{"id":"https://openalex.org/W2035982103","doi":"https://doi.org/10.1021/jm950835y","title":"Synthesis of Non-nucleoside Analogs of Toyocamycin, Sangivamycin, and Thiosangivamycin: The Effect of Certain 4- and 4,6-Substituents on the Antiviral Activity of Pyrrolo[2,3-d]pyrimidines","display_name":"Synthesis of Non-nucleoside Analogs of Toyocamycin, Sangivamycin, and Thiosangivamycin: The Effect of Certain 4- and 4,6-Substituents on the Antiviral Activity of Pyrrolo[2,3-d]pyrimidines","publication_year":1996,"publication_date":"1996-01-01","ids":{"openalex":"https://openalex.org/W2035982103","doi":"https://doi.org/10.1021/jm950835y","mag":"2035982103","pmid":"https://pubmed.ncbi.nlm.nih.gov/8784444"},"language":"en","primary_location":{"id":"doi:10.1021/jm950835y","doi":"https://doi.org/10.1021/jm950835y","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jm950835y","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/A5083356428","display_name":"Thomas E. Renau","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":"Thomas E. Renau","raw_affiliation_strings":["Department of Medicinal Chemistry, College of Pharmacy, Department of Chemistry, College of Literature Sciences and Arts, and Department of Biologic and Materials Sciences, School of Dentistry, The University of Michigan, Ann Arbor, Michigan 48109-1065"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Medicinal Chemistry, College of Pharmacy, Department of Chemistry, College of Literature Sciences and Arts, and Department of Biologic and Materials Sciences, School of Dentistry, The University of Michigan, Ann Arbor, Michigan 48109-1065","institution_ids":["https://openalex.org/I27837315"]}]},{"author_position":"middle","author":{"id":null,"display_name":"Christopher Kennedy","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":"Christopher Kennedy","raw_affiliation_strings":["Department of Medicinal Chemistry, College of Pharmacy, Department of Chemistry, College of Literature Sciences and Arts, and Department of Biologic and Materials Sciences, School of Dentistry, The University of Michigan, Ann Arbor, Michigan 48109-1065"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Medicinal Chemistry, College of Pharmacy, Department of Chemistry, College of Literature Sciences and Arts, and Department of Biologic and Materials Sciences, School of Dentistry, The University of Michigan, Ann Arbor, Michigan 48109-1065","institution_ids":["https://openalex.org/I27837315"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5004932382","display_name":"Roger G. Ptak","orcid":"https://orcid.org/0000-0002-8492-3085","observed_orcids":["https://orcid.org/0000-0002-8492-3085"]},"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":"Roger G. Ptak","raw_affiliation_strings":["Department of Medicinal Chemistry, College of Pharmacy, Department of Chemistry, College of Literature Sciences and Arts, and Department of Biologic and Materials Sciences, School of Dentistry, The University of Michigan, Ann Arbor, Michigan 48109-1065"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Medicinal Chemistry, College of Pharmacy, Department of Chemistry, College of Literature Sciences and Arts, and Department of Biologic and Materials Sciences, School of Dentistry, The University of Michigan, Ann Arbor, Michigan 48109-1065","institution_ids":["https://openalex.org/I27837315"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5076281231","display_name":"Julie M. Breitenbach","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":"Julie M. Breitenbach","raw_affiliation_strings":["Department of Medicinal Chemistry, College of Pharmacy, Department of Chemistry, College of Literature Sciences and Arts, and Department of Biologic and Materials Sciences, School of Dentistry, The University of Michigan, Ann Arbor, Michigan 48109-1065"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Medicinal Chemistry, College of Pharmacy, Department of Chemistry, College of Literature Sciences and Arts, and Department of Biologic and Materials Sciences, School of Dentistry, The University of Michigan, Ann Arbor, Michigan 48109-1065","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 Arts, and Department of Biologic and Materials Sciences, School of Dentistry, The University of Michigan, Ann Arbor, Michigan 48109-1065"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Medicinal Chemistry, College of Pharmacy, Department of Chemistry, College of Literature Sciences and Arts, and Department of Biologic and Materials Sciences, School of Dentistry, The University of Michigan, Ann Arbor, Michigan 48109-1065","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 Arts, and Department of Biologic and Materials Sciences, School of Dentistry, The University of Michigan, Ann Arbor, Michigan 48109-1065"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Medicinal Chemistry, College of Pharmacy, Department of Chemistry, College of Literature Sciences and Arts, and Department of Biologic and Materials Sciences, School of Dentistry, The University of Michigan, Ann Arbor, Michigan 48109-1065","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":0.8626,"has_fulltext":false,"cited_by_count":35,"citation_normalized_percentile":{"value":0.66446668,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":99},"biblio":{"volume":"39","issue":"18","first_page":"3470","last_page":"3476"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T14099","display_name":"Synthesis and Characterization of Heterocyclic Compounds","score":0.5830000042915344,"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/T14099","display_name":"Synthesis and Characterization of Heterocyclic Compounds","score":0.5830000042915344,"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":0.18979999423027039,"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"}},{"id":"https://openalex.org/T10625","display_name":"Herpesvirus Infections and Treatments","score":0.05730000138282776,"subfield":{"id":"https://openalex.org/subfields/2713","display_name":"Epidemiology"},"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/pyrrolo-2-3-d-pyrimidine","display_name":"pyrrolo[2,3-d]pyrimidine","score":0.9449999928474426},{"id":"https://openalex.org/keywords/toyocamycin","display_name":"toyocamycin","score":0.9399999976158142},{"id":"https://openalex.org/keywords/sangivamycin","display_name":"sangivamycin","score":1.0},{"id":"https://openalex.org/keywords/nucleoside-antibiotics","display_name":"nucleoside antibiotics","score":0.9470000267028809},{"id":"https://openalex.org/keywords/antiviral-activity","display_name":"antiviral activity","score":0.8429999947547913},{"id":"https://openalex.org/keywords/human-cytomegalovirus","display_name":"human cytomegalovirus","score":0.9929999709129333},{"id":"https://openalex.org/keywords/herpes-simplex-virus-type-1","display_name":"herpes simplex virus type 1","score":0.996999979019165},{"id":"https://openalex.org/keywords/structure-activity-relationship","display_name":"structure-activity relationship","score":0.7120000123977661}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8991023302078247},{"id":"https://openalex.org/C2777650178","wikidata":"https://www.wikidata.org/wiki/Q419481","display_name":"Thioamide","level":2,"score":0.8831533193588257},{"id":"https://openalex.org/C2779321679","wikidata":"https://www.wikidata.org/wiki/Q207722","display_name":"Pyrimidine","level":2,"score":0.7267411947250366},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.6952649354934692},{"id":"https://openalex.org/C2776543447","wikidata":"https://www.wikidata.org/wiki/Q28734","display_name":"Nucleoside","level":2,"score":0.6907353401184082},{"id":"https://openalex.org/C2779240715","wikidata":"https://www.wikidata.org/wiki/Q333936","display_name":"Nitrile","level":2,"score":0.6653839945793152},{"id":"https://openalex.org/C116073593","wikidata":"https://www.wikidata.org/wiki/Q864491","display_name":"Biological activity","level":3,"score":0.5618481040000916},{"id":"https://openalex.org/C2779820661","wikidata":"https://www.wikidata.org/wiki/Q6929","display_name":"Human cytomegalovirus","level":3,"score":0.5188461542129517},{"id":"https://openalex.org/C202751555","wikidata":"https://www.wikidata.org/wiki/Q221681","display_name":"In vitro","level":2,"score":0.5156213641166687},{"id":"https://openalex.org/C193042331","wikidata":"https://www.wikidata.org/wiki/Q1772003","display_name":"Structure\u2013activity relationship","level":3,"score":0.4948257803916931},{"id":"https://openalex.org/C40479148","wikidata":"https://www.wikidata.org/wiki/Q844460","display_name":"Syncytium","level":3,"score":0.4476001262664795},{"id":"https://openalex.org/C2776568683","wikidata":"https://www.wikidata.org/wiki/Q23005640","display_name":"Moiety","level":2,"score":0.44225984811782837},{"id":"https://openalex.org/C114373084","wikidata":"https://www.wikidata.org/wiki/Q273499","display_name":"Chemical synthesis","level":3,"score":0.42206865549087524},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.26386940479278564},{"id":"https://openalex.org/C1491633281","wikidata":"https://www.wikidata.org/wiki/Q7868","display_name":"Cell","level":2,"score":0.09408783912658691},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.061834245920181274},{"id":"https://openalex.org/C104317684","wikidata":"https://www.wikidata.org/wiki/Q7187","display_name":"Gene","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":"D003587","descriptor_name":"Cytomegalovirus","qualifier_ui":"Q000187","qualifier_name":"drug effects","is_major_topic":false},{"descriptor_ui":"D006801","descriptor_name":"Humans","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D011741","descriptor_name":"Pyrimidine Nucleosides","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D011743","descriptor_name":"Pyrimidines","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D011743","descriptor_name":"Pyrimidines","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":false},{"descriptor_ui":"D013329","descriptor_name":"Structure-Activity