{"id":"https://openalex.org/W2951214728","doi":"https://doi.org/10.1002/jhet.5570380132","title":"Conformationally restricted tricyclic analogues of lipophilic pyrido[2,3\u2010d]pyrimidine antifolates","display_name":"Conformationally restricted tricyclic analogues of lipophilic pyrido[2,3\u2010d]pyrimidine antifolates","publication_year":2001,"publication_date":"2001-01-01","ids":{"openalex":"https://openalex.org/W2951214728","doi":"https://doi.org/10.1002/jhet.5570380132","mag":"2951214728"},"language":"en","primary_location":{"id":"doi:10.1002/jhet.5570380132","doi":"https://doi.org/10.1002/jhet.5570380132","is_oa":false,"landing_page_url":"https://doi.org/10.1002/jhet.5570380132","pdf_url":null,"source":{"id":"https://openalex.org/S46134040","display_name":"Journal of Heterocyclic Chemistry","issn_l":"0022-152X","issn":["0022-152X","1943-5193"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-c","jufo-1","norway-1","poland-40","russia-white-list-2","vabb-shw"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Heterocyclic Chemistry","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref"],"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/A5052708209","display_name":"Aleem Gangjee","orcid":"https://orcid.org/0000-0002-5513-7616","observed_orcids":["https://orcid.org/0000-0002-5513-7616"]},"institutions":[{"id":"https://openalex.org/I165102784","display_name":"Duquesne University","ror":"https://ror.org/02336z538","country_code":"US","type":"education","lineage":["https://openalex.org/I165102784"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Aleem Gangjee","raw_affiliation_strings":["Division of Medicinal Chemistry Graduate School of Pharmaceutical Sciences Duquesne University, Pittsburgh, PA 15282"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Medicinal Chemistry Graduate School of Pharmaceutical Sciences Duquesne University, Pittsburgh, PA 15282","institution_ids":["https://openalex.org/I165102784"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5010325568","display_name":"Farahnaz Mavandadi","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I165102784","display_name":"Duquesne University","ror":"https://ror.org/02336z538","country_code":"US","type":"education","lineage":["https://openalex.org/I165102784"]},{"id":"https://openalex.org/I4210136455","display_name":"FibroGen (United States)","ror":"https://ror.org/03sxe1905","country_code":"US","type":"company","lineage":["https://openalex.org/I4210136455"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Farahnaz Mavandadi","raw_affiliation_strings":["Division of Medicinal Chemistry Graduate School of Pharmaceutical Sciences Duquesne University, Pittsburgh, PA 15282","FibroGen 225 Gateway Boulevard, South San Francisco, CA 94080"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Medicinal Chemistry Graduate School of Pharmaceutical Sciences Duquesne University, Pittsburgh, PA 15282","institution_ids":["https://openalex.org/I165102784"]},{"raw_affiliation_string":"FibroGen 225 Gateway Boulevard, South San Francisco, CA 94080","institution_ids":["https://openalex.org/I4210136455"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5071627490","display_name":"Sherry F. Queener","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I4388446366","display_name":"Indiana University Indianapolis","ror":"https://ror.org/03eftgw80","country_code":"US","type":"education","lineage":["https://openalex.org/I4388446366","https://openalex.org/I592451"]},{"id":"https://openalex.org/I4394709130","display_name":"Indiana University School of Medicine","ror":"https://ror.org/02ets8c94","country_code":"US","type":"education","lineage":["https://openalex.org/I4394709130","https://openalex.org/I592451"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Sherry F. Queener","raw_affiliation_strings":["Department of Pharmacology and Toxicology School of Medicine, Indiana University, Indianapolis, IN 46202"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Pharmacology and Toxicology School of Medicine, Indiana University, Indianapolis, IN 46202","institution_ids":["https://openalex.org/I4388446366","https://openalex.org/I4394709130"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":4,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":3400,"currency":"USD","value_usd":3400},"apc_paid":null,"fwci":0.2577,"has_fulltext":false,"cited_by_count":4,"citation_normalized_percentile":{"value":0.54617995,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":null,"biblio":{"volume":"38","issue":"1","first_page":"213","last_page":"220"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10274","display_name":"Heterocyclic Compound Synthesis and Bioactivity","score":0.5023999810218811,"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/T10274","display_name":"Heterocyclic Compound Synthesis and Bioactivity","score":0.5023999810218811,"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":0.36719998717308044,"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/T13208","display_name":"Synthesis of heterocyclic compounds","score":0.03099999949336052,"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/trimetrexate","display_name":"trimetrexate","score":0.6990000009536743},{"id":"https://openalex.org/keywords/dihydrofolate-reductase-inhibitors","display_name":"dihydrofolate reductase inhibitors","score":0.8899999856948853},{"id":"https://openalex.org/keywords/antifolate-drugs","display_name":"antifolate","score":0.8080000281333923},{"id":"https://openalex.org/keywords/conformational-restriction","display_name":"conformational restriction","score":0.8429999947547913},{"id":"https://openalex.org/keywords/pneumocystis-carinii","display_name":"Pneumocystis carinii","score":0.9020000100135803},{"id":"https://openalex.org/keywords/toxoplasma-gondii","display_name":"Toxoplasma gondii","score":1.0},{"id":"https://openalex.org/keywords/enzyme-selectivity","display_name":"enzyme selectivity","score":0.828000009059906},{"id":"https://openalex.org/keywords/2-4-6-triaminopyrimidine","display_name":"2,4,6-triaminopyrimidine","score":0.8899999856948853},{"id":"https://openalex.org/keywords/borane-reduction","display_name":"borane reduction","score":0.5690000057220459},{"id":"https://openalex.org/keywords/lactam-reduction","display_name":"lactam reduction","score":0.6069999933242798},{"id":"https://openalex.org/keywords/beta-keto-esters","display_name":"\u03b2-keto esters","score":0.6190000176429749}],"concepts":[{"id":"https://openalex.org/C2781320022","wikidata":"https://www.wikidata.org/wiki/Q417149","display_name":"Dihydrofolate reductase","level":3,"score":0.9561476707458496},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8808692693710327},{"id":"https://openalex.org/C2993443204","wikidata":"https://www.wikidata.org/wiki/Q134478","display_name":"Pneumocystis carinii","level":4,"score":0.7079379558563232},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.6929808855056763},{"id":"https://openalex.org/C2779321679","wikidata":"https://www.wikidata.org/wiki/Q207722","display_name":"Pyrimidine","level":2,"score":0.6679404973983765},{"id":"https://openalex.org/C2781081902","wikidata":"https://www.wikidata.org/wiki/Q3539074","display_name":"Tricyclic","level":2,"score":0.5955336689949036},{"id":"https://openalex.org/C2776131168","wikidata":"https://www.wikidata.org/wiki/Q251124","display_name":"Lactam","level":2,"score":0.5897945761680603},{"id":"https://openalex.org/C2781382166","wikidata":"https://www.wikidata.org/wiki/Q50573407","display_name":"Antifolate","level":4,"score":0.5658385753631592},{"id":"https://openalex.org/C2776980637","wikidata":"https://www.wikidata.org/wiki/Q427492","display_name":"Enzyme inhibitor","level":3,"score":0.5139017105102539},{"id":"https://openalex.org/C134651460","wikidata":"https://www.wikidata.org/wiki/Q3100717","display_name":"Reductase","level":3,"score":0.4890959858894348},{"id":"https://openalex.org/C24961977","wikidata":"https://www.wikidata.org/wiki/Q225972","display_name":"Bicyclic molecule","level":2,"score":0.43821507692337036},{"id":"https://openalex.org/C181199279","wikidata":"https://www.wikidata.org/wiki/Q8047","display_name":"Enzyme","level":2,"score":0.39314699172973633},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.19423088431358337},{"id":"https://openalex.org/C2778397455","wikidata":"https://www.wikidata.org/wiki/Q50429865","display_name":"Antimetabolite","level":3,"score":0.18933087587356567},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.10097497701644897},{"id":"https://openalex.org/C3013748606","wikidata":"https://www.wikidata.org/wiki/Q15787","display_name":"Human immunodeficiency virus (HIV)","level":2,"score":0.0533234179019928},{"id":"https://openalex.org/C29730261","wikidata":"https://www.wikidata.org/wiki/Q274160","display_name":"Toxicity","level":2,"score":0.05288401246070862},{"id":"https://openalex.org/C159047783","wikidata":"https://www.wikidata.org/wiki/Q7215","display_name":"Virology","level":1,"score":0.04745703935623169},{"id":"https://openalex.org/C86803240","wikidata":"https://www.wikidata.org/wiki/Q420","display_name":"Biology","level":0,"score":0.04563954472541809},{"id":"https://openalex.org/C2777559004","wikidata":"https://www.wikidata.org/wiki/Q134478","display_name":"Pneumocystis