{"id":"https://openalex.org/W2046129704","doi":"https://doi.org/10.1021/jo0352068","title":"Novel Chimeric Scaffolds to Extend the Exploration of Receptor Space: Hybrid \u03b2- d -Glucose\u2212Benzoheterodiazepine Structures for Broad Screening. Effect of Amide Alkylation on the Course of Cyclization Reactions","display_name":"Novel Chimeric Scaffolds to Extend the Exploration of Receptor Space: Hybrid \u03b2- d -Glucose\u2212Benzoheterodiazepine Structures for Broad Screening. Effect of Amide Alkylation on the Course of Cyclization Reactions","publication_year":2003,"publication_date":"2003-12-19","ids":{"openalex":"https://openalex.org/W2046129704","doi":"https://doi.org/10.1021/jo0352068","mag":"2046129704","pmid":"https://pubmed.ncbi.nlm.nih.gov/14725439"},"language":"en","primary_location":{"id":"doi:10.1021/jo0352068","doi":"https://doi.org/10.1021/jo0352068","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo0352068","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","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":"The Journal of Organic 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/A5078992604","display_name":"Le\u00efla Abrous","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I79576946","display_name":"University of Pennsylvania","ror":"https://ror.org/00b30xv10","country_code":"US","type":"education","lineage":["https://openalex.org/I79576946"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Le\u00efla Abrous","raw_affiliation_strings":["University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323","University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323","institution_ids":["https://openalex.org/I79576946"]},{"raw_affiliation_string":"University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA","institution_ids":["https://openalex.org/I79576946"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5048672500","display_name":"Patrick A. Jokiel","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I79576946","display_name":"University of Pennsylvania","ror":"https://ror.org/00b30xv10","country_code":"US","type":"education","lineage":["https://openalex.org/I79576946"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Patrick A. Jokiel","raw_affiliation_strings":["University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323","institution_ids":["https://openalex.org/I79576946"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5055084607","display_name":"Sarah R. Friedrich","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I79576946","display_name":"University of Pennsylvania","ror":"https://ror.org/00b30xv10","country_code":"US","type":"education","lineage":["https://openalex.org/I79576946"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Sarah R. Friedrich","raw_affiliation_strings":["University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323","institution_ids":["https://openalex.org/I79576946"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5056190867","display_name":"John Jr. Hynes","orcid":"https://orcid.org/0000-0002-0490-5179","observed_orcids":["https://orcid.org/0000-0002-0490-5179"]},"institutions":[{"id":"https://openalex.org/I79576946","display_name":"University of Pennsylvania","ror":"https://ror.org/00b30xv10","country_code":"US","type":"education","lineage":["https://openalex.org/I79576946"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"John Hynes,","raw_affiliation_strings":["University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323","institution_ids":["https://openalex.org/I79576946"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5066527875","display_name":"Amos B. Smith","orcid":"https://orcid.org/0000-0002-1712-8567","observed_orcids":["https://orcid.org/0000-0002-1712-8567"]},"institutions":[{"id":"https://openalex.org/I79576946","display_name":"University of Pennsylvania","ror":"https://ror.org/00b30xv10","country_code":"US","type":"education","lineage":["https://openalex.org/I79576946"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Amos B. Smith","raw_affiliation_strings":["University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323","institution_ids":["https://openalex.org/I79576946"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5072463303","display_name":"Ralph F. Hirschmann","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I79576946","display_name":"University of Pennsylvania","ror":"https://ror.org/00b30xv10","country_code":"US","type":"education","lineage":["https://openalex.org/I79576946"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Ralph Hirschmann","raw_affiliation_strings":["University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323","institution_ids":["https://openalex.org/I79576946"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I79576946"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":1.3419,"has_fulltext":false,"cited_by_count":31,"citation_normalized_percentile":{"value":0.74573742,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":96},"biblio":{"volume":"69","issue":"2","first_page":"280","last_page":"302"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13105","display_name":"Synthesis and pharmacology of benzodiazepine derivatives","score":0.9057999849319458,"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/T13105","display_name":"Synthesis and pharmacology of benzodiazepine derivatives","score":0.9057999849319458,"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/T10835","display_name":"Carbohydrate Chemistry and Synthesis","score":0.03669999912381172,"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/T10911","display_name":"Chemical Synthesis and Analysis","score":0.024700000882148743,"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-d-glucose","display_name":"\u03b2-D-glucose","score":0.7900000214576721},{"id":"https://openalex.org/keywords/benzodiazepines","display_name":"benzodiazepines","score":0.8730000257492065},{"id":"https://openalex.org/keywords/cyclization","display_name":"cyclization","score":0.7519999742507935},{"id":"https://openalex.org/keywords/amide-bond-conformation","display_name":"amide