{"id":"https://openalex.org/W2053424482","doi":"https://doi.org/10.1021/jm00146a016","title":"Synthesis of xanthines as adenosine antagonists, a practical quantitative structure-activity relationship application","display_name":"Synthesis of xanthines as adenosine antagonists, a practical quantitative structure-activity relationship application","publication_year":1985,"publication_date":"1985-08-01","ids":{"openalex":"https://openalex.org/W2053424482","doi":"https://doi.org/10.1021/jm00146a016","mag":"2053424482","pmid":"https://pubmed.ncbi.nlm.nih.gov/2991519"},"language":"en","primary_location":{"id":"doi:10.1021/jm00146a016","doi":"https://doi.org/10.1021/jm00146a016","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jm00146a016","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","is_traditional":true,"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/A5042392280","display_name":"Harriet W. Hamilton","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Harriet W. Hamilton","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5111725409","display_name":"Daniel F. Ortwine","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Daniel F. Ortwine","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5110487140","display_name":"Donald F. Worth","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Donald F. Worth","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5000235502","display_name":"Edward W. Badger","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Edward W. Badger","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5044610434","display_name":"James A. Bristol","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"James A. Bristol","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5090701680","display_name":"Robert F. Bruns","orcid":"https://orcid.org/0000-0001-7142-9881","observed_orcids":["https://orcid.org/0000-0001-7142-9881"]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Robert F. Bruns","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5111761044","display_name":"Stephen J. Haleen","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Stephen J. Haleen","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"last","author":{"id":"https://openalex.org/A5113505012","display_name":"Robert P. Steffen","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Robert P. Steffen","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":2.4831,"has_fulltext":false,"cited_by_count":60,"citation_normalized_percentile":{"value":0.89112051,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":95},"biblio":{"volume":"28","issue":"8","first_page":"1071","last_page":"1079"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11193","display_name":"Adenosine and Purinergic Signaling","score":0.7900000214576721,"subfield":{"id":"https://openalex.org/subfields/1314","display_name":"Physiology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},"topics":[{"id":"https://openalex.org/T11193","display_name":"Adenosine and Purinergic Signaling","score":0.7900000214576721,"subfield":{"id":"https://openalex.org/subfields/1314","display_name":"Physiology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T10211","display_name":"Computational Drug Discovery Methods","score":0.20200000703334808,"subfield":{"id":"https://openalex.org/subfields/3002","display_name":"Drug Discovery"},"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/T10274","display_name":"Heterocyclic Compound Synthesis and Bioactivity","score":0.0012000000569969416,"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/xanthine","display_name":"xanthine","score":0.8970000147819519},{"id":"https://openalex.org/keywords/adenosine-a1-receptor-antagonist","display_name":"adenosine A1 receptor antagonist","score":0.9089999794960022},{"id":"https://openalex.org/keywords/qsar","display_name":"QSAR","score":0.9089999794960022},{"id":"https://openalex.org/keywords/sulfonamide-derivatives","display_name":"sulfonamide derivatives","score":0.8600000143051147},{"id":"https://openalex.org/keywords/water-solubility","display_name":"water solubility","score":0.9470000267028809},{"id":"https://openalex.org/keywords/receptor-binding-potency","display_name":"receptor binding potency","score":0.7419999837875366},{"id":"https://openalex.org/keywords/adenosine-receptor-antagonism","display_name":"adenosine receptor antagonism","score":0.7350000143051147}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9502248167991638},{"id":"https://openalex.org/C2776991684","wikidata":"https://www.wikidata.org/wiki/Q190012","display_name":"Adenosine","level":2,"score":0.5568029880523682},{"id":"https://openalex.org/C98274493","wikidata":"https://www.wikidata.org/wiki/Q128406","display_name":"Pharmacology","level":1,"score":0.44721224904060364},{"id":"https://openalex.org/C193042331","wikidata":"https://www.wikidata.org/wiki/Q1772003","display_name":"Structure\u2013activity