Relationship","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013872","descriptor_name":"Thionucleosides","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D014127","descriptor_name":"Toyocamycin","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"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/jm950835y","doi":"https://doi.org/10.1021/jm950835y","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jm950835y","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:8784444","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/8784444","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":[{"display_name":"Good health and well-being","id":"https://metadata.un.org/sdg/3","score":0.6240000128746033}],"study_designs":[],"awards":[{"id":"https://openalex.org/G3608580336","display_name":null,"funder_award_id":"N01 AI72641","funder_id":"https://openalex.org/F4320337355","funder_display_name":"National Institute of Allergy and Infectious Diseases"},{"id":"https://openalex.org/G4273480390","display_name":"DRUGS TO TREAT HUMAN CYTOMEGALOVIRUS INFECTIONS","funder_award_id":"n01ai072641-011","funder_id":"https://openalex.org/F4320332161","funder_display_name":"National Institutes of Health"},{"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/F4320306095","display_name":"American Cancer Society","ror":"https://ror.org/02e463172"},{"id":"https://openalex.org/F4320332161","display_name":"National Institutes of Health","ror":"https://ror.org/01cwqze88"},{"id":"https://openalex.org/F4320337355","display_name":"National Institute of Allergy and Infectious Diseases","ror":"https://ror.org/043z4tv69"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":10,"referenced_works":["https://openalex.org/W1972770998","https://openalex.org/W1998521798","https://openalex.org/W2005846310","https://openalex.org/W2008814850","https://openalex.org/W2045851692","https://openalex.org/W2090885086","https://openalex.org/W2124641346","https://openalex.org/W2135313031","https://openalex.org/W2165260654","https://openalex.org/W2317819115"],"related_works":["https://openalex.org/W2949878569","https://openalex.org/W2728524540","https://openalex.org/W2005846310","https://openalex.org/W2951537536","https://openalex.org/W2951562119","https://openalex.org/W2950918273","https://openalex.org/W2055058484","https://openalex.org/W2031478700","https://openalex.org/W2013886702","https://openalex.org/W1980993892"],"abstract_inverted_index":{"A":[0],"number":[1],"of":[2,70,76,91,153],"4-substituted":[3,88],"7-(ethoxymethyl)-":[4],"and":[5,7,10,15,24,28,36,55,95,112,128,147],"7-[(2-methoxyethoxy)methyl]pyrrolo[2,3-d]-pyrimidine-5-carbonitrile":[6],"-5-thiocarboxamide":[8,16],"derivatives":[9],"several":[11],"7-substituted":[12,155],"4,6-diaminopyrrolo[2,3-d]pyrimidine-5-carbonitrile,":[13],"-5-carboxamide,":[14],"analogs":[17,98,115],"related":[18],"to":[19,86],"the":[20,46,71,74,87,92,96,104],"nucleoside":[21],"antibiotics":[22],"toyocamycin":[23],"sangivamycin":[25],"were":[26,48,99,106,116],"prepared":[27],"tested":[29],"for":[30,134,159,176],"activity":[31,61,160,177],"against":[32,62,101,118,161,178],"human":[33],"cytomegalovirus":[34],"(HCMV)":[35],"herpes":[37],"simplex":[38],"virus":[39],"type":[40],"1":[41],"(HSV-1).":[42],"Biologically,":[43],"modifications":[44],"at":[45,125,145,151,174],"4-position":[47],"not":[49,168],"well":[50],"tolerated":[51],"in":[52,56,81],"cell":[53],"culture,":[54],"almost":[57],"all":[58,90],"cases":[59],"no":[60],"HCMV":[63],"or":[64],"HSV-1":[65],"was":[66],"observed.":[67],"Furthermore,":[68],"none":[69],"compounds":[72],"inhibited":[73],"growth":[75],"L1210":[77],"murine":[78],"leukemic":[79],"cells":[80],"vitro.":[82],"In":[83],"sharp":[84],"contrast":[85],"compounds,":[89],"4,6-diamino":[93,165],"5-nitrile":[94,114],"5-thioamide":[97],"active":[100],"HCMV,":[102,119,162],"whereas":[103,163],"5-carboxamides":[105],"inactive.":[107],"The":[108],"corresponding":[109],"4-amino":[110],"6-methylamino":[111],"6-dimethylamino":[113],"inactive":[117],"establishing":[120],"that":[121,141],"an":[122,142],"amino":[123,143],"group":[124,144,173],"both":[126],"C-4":[127,146],"C-6":[129],"is":[130],"a":[131,148,154,164,171],"likely":[132],"requirement":[133],"antiviral":[135],"activity.":[136],"Overall,":[137],"our":[138],"results":[139],"demonstrate":[140],"thioamide":[149,172],"moiety":[150],"C-5":[152,175],"pyrrolo[2,3-d]pyrimidine":[156],"are":[157],"essential":[158],"analog":[166],"does":[167],"necessarily":[169],"require":[170],"HCMV.":[179]},"counts_by_year":[{"year":2024,"cited_by_count":1},{"year":2020,"cited_by_count":2},{"year":2018,"cited_by_count":1},{"year":2017,"cited_by_count":1},{"year":2016,"cited_by_count":1},{"year":2015,"cited_by_count":1},{"year":2014,"cited_by_count":5},{"year":2013,"cited_by_count":2},{"year":2012,"cited_by_count":7}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}