythrofuranosyl":[29,78],"C-nucleosides.":[30],"As":[31],"an":[32],"approach":[33],"synthesis":[36],"polychlorinated":[38],"C-3-erythrofuranosides,":[40],"a":[41,75],"palladium-based":[42],"methodology":[43],"for":[44,91],"coupling":[45],"2,3-dihydrofuran":[46],"with":[47,67,71],"chlorinated":[48],"3-iodoimidazo[1,2-a]pyridines":[49],"was":[50],"developed":[51],"optimized":[53],"give":[55],"80-90%":[56],"yields":[57],"2,6-dichloro-":[59],"2,6,7-trichloro-3-(2,3-dideoxy-2,3-didehydro-d/l-erythrofuranosyl)imidazo[1,2-a]pyridine.":[61],"Dihydroxylation":[62],"these":[64],"didehydro":[65],"derivatives":[66],"osmium":[68],"tetroxide":[69],"or":[70],"AD-mix":[72],"alpha":[73],"gave":[74],"mixture":[76],"C-nucleosides":[79],"that":[80],"were":[81],"separated":[82],"by":[83],"standard":[84],"then":[86],"chiral":[87],"chromatography.":[88],"When":[89],"screened":[90],"anti-HCMV":[92],"HSV-1":[94],"activity,":[95],"alpha-d":[97],"anomer":[98],"2,6,7-trichloro-3-(erythrofuranosyl)imidazo[1,2-a]pyridine":[100],"proved":[101,115],"be":[103,117],"most":[105],"active":[106],"member":[107],"series,":[110],"while":[111],"beta-anomers":[113],"all":[114],"inactive.":[118]},"counts_by_year":[{"year":2026,"cited_by_count":4},{"year":2025,"cited_by_count":2},{"year":2024,"cited_by_count":7},{"year":2023,"cited_by_count":10},{"year":2022,"cited_by_count":7},{"year":2021,"cited_by_count":6},{"year":2020,"cited_by_count":11},{"year":2019,"cited_by_count":11},{"year":2018,"cited_by_count":7},{"year":2017,"cited_by_count":8},{"year":2016,"cited_by_count":8},{"year":2015,"cited_by_count":8},{"year":2014,"cited_by_count":9},{"year":2013,"cited_by_count":1},{"year":2012,"cited_by_count":5}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}