relationship","level":3,"score":0.43567007780075073},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.3628900647163391},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.28464260697364807},{"id":"https://openalex.org/C202751555","wikidata":"https://www.wikidata.org/wiki/Q221681","display_name":"In vitro","level":2,"score":0.16787096858024597},{"id":"https://openalex.org/C71924100","wikidata":"https://www.wikidata.org/wiki/Q11190","display_name":"Medicine","level":0,"score":0.0}],"mesh":[{"descriptor_ui":"D000241","descriptor_name":"Adenosine","qualifier_ui":"Q000037","qualifier_name":"antagonists & inhibitors","is_major_topic":true},{"descriptor_ui":"D000818","descriptor_name":"Animals","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D001921","descriptor_name":"Brain","qualifier_ui":"Q000187","qualifier_name":"drug effects","is_major_topic":false},{"descriptor_ui":"D002417","descriptor_name":"Cattle","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D006321","descriptor_name":"Heart","qualifier_ui":"Q000187","qualifier_name":"drug effects","is_major_topic":false},{"descriptor_ui":"D011956","descriptor_name":"Receptors, Cell Surface","qualifier_ui":"Q000187","qualifier_name":"drug effects","is_major_topic":false},{"descriptor_ui":"D011956","descriptor_name":"Receptors, Cell Surface","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D011983","descriptor_name":"Receptors, Purinergic","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":"D014970","descriptor_name":"Xanthines","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D014970","descriptor_name":"Xanthines","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D014970","descriptor_name":"Xanthines","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":true},{"descriptor_ui":"D051381","descriptor_name":"Rats","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D066298","descriptor_name":"In Vitro Techniques","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/jm00146a016","doi":"https://doi.org/10.1021/jm00146a016","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jm00146a016","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:2991519","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/2991519","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":"Comparative Study"}],"best_oa_location":null,"sustainable_development_goals":[{"display_name":"Good health and well-being","id":"https://metadata.un.org/sdg/3","score":0.4715999960899353}],"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/W2079439099","https://openalex.org/W2067504200","https://openalex.org/W2470536667","https://openalex.org/W1535167542","https://openalex.org/W1999654467","https://openalex.org/W2009492979","https://openalex.org/W1977763879","https://openalex.org/W2016775717","https://openalex.org/W2050627616","https://openalex.org/W1971472068"],"abstract_inverted_index":{"A":[0],"set":[1],"of":[2,45,47,75,118],"56":[3],"8-phenylxanthines,":[4],"previously":[5],"tested":[6],"for":[7],"adenosine":[8,120],"antagonism":[9,117],"(adenosine":[10],"A1":[11],"receptor":[12,31,121],"affinity),":[13],"was":[14,59,96,111,125],"analyzed":[15],"by":[16,64,105],"quantitative":[17],"structure-activity":[18],"relationship":[19],"(QSAR)":[20],"techniques.":[21],"The":[22],"resulting":[23,100],"QSAR":[24],"revealed":[25],"that":[26,84],"(1)":[27],"the":[28,43,73,99,106],"most":[29],"potent":[30],"binders":[32],"had":[33],"already":[34],"been":[35],"made":[36],"in":[37,66,115],"this":[38,76],"series":[39],"and":[40,56,108],"thus":[41],"suggested":[42],"termination":[44],"synthesis":[46],"compounds":[48,81],"with":[49],"additional":[50,79],"phenyl":[51,70],"substituents":[52,88],"to":[53,90],"increase":[54,91],"potency":[55,58,95],"(2)":[57],"much":[60],"more":[61],"strongly":[62],"affected":[63],"changes":[65],"ortho":[67],"than":[68],"para":[69,87],"substitution.":[71],"On":[72],"basis":[74],"study,":[77],"an":[78,119],"20":[80],"were":[82],"synthesized":[83],"contained":[85],"primarily":[86],"designed":[89],"aqueous":[92,109],"solubility.":[93],"High":[94],"maintained":[97],"among":[98],"sulfonamide":[101],"derivatives":[102],"(as":[103],"predicted":[104],"QSAR),":[107],"solubility":[110],"dramatically":[112],"increased.":[113],"Furthermore,":[114],"vitro":[116],"mediated":[122],"physiological":[123],"effect":[124],"demonstrated.":[126]},"counts_by_year":[{"year":2022,"cited_by_count":1},{"year":2021,"cited_by_count":2},{"year":2019,"cited_by_count":1},{"year":2016,"cited_by_count":1},{"year":2012,"cited_by_count":1}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}
