{"id":"https://openalex.org/W1976370087","doi":"https://doi.org/10.1039/p19940000179","title":"Synthesis of (5R)-(Z)-6-(1-methyl-1,2,3-triazol-4-ylmethylene)penem-3-carboxylic acid, a potent broad spectrum \u03b2-lactamase inhibitor, from 6-aminopenicillanic acid","display_name":"Synthesis of (5R)-(Z)-6-(1-methyl-1,2,3-triazol-4-ylmethylene)penem-3-carboxylic acid, a potent broad spectrum \u03b2-lactamase inhibitor, from 6-aminopenicillanic acid","publication_year":1994,"publication_date":"1994-01-01","ids":{"openalex":"https://openalex.org/W1976370087","doi":"https://doi.org/10.1039/p19940000179","mag":"1976370087"},"language":"en","primary_location":{"id":"doi:10.1039/p19940000179","doi":"https://doi.org/10.1039/p19940000179","is_oa":false,"landing_page_url":"https://doi.org/10.1039/p19940000179","pdf_url":null,"source":{"id":"https://openalex.org/S955628534","display_name":"Journal of the Chemical Society Perkin Transactions 1","issn_l":"1364-5463","issn":["1364-5463","1470-4358","1472-7781","2050-8263"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","norway-1"],"host_organization":"https://openalex.org/P4310320556","host_organization_name":"Royal Society of Chemistry","host_organization_lineage":["https://openalex.org/P4310320556"],"host_organization_lineage_names":["Royal Society of Chemistry"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"J. Chem. Soc., Perkin Trans. 1","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/A5027316976","display_name":"Neal F. Osborne","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Neal F. Osborne","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5065373331","display_name":"Richard J. Atkins","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Richard J. Atkins","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5013131123","display_name":"NIGEL J. P. BROOM","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Nigel J. P. Broom","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5005965572","display_name":"Steven Coulton","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Steven Coulton","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5058407374","display_name":"John B. Harbridge","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"John B. Harbridge","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":null,"display_name":"Michael A. Harris","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Michael A. Harris","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5023496329","display_name":"Irene Stirling","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Irene Stirling-Fran\u00e7ois","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"last","author":{"id":null,"display_name":"Graham Walker","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Graham Walker","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]}],"institutions":[],"countries_distinct_count":0,"institutions_distinct_count":0,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":null,"apc_paid":null,"fwci":0.8907,"has_fulltext":false,"cited_by_count":16,"citation_normalized_percentile":{"value":0.65245203,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":95},"biblio":{"volume":null,"issue":"2","first_page":"179","last_page":"188"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13489","display_name":"Synthesis of \u03b2-Lactam Compounds","score":0.9994999766349792,"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/T13489","display_name":"Synthesis of \u03b2-Lactam Compounds","score":0.9994999766349792,"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":9.999999747378752e-05,"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/T12410","display_name":"Structural and Chemical Analysis of Organic and Inorganic Compounds","score":0.0,"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/beta-lactamase-inhibitors","display_name":"beta-lactamase inhibitors","score":0.9010000228881836},{"id":"https://openalex.org/keywords/6-aminopenicillanic-acid","display_name":"6-aminopenicillanic acid","score":0.9879999756813049},{"id":"https://openalex.org/keywords/stereoselective-synthesis","display_name":"stereoselective synthesis","score":0.871999979019165},{"id":"https://openalex.org/keywords/ozonolysis","display_name":"ozonolysis","score":0.7889999747276306},{"id":"https://openalex.org/keywords/reductive-elimination","display_name":"reductive elimination","score":0.6819999814033508},{"id":"https://openalex.org/keywords/synergistic-antibacterial-activity","display_name":"synergistic antibacterial activity","score":0.6629999876022339}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.7418603301048279},{"id":"https://openalex.org/C3020442560","wikidata":"https://www.wikidata.org/wiki/Q4971815","display_name":"Broad