jirovecii","level":3,"score":0.0}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1002/jhet.5570380132","doi":"https://doi.org/10.1002/jhet.5570380132","is_oa":false,"landing_page_url":"https://doi.org/10.1002/jhet.5570380132","pdf_url":null,"source":{"id":"https://openalex.org/S46134040","display_name":"Journal of Heterocyclic Chemistry","issn_l":"0022-152X","issn":["0022-152X","1943-5193"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-c","jufo-1","norway-1","poland-40","russia-white-list-2","vabb-shw"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Heterocyclic Chemistry","raw_type":"journal-article"}],"best_oa_location":null,"sustainable_development_goals":[{"score":0.504800021648407,"id":"https://metadata.un.org/sdg/3","display_name":"Good health and well-being"}],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":39,"referenced_works":["https://openalex.org/W58336000","https://openalex.org/W1579562694","https://openalex.org/W1964528315","https://openalex.org/W1966428816","https://openalex.org/W1971632719","https://openalex.org/W1979239212","https://openalex.org/W1988040540","https://openalex.org/W1992213763","https://openalex.org/W1994946938","https://openalex.org/W1995161323","https://openalex.org/W1998086369","https://openalex.org/W2003703135","https://openalex.org/W2004398073","https://openalex.org/W2012216695","https://openalex.org/W2022331577","https://openalex.org/W2028017747","https://openalex.org/W2033709335","https://openalex.org/W2037013726","https://openalex.org/W2039197900","https://openalex.org/W2049934743","https://openalex.org/W2055025009","https://openalex.org/W2060463809","https://openalex.org/W2061570337","https://openalex.org/W2068095405","https://openalex.org/W2069771713","https://openalex.org/W2094429937","https://openalex.org/W2106951092","https://openalex.org/W2122453812","https://openalex.org/W2122784237","https://openalex.org/W2145573477","https://openalex.org/W2158292139","https://openalex.org/W2165618252","https://openalex.org/W2331878978","https://openalex.org/W2418346808","https://openalex.org/W2462390644","https://openalex.org/W2950749613","https://openalex.org/W2952399205","https://openalex.org/W2952497157","https://openalex.org/W4297882644"],"related_works":["https://openalex.org/W2045138418","https://openalex.org/W314900776","https://openalex.org/W1971632719","https://openalex.org/W2951500798","https://openalex.org/W2415020765","https://openalex.org/W2951623601","https://openalex.org/W2073651191","https://openalex.org/W2421034601","https://openalex.org/W2061570337","https://openalex.org/W2949675606"],"abstract_inverted_index":{"Abstract":[0],"The":[1,36,55],"effect":[2],"of":[3,6,15,48,62,79],"conformational":[4],"restriction":[5],"the":[7,45,49,63],"C9\u2010N10":[8],"bridge":[9],"on":[10],"inhibitory":[11],"potency":[12],"and":[13,30,40,73,87,103],"selectivity":[14],"trimetrexate":[16,97,108],"against":[17,98,109],"dihydrofolate":[18,80,101,112,118],"reductase,":[19],"was":[20,58],"studied.":[21],"Specifically":[22],"three":[23,91],"nonclassical":[24],"tricyclic":[25,37],"1,3\u2010diamino\u20108\u2010(3\u2032,4\u2032,5\u2032\u2010trimethoxybenzyl)\u20107,9\u2010dihydro\u2010pyrrolo[3,4\u2010c]pyrido[2,3\u2010d]pyrimidin\u20106(5H,8H)\u2010one":[26],"(4),":[27],"1,3\u2010diamino\u20108\u2010(3\u2032,4\u2032,5\u2032\u2010trimethoxybenzyl)\u20109\u2010hydro\u2010pyrrolo[3,4\u2010c]pyrido[2,3\u2010d]pyrimidin\u20106\u2010(8H)\u2010one":[28],"(5)":[29],"1,3\u2010diamino\u2010(8H)\u2010(3\u2032,4\u2032,5\u2032\u2010trimethoxybenzyl)\u20107,9\u2010dihydro\u2010pyrrolo[3,4\u2010c]pyrido[2,3\u2010d]pyrimidine":[31],"(7)":[32],"antifolates":[33],"were":[34,42,75,93],"synthesized.":[35],"analogues":[38],"4":[39,65],"5":[41,72],"obtained":[43,59],"via":[44,60],"regiospecific":[46],"cyclo\u2010condensation":[47],"\u03b2\u2010keto":[50],"ester":[51],"17":[52],"with":[53,66,115],"2,4,6\u2010triaminopyrimidine.":[54],"analogue":[56],"7":[57,74],"reduction":[61],"lactam":[64],"borane":[67],"in":[68],"tetrahydrofuran.":[69],"Compounds":[70],"4,":[71],"evaluated":[76],"as":[77],"inhibitors":[78],"reductase":[81,102,113],"from":[82],"Pneumocystis":[83,99],"carinii,":[84],"Toxoplasma":[85,110],"gondii":[86,111],"rat":[88,116],"liver.":[89],"All":[90],"compounds":[92],"more":[94,105],"selective":[95,106],"than":[96,107],"carinii":[100],"significantly":[104],"compared":[114],"liver":[117],"reductase.":[119]},"counts_by_year":[],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2019-06-27T00:00:00"}