{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,1]],"date-time":"2026-07-01T07:43:55Z","timestamp":1782891835893,"version":"3.54.5"},"reference-count":29,"publisher":"Royal Society of Chemistry (RSC)","issue":"37","license":[{"start":{"date-parts":[[2023,8,26]],"date-time":"2023-08-26T00:00:00Z","timestamp":1693008000000},"content-version":"am","delay-in-days":602,"URL":"http:\/\/rsc.li\/journals-terms-of-use"}],"funder":[{"DOI":"10.13039\/501100002322","name":"Coordena\u00e7\u00e3o de Aperfei\u00e7oamento de Pessoal de N\u00edvel Superior","doi-asserted-by":"publisher","award":["SVR 119\/2012"],"award-info":[{"award-number":["SVR 119\/2012"]}],"id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100013870","name":"Astex Pharmaceuticals","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100013870","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001807","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado de S\u00e3o Paulo","doi-asserted-by":"publisher","award":["#2013\/26485-0"],"award-info":[{"award-number":["#2013\/26485-0"]}],"id":[{"id":"10.13039\/501100001807","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001807","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado de S\u00e3o Paulo","doi-asserted-by":"publisher","award":["#2016\/24817-4"],"award-info":[{"award-number":["#2016\/24817-4"]}],"id":[{"id":"10.13039\/501100001807","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001807","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado de S\u00e3o Paulo","doi-asserted-by":"publisher","award":["#2017\/21146-6"],"award-info":[{"award-number":["#2017\/21146-6"]}],"id":[{"id":"10.13039\/501100001807","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Desenvolvimento Cient\u00edfico e Tecnol\u00f3gico","doi-asserted-by":"publisher","award":["313834\/2018-0"],"award-info":[{"award-number":["313834\/2018-0"]}],"id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Desenvolvimento Cient\u00edfico e Tecnol\u00f3gico","doi-asserted-by":"publisher","award":["428527\/2016-7"],"award-info":[{"award-number":["428527\/2016-7"]}],"id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["rsc.org"],"crossmark-restriction":true},"short-container-title":["Org. Biomol. Chem."],"abstract":"<jats:p>The expansion of the fragment chemical space by accessing growth vectors of two \u201cheteroaromatic rings of the future\u201d with regioselective functionalization is reported.<\/jats:p>","DOI":"10.1039\/d2ob00968d","type":"journal-article","created":{"date-parts":[[2022,8,26]],"date-time":"2022-08-26T11:00:46Z","timestamp":1661511646000},"page":"7483-7490","update-policy":"https:\/\/doi.org\/10.1039\/rsc_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Growth vector elaboration of fragments: regioselective functionalization of 5-hydroxy-6-azaindazole and 3-hydroxy-2,6-naphthyridine"],"prefix":"10.1039","volume":"20","author":[{"given":"Paulo","family":"Eliandro da Silva J\u00fanior","sequence":"first","affiliation":[{"name":"Faculdade de Ci\u00eancias Farmac\u00eauticas de Ribeir\u00e3o Preto, Departmento de Ci\u00eancias Farmac\u00eauticas, Universidade de S\u00e3o Paulo, Ribeir\u00e3o Preto 14040-903, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shaiani Maria Gil","family":"de Melo","sequence":"additional","affiliation":[{"name":"Faculdade de Ci\u00eancias Farmac\u00eauticas de Ribeir\u00e3o Preto, Departmento de Ci\u00eancias Farmac\u00eauticas, Universidade de S\u00e3o Paulo, Ribeir\u00e3o Preto 14040-903, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Murilo Helder","family":"de Paula","sequence":"additional","affiliation":[{"name":"Faculdade de Ci\u00eancias Farmac\u00eauticas de Ribeir\u00e3o Preto, Departmento de Ci\u00eancias Farmac\u00eauticas, Universidade de S\u00e3o Paulo, Ribeir\u00e3o Preto 14040-903, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ricardo","family":"Vessecchi","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Faculdade de Filosofia, Ci\u00eancias e Letras de Ribeir\u00e3o Preto, Universidade de S\u00e3o Paulo, Av. Bandeirantes, 3900, Ribeir\u00e3o Preto, SP, 14040-901, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3266-4050","authenticated-orcid":false,"given":"Till","family":"Opatz","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, Mainz 55128, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"James E. H.","family":"Day","sequence":"additional","affiliation":[{"name":"Astex Pharmaceuticals, 436 Cambridge Science Park, Milton Road, Cambridge CB4 0QA, UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4862-7999","authenticated-orcid":false,"given":"A.","family":"Ganesan","sequence":"additional","affiliation":[{"name":"School of Pharmacy, University of East Anglia, Norwich Research Park, Norwich NR4 7TJ, UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8652-7123","authenticated-orcid":false,"given":"Flavio","family":"da Silva Emery","sequence":"additional","affiliation":[{"name":"Faculdade de Ci\u00eancias Farmac\u00eauticas de Ribeir\u00e3o Preto, Departmento de Ci\u00eancias Farmac\u00eauticas, Universidade de S\u00e3o Paulo, Ribeir\u00e3o Preto 14040-903, Brazil"},{"name":"Center for the Research and Advancement in Fragments and molecular Targets (CRAFT), Faculdade de Ci\u00eancias Farmac\u00eauticas de Ribeir\u00e3o Preto, Universidade de S\u00e3o Paulo, RIbeir\u00e3o Preto, S\u00e3o Paulo, Brasil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"292","published-online":{"date-parts":[[2022]]},"reference":[{"key":"D2OB00968D\/cit1a\/1","doi-asserted-by":"crossref","first-page":"2265","DOI":"10.3762\/bjoc.9.265","volume":"9","author":"Baumann","year":"2013","journal-title":"Beilstein J. Org. Chem."},{"key":"D2OB00968D\/cit1b\/1","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1007\/s10593-012-0960-z","volume":"48","author":"Gomtsyan","year":"2012","journal-title":"Chem. Heterocycl. Compd."},{"issue":"9","key":"D2OB00968D\/cit1c\/1","doi-asserted-by":"crossref","first-page":"2952","DOI":"10.1021\/jm801513z","volume":"52","author":"Pitt","year":"2009","journal-title":"J. Med. Chem."},{"key":"D2OB00968D\/cit1d\/1","first-page":"384","author":"Passador","year":"2019","journal-title":"Synthesis"},{"key":"D2OB00968D\/cit2\/1","doi-asserted-by":"crossref","first-page":"22777","DOI":"10.1039\/C6RA01099G","volume":"6","author":"Silva Junior","year":"2016","journal-title":"RSC Adv."},{"issue":"9","key":"D2OB00968D\/cit3\/1","doi-asserted-by":"crossref","first-page":"605","DOI":"10.1038\/nrd.2016.109","volume":"15","author":"Erlanson","year":"2016","journal-title":"Nat. Rev. Drug Discovery"},{"key":"D2OB00968D\/cit4a\/1","first-page":"371","volume":"50","author":"Davis","year":"2017","journal-title":"Annu. Rep. Med. Chem."},{"issue":"5","key":"D2OB00968D\/cit4b\/1","doi-asserted-by":"crossref","first-page":"1599","DOI":"10.1039\/C5OB02461G","volume":"14","author":"Palmer","year":"2016","journal-title":"Org. Biomol. Chem."},{"issue":"19","key":"D2OB00968D\/cit4c\/1","doi-asserted-by":"crossref","first-page":"13980","DOI":"10.1021\/acs.jmedchem.1c00787","volume":"64","author":"Vaidergorn","year":"2021","journal-title":"J. Med. Chem."},{"issue":"8","key":"D2OB00968D\/cit5\/1","doi-asserted-by":"crossref","first-page":"644","DOI":"10.1038\/nrd3926-c1","volume":"12","author":"Jhoti","year":"2013","journal-title":"Nat. Rev. Drug Discovery"},{"issue":"2","key":"D2OB00968D\/cit6\/1","doi-asserted-by":"crossref","first-page":"488","DOI":"10.1002\/anie.201506783","volume":"55","author":"Murray","year":"2016","journal-title":"Angew. Chem., Int. Ed."},{"issue":"14","key":"D2OB00968D\/cit7\/1","doi-asserted-by":"crossref","first-page":"6440","DOI":"10.1021\/acs.jmedchem.7b00809","volume":"60","author":"Hall","year":"2017","journal-title":"J. Med. Chem."},{"key":"D2OB00968D\/cit8\/1","doi-asserted-by":"crossref","first-page":"81","DOI":"10.1055\/s-2006-958936","author":"Krasnokutskaya","year":"2007","journal-title":"Synthesis"},{"issue":"60","key":"D2OB00968D\/cit9\/1","doi-asserted-by":"crossref","first-page":"6767","DOI":"10.1039\/c3cc43279c","volume":"49","author":"Ke","year":"2013","journal-title":"Chem. Commun."},{"issue":"3","key":"D2OB00968D\/cit10\/1","doi-asserted-by":"crossref","first-page":"1170","DOI":"10.1021\/cr100209d","volume":"111","author":"Le Bras","year":"2011","journal-title":"Chem. Rev."},{"issue":"2","key":"D2OB00968D\/cit11\/1","doi-asserted-by":"crossref","first-page":"165","DOI":"10.2174\/1385272821666171002121126","volume":"22","author":"Heravi","year":"2018","journal-title":"Curr. Org. Chem."},{"key":"D2OB00968D\/cit12\/1","doi-asserted-by":"crossref","first-page":"862","DOI":"10.1002\/ejoc.200900849","author":"El Akkaoui","year":"2010","journal-title":"Eur. J. Org. Chem."},{"issue":"38","key":"D2OB00968D\/cit13\/1","doi-asserted-by":"crossref","first-page":"13194","DOI":"10.1021\/ja1066459","volume":"132","author":"Seiple","year":"2010","journal-title":"J. Am. Chem. Soc."},{"issue":"11","key":"D2OB00968D\/cit14\/1","doi-asserted-by":"crossref","first-page":"4287","DOI":"10.1021\/ja412563e","volume":"136","author":"Larsen","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"D2OB00968D\/cit15\/1","doi-asserted-by":"crossref","first-page":"7318","DOI":"10.1039\/C4OB01565G","volume":"12","author":"Sadler","year":"2014","journal-title":"Org. Biomol. Chem."},{"issue":"38","key":"D2OB00968D\/cit16\/1","doi-asserted-by":"crossref","first-page":"12231","DOI":"10.1021\/jacs.5b06758","volume":"137","author":"Gao","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"D2OB00968D\/cit17\/1","doi-asserted-by":"crossref","first-page":"95","DOI":"10.1038\/nature11680","volume":"492","author":"Fujiwara","year":"2012","journal-title":"Nature"},{"key":"D2OB00968D\/cit18\/1","doi-asserted-by":"crossref","first-page":"22","DOI":"10.1039\/C7SC04509C","volume":"9","author":"Hirano","year":"2018","journal-title":"Chem. Sci."},{"key":"D2OB00968D\/cit19\/1","doi-asserted-by":"crossref","first-page":"109","DOI":"10.1039\/C5RA20954D","volume":"6","author":"Chauhan","year":"2016","journal-title":"RSC Adv."},{"issue":"6","key":"D2OB00968D\/cit20\/1","doi-asserted-by":"crossref","first-page":"1077","DOI":"10.1021\/cr50030a004","volume":"59","author":"Searles","year":"1959","journal-title":"Chem. Rev."},{"key":"D2OB00968D\/cit21\/1","doi-asserted-by":"crossref","first-page":"10434","DOI":"10.1039\/c2cc35757g","volume":"48","author":"Prasad","year":"2012","journal-title":"Chem. Commun."},{"key":"D2OB00968D\/cit22\/1","doi-asserted-by":"crossref","first-page":"8791","DOI":"10.1039\/C7NJ01709J","volume":"41","author":"Laha","year":"2017","journal-title":"New J. Chem."},{"issue":"3","key":"D2OB00968D\/cit23a\/1","doi-asserted-by":"crossref","first-page":"546","DOI":"10.1039\/C5CS00628G","volume":"45","author":"Cernak","year":"2016","journal-title":"Chem. Soc. Rev."},{"issue":"38","key":"D2OB00968D\/cit23b\/1","doi-asserted-by":"crossref","first-page":"8744","DOI":"10.1039\/C9SC03691A","volume":"10","author":"Dong","year":"2019","journal-title":"Chem. Sci."}],"container-title":["Organic &amp; Biomolecular Chemistry"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/pubs.rsc.org\/en\/content\/articlepdf\/2022\/OB\/D2OB00968D","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,7,1]],"date-time":"2026-07-01T05:53:27Z","timestamp":1782885207000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.rsc.org\/ob\/article\/20\/37\/7483-7490\/778613"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022]]},"references-count":29,"journal-issue":{"issue":"37","published-print":{"date-parts":[[2022,9,28]]}},"URL":"https:\/\/doi.org\/10.1039\/d2ob00968d","relation":{},"ISSN":["1477-0520","1477-0539"],"issn-type":[{"value":"1477-0520","type":"print"},{"value":"1477-0539","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022]]}}}