spectrum","level":2,"score":0.701302707195282},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.35268735885620117},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.27250945568084717}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1039/p19940000179","doi":"https://doi.org/10.1039/p19940000179","is_oa":false,"landing_page_url":"https://doi.org/10.1039/p19940000179","pdf_url":null,"source":{"id":"https://openalex.org/S955628534","display_name":"Journal of the Chemical Society Perkin Transactions 1","issn_l":"1364-5463","issn":["1364-5463","1470-4358","1472-7781","2050-8263"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","norway-1"],"host_organization":"https://openalex.org/P4310320556","host_organization_name":"Royal Society of Chemistry","host_organization_lineage":["https://openalex.org/P4310320556"],"host_organization_lineage_names":["Royal Society of Chemistry"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"J. Chem. Soc., Perkin Trans. 1","raw_type":"journal-article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":29,"referenced_works":["https://openalex.org/W1970268312","https://openalex.org/W1978165995","https://openalex.org/W1984336674","https://openalex.org/W1986515168","https://openalex.org/W2001542510","https://openalex.org/W2008521081","https://openalex.org/W2022938231","https://openalex.org/W2025117137","https://openalex.org/W2027445856","https://openalex.org/W2039873333","https://openalex.org/W2044664623","https://openalex.org/W2083961141","https://openalex.org/W2091133500","https://openalex.org/W2093371346","https://openalex.org/W2097428141","https://openalex.org/W2122127499","https://openalex.org/W2312604316","https://openalex.org/W2318071147","https://openalex.org/W2319648046","https://openalex.org/W2319651383","https://openalex.org/W2322392017","https://openalex.org/W2324789874","https://openalex.org/W2326215350","https://openalex.org/W2469771205","https://openalex.org/W2950989821","https://openalex.org/W3005223649","https://openalex.org/W3005421468","https://openalex.org/W4205901932","https://openalex.org/W4299514453"],"related_works":["https://openalex.org/W2044664623","https://openalex.org/W2951575279","https://openalex.org/W2949967392","https://openalex.org/W1991137850","https://openalex.org/W2069794983","https://openalex.org/W2040645582","https://openalex.org/W2398368073","https://openalex.org/W2063997562","https://openalex.org/W2953177152","https://openalex.org/W2327784496"],"abstract_inverted_index":{"(5R)-(Z)-6-(1-Methyl-1,2,3-triazol-4-ylmethylene)penem-3-carboxylic":[0],"acid":[1,9,123],"34(BRL":[2,124],"42715)":[3,125],"has":[4],"been":[5],"prepared":[6],"from":[7],"6-aminopenicillanic":[8],"4(6-APA)":[10],"by":[11,34,38,54,69,135],"a":[12,89,102,127,159],"short,":[13],"stereoselective":[14],"and":[15,85,107,112,144],"efficient":[16],"route":[17],"via":[18],"the":[19,30,42,50,57,62,72],"novel":[20],"intermediate,":[21],"p-methoxybenzyl":[22],"(5R,":[23],"6S)-6-bromopenem-3-carboxylate":[24],"17.Elaboration":[25],"of":[26,49,56,71,78,92,98,105,118,141,162],"6-APA":[27],"4":[28],"to":[29,61],"azetidinone":[31],"disulfide":[32],"10":[33],"established":[35],"methodology,":[36],"followed":[37],"reductive":[39,96],"formylation":[40],"provided":[41,121],"crystalline":[43,63,128],"C-4":[44],"formylthio-azetidinone":[45],"derivative":[46,59],"29.":[47],"Cyclization":[48],"oxalimide":[51],"28,":[52],"obtained":[53],"ozonolysis":[55],"formylthio":[58],"29,":[60],"6\u03b1-bromopenem":[64],"ester":[65,119],"17":[66,80],"was":[67],"effected":[68],"way":[70],"phosphite-mediated":[73],"carbonyl\u2013carbonyl":[74],"coupling":[75],"reaction.Sequential":[76],"treatment":[77],"bromopenem":[79],"with":[81,147],"lithium":[82],"diphenylamide,":[83],"1-methyl-1,2,3-triazole-4-carbaldehyde,":[84],"acetic":[86],"anhydride":[87],"gave":[88],"diastereoisomeric":[90],"mixture":[91,100,104],"acylated":[93],"bromohydrins":[94],"32;":[95],"elimination":[97],"this":[99],"afforded":[101],"separable":[103],"(Z)-":[106],"(E)-triazolylmethylene":[108],"penem":[109],"esters,":[110],"33":[111,120],"35":[113],"respectively.":[114],"Lewis":[115],"acid-mediated":[116],"deprotection":[117],"(5R)(Z)-6-(1-methyl-1,2,3-triazol-4-ylmethylene)penem-3-carboxylic":[122],"as":[126],"sodium":[129],"salt":[130],"monohydrate.The":[131],"6-heterocyclylmethylene":[132],"penems,":[133],"represented":[134],"BRL":[136],"42715,":[137],"are":[138],"potent":[139],"inhibitors":[140],"bacterial":[142],"\u03b2-lactamases":[143],"their":[145],"combination":[146],"an":[148],"appropriate":[149],"penicillin":[150],"or":[151],"cephalosporin":[152],"results":[153],"in":[154],"good":[155],"synergistic":[156],"activity":[157],"against":[158],"broad":[160],"range":[161],"\u03b2-lactamase-producing":[163],"bacteria.":[164]},"counts_by_year":[{"year":2021,"cited_by_count":2},{"year":2020,"cited_by_count":1},{"year":2018,"cited_by_count":1}],"updated_date":"2026-10-14T16:39:01.820549","created_date":"2016-06-24T00:00:00"}