bond conformation","score":0.7829999923706055},{"id":"https://openalex.org/keywords/dimers","display_name":"dimers","score":0.5669999718666077},{"id":"https://openalex.org/keywords/receptor-binding","display_name":"receptor binding","score":0.3269999921321869}],"concepts":[{"id":"https://openalex.org/C2778439535","wikidata":"https://www.wikidata.org/wiki/Q188777","display_name":"Amide","level":2,"score":0.6153483390808105},{"id":"https://openalex.org/C164361826","wikidata":"https://www.wikidata.org/wiki/Q177604","display_name":"Alkylation","level":3,"score":0.5017919540405273},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.49636751413345337},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.4533403217792511},{"id":"https://openalex.org/C170493617","wikidata":"https://www.wikidata.org/wiki/Q208467","display_name":"Receptor","level":2,"score":0.43607577681541443},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.2644602060317993},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.09837925434112549}],"mesh":[{"descriptor_ui":"D000478","descriptor_name":"Alkylation","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D000577","descriptor_name":"Amides","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D001569","descriptor_name":"Benzodiazepines","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D004951","descriptor_name":"Esterification","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D005947","descriptor_name":"Glucose","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D009682","descriptor_name":"Magnetic Resonance Spectroscopy","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013055","descriptor_name":"Spectrophotometry, Infrared","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013058","descriptor_name":"Mass Spectrometry","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/jo0352068","doi":"https://doi.org/10.1021/jo0352068","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo0352068","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","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":"The Journal of Organic Chemistry","raw_type":"journal-article"},{"id":"pmid:14725439","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/14725439","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":"The Journal of organic chemistry","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G8392424091","display_name":"Non-Peptide Peptidomimetics","funder_award_id":"R01GM041821","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"}],"funders":[{"id":"https://openalex.org/F4320332161","display_name":"National Institutes of Health","ror":"https://ror.org/01cwqze88"},{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":28,"referenced_works":["https://openalex.org/W172753723","https://openalex.org/W1846153720","https://openalex.org/W1964036268","https://openalex.org/W1965566437","https://openalex.org/W1979435862","https://openalex.org/W1995105459","https://openalex.org/W2000568490","https://openalex.org/W2002474622","https://openalex.org/W2003670030","https://openalex.org/W2020451444","https://openalex.org/W2025690482","https://openalex.org/W2028523928","https://openalex.org/W2036963672","https://openalex.org/W2042529958","https://openalex.org/W2043716459","https://openalex.org/W2047134066","https://openalex.org/W2051334762","https://openalex.org/W2059025265","https://openalex.org/W2061755100","https://openalex.org/W2062360632","https://openalex.org/W2084687677","https://openalex.org/W2093208632","https://openalex.org/W2097148620","https://openalex.org/W2317227212","https://openalex.org/W2949516160","https://openalex.org/W2949632495","https://openalex.org/W2952382195","https://openalex.org/W4401102731"],"related_works":["https://openalex.org/W2059025265","https://openalex.org/W7065506318","https://openalex.org/W4404761083","https://openalex.org/W2949521626","https://openalex.org/W2986641268","https://openalex.org/W2771929043","https://openalex.org/W1989297534","https://openalex.org/W1970310385","https://openalex.org/W4242554945","https://openalex.org/W2064576303"],"abstract_inverted_index":{"New":[0],"molecular":[1],"platforms":[2],"which":[3],"are":[4,113],"hybrids":[5],"of":[6,38,45,63,69,74,79,99],"two":[7],"scaffolds-namely,":[8],"beta-d-glucose":[9],"and":[10,20,35,50,57,82,119],"benzodiazepine,":[11],"each":[12],"able":[13],"to":[14,22,90],"bind":[15],"several":[16],"proteins-were":[17],"designed,":[18],"synthesized":[19],"functionalized":[21,47],"serve":[23],"as":[24],"probes":[25],"for":[26],"broad":[27,117],"biological":[28],"screening.":[29],"Herein,":[30],"we":[31],"describe":[32],"the":[33,46,53,77,92,97,100,106],"syntheses":[34],"chemical":[36],"properties":[37],"these":[39],"novel":[40],"chimeric":[41],"scaffolds.":[42],"Attempted":[43],"cyclization":[44,86,98,108],"analogues":[48],"(-)-96":[49],"(-)-97":[51],"afforded":[52,104],"corresponding":[54],"dimers":[55],"(-)-98":[56],"(-)-99,":[58],"respectively,":[59],"under":[60],"a":[61,124],"variety":[62],"reaction":[64],"conditions,":[65],"even":[66],"at":[67,122],"concentrations":[68],"only":[70,114],"0.001":[71],"N.":[72],"Consideration":[73],"factors":[75],"affecting":[76],"conformation":[78],"amide":[80,93],"bonds":[81],"their":[83],"effects":[84],"on":[85],"reactions":[87],"led":[88],"us":[89],"alkylate":[91],"bond.":[94],"As":[95],"expected,":[96],"N-methyl":[101],"derivative":[102],"(-)-110":[103],"exclusively":[105],"unimolecular":[107],"product":[109],"(+)-111.":[110],"These":[111],"compounds":[112],"now":[115],"undergoing":[116],"screening":[118],"represent":[120],"therefore":[121],"present":[123],"\"prospecting":[125],"library.\"":[126]},"counts_by_year":[{"year":2018,"cited_by_count":1},{"year":2016,"cited_by_count":1},{"year":2015,"cited_by_count":2},{"year":2013,"cited_by_count":1},{"year":2012,"cited_by_count":2}],"updated_date":"2026-11-07T11:25:07.637180","created_date":"2016-06-24T00:00:00"}