{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,19]],"date-time":"2026-10-19T22:30:42Z","timestamp":1792449042423,"version":"4.5.0"},"reference-count":100,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2024,1,22]],"date-time":"2024-01-22T00:00:00Z","timestamp":1705881600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100010663","name":"H2020 European Research Council","doi-asserted-by":"publisher","award":["101000893"],"award-info":[{"award-number":["101000893"]}],"id":[{"id":"10.13039\/100010663","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2024,2,26]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    The spiro[3.3]heptane core, with the non\u2010coplanar exit vectors, was shown to be a saturated benzene bioisostere. This scaffold was incorporated into the anticancer drug\n                    <jats:italic>sonidegib<\/jats:italic>\n                    (instead of the\n                    <jats:italic>meta<\/jats:italic>\n                    \u2010benzene), the anticancer drug\n                    <jats:italic>vorinostat<\/jats:italic>\n                    (instead of the phenyl ring), and the anesthetic drug\n                    <jats:italic>benzocaine<\/jats:italic>\n                    (instead of the\n                    <jats:italic>para<\/jats:italic>\n                    \u2010benzene). The patent\u2010free saturated analogs obtained showed a high potency in the corresponding biological assays.\n                  <\/jats:p>","DOI":"10.1002\/anie.202316557","type":"journal-article","created":{"date-parts":[[2024,1,22]],"date-time":"2024-01-22T09:10:18Z","timestamp":1705914618000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":39,"title":["Spiro[3.3]heptane as a Saturated Benzene Bioisostere**"],"prefix":"10.1002","volume":"63","author":[{"given":"Kateryna","family":"Prysiazhniuk","sequence":"first","affiliation":[{"name":"Enamine Ltd.  Winston Churchill Str. 78 02094 Kyiv Ukraine"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Oleksandr P.","family":"Datsenko","sequence":"additional","affiliation":[{"name":"Enamine Ltd.  Winston Churchill Str. 78 02094 Kyiv Ukraine"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Oleksandr","family":"Polishchuk","sequence":"additional","affiliation":[{"name":"Enamine Ltd.  Winston Churchill Str. 78 02094 Kyiv Ukraine"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stanislav","family":"Shulha","sequence":"additional","affiliation":[{"name":"Enamine Ltd.  Winston Churchill Str. 78 02094 Kyiv Ukraