{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,16]],"date-time":"2026-06-16T22:32:02Z","timestamp":1781649122938,"version":"3.54.5"},"reference-count":47,"publisher":"Wiley","issue":"11","license":[{"start":{"date-parts":[[2024,1,11]],"date-time":"2024-01-11T00:00:00Z","timestamp":1704931200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP21K15218, JP23K14315"],"award-info":[{"award-number":["JP21K15218, JP23K14315"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100009619","name":"Japan Agency for Medical Research and Development","doi-asserted-by":"publisher","award":["JP22ama121040j0001"],"award-info":[{"award-number":["JP22ama121040j0001"]}],"id":[{"id":"10.13039\/100009619","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2024,2,21]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We herein evaluate a biological applicability of 1,3\u2010substituted cuneanes as an isostere of <jats:italic>m<\/jats:italic>\u2010substituted benzenes based on its structural similarity. An investigation of a method to obtain 1,3\u2010substituted cuneanes by selective isomerization of 1,4\u2010substituted cubanes enables this attempt by giving a key synthetic step to obtain a cuneane analogs of pharmaceuticals having <jats:italic>m<\/jats:italic>\u2010substituted benzene moiety. Biological evaluation of the synthesized analogs and <jats:italic>in silico<\/jats:italic> study of the obtained result revealed a potential usage of cuneane skeleton in medicinal chemistry.<\/jats:p>","DOI":"10.1002\/chem.202303548","type":"journal-article","created":{"date-parts":[[2023,11,27]],"date-time":"2023-11-27T22:37:45Z","timestamp":1701124665000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["Biological Evaluation of Isosteric Applicability of 1,3\u2010Substituted Cuneanes as <i>m<\/i>\u2010Substituted Benzenes Enabled by Selective Isomerization of 1,4\u2010Substituted Cubanes"],"prefix":"10.1002","volume":"30","author":[{"given":"Kan","family":"Fujiwara","sequence":"first","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Tohoku University  6-3, Aoba, Aramaki, Aoba-ku Sendai Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9207-4423","authenticated-orcid":false,"given":"Shota","family":"Nagasawa","sequence":"additional","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Tohoku University  6-3, Aoba, Aramaki, Aoba-ku Sendai Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ryusei","family":"Maeyama","sequence":"additional","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Tohoku University  6-3, Aoba, Aramaki, Aoba-ku Sendai Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ryosuke","family":"Segawa","sequence":"additional","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Tohoku University  6-3, Aoba, Aramaki, Aoba-ku Sendai Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Noriyasu","family":"Hirasawa","sequence":"additional","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Tohoku University  6-3, Aoba, Aramaki, Aoba-ku Sendai Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takatsugu","family":"Hirokawa","sequence":"additional","affiliation":[{"name":"Division of Biomedical Science, Faculty of Medicine University of Tsukuba"},{"name":"Transborder Medical Research Center University of Tsukuba  1-1-1 Tennodai Tsukuba Ibaraki Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0679-939X","authenticated-orcid":false,"given":"Yoshiharu","family":"Iwabuchi","sequence":"additional","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Tohoku University  6-3, Aoba, Aramaki, Aoba-ku Sendai Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,1,11]]},"reference":[{"key":"e_1_2_3_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00724a061"},{"key":"e_1_2_3_2_1","unstructured":"\u00a0"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01059a072"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01069a041"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr500523x"},{"key":"e_1_2_3_6_1","unstructured":"Similar isomerizations were reported in caged hydrocarbons having partial structure of cubane see:"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)97830-X"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00711a082"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)96554-2"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)94464-8"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00838a027"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00838a023"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39940002321"},{"key":"e_1_2_3_14_1","unstructured":"Isomerization using other metals were reported. See:"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0161864"},{"key":"e_1_2_3_16_2","doi-asserted-by":"crossref","unstructured":"H. Takebe S. Matsubara Eur. J. Org. Chem.2022 2022 e202200567.","DOI":"10.1002\/ejoc.202200567"},{"key":"e_1_2_3_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo050471"},{"key":"e_1_2_3_18_1","unstructured":"Limited examples are shown. See:"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma300027k"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/cphc.202000130"},{"key":"e_1_2_3_21_1","unstructured":"Reviews;"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9OB01238A"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8OB02812E"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.1c01215"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.0c00746"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1MD00043H"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2020.129628"},{"key":"e_1_2_3_28_1","unstructured":"\u00a0"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202004183"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202000548"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c09733"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-022-05290-z"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-022-33827-3"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-023-06021-8"},{"key":"e_1_2_3_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c03144"},{"key":"e_1_2_3_36_1","unstructured":"See Supporting Information for details."},{"key":"e_1_2_3_37_1","unstructured":"During preparation of the manuscript two different research groups independently reported the silver(I)-catalyzed or mediated selective isomerization of 1 4-substituted cubanes into 1 3- or 2 6-substituted cuneanes and suggested its use as an isostere of benzene ring into ChemRxiv and they appeared as a peer-reviewed papers. Our investigation about the isomerization reaction of substituted cubanes into cuneanes is consistent with their reports. See;"},{"key":"e_1_2_3_38_2","unstructured":"J.-Y. Son S. Aikonen N. Morgan A.\u2005S. Harmata J.\u2005J. Sabatini R.\u2005C. Sausa E.\u2005F.\u2005C. Byrd D.\u2005H. Ess R.\u2005S. Paton C.\u2005R.\u2005J. Stephenson J. Am. Chem. Soc.2023 10.1021\/jacs.3c03226 (ChemRxiv.2023 10.\u200d26434\/chemrxiv-2023-0xn9c);"},{"key":"e_1_2_3_39_2","unstructured":"E. Smith L. O'Brien K.\u2005D. Jones S.\u2005P. Argent C. Salome Q. Lefebvre A. Valery G.\u2005N. Newton H.\u2005W. Lam J. Am. Chem. Soc.2023 10.1021\/jacs.3c03207 (ChemRxiv.2023 10.\u200d26434\/chemrxiv-2023-l8q0t)."},{"key":"e_1_2_3_40_1","unstructured":"We have deposited this manuscript to ChemRxiv as follows. K. Fujiwara S. Nagasawa R. Maeyama R. Segawa N. Hirasawa T. Hirokawa Y. Iwabuchi ChemRxiv2023 doi:10.26434\/chemrxiv-2023-fgxxm-v2. The initial version was uploaded 10 May 2023 and it was updated 26 July 2023."},{"key":"e_1_2_3_41_1","doi-asserted-by":"publisher","DOI":"10.1002\/pi.5691"},{"key":"e_1_2_3_42_1","doi-asserted-by":"publisher","DOI":"10.1039\/c29710000040"},{"key":"e_1_2_3_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00749"},{"key":"e_1_2_3_44_1","doi-asserted-by":"publisher","DOI":"10.1039\/b822944a"},{"key":"e_1_2_3_45_1","unstructured":"\u00a0"},{"key":"e_1_2_3_46_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.220197"},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.230101"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202303548","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T08:30:31Z","timestamp":1760257831000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202303548"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,1,11]]},"references-count":47,"journal-issue":{"issue":"11","published-print":{"date-parts":[[2024,2,21]]}},"alternative-id":["10.1002\/chem.202303548"],"URL":"https:\/\/doi.org\/10.1002\/chem.202303548","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,1,11]]},"assertion":[{"value":"2023-10-30","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-01-11","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202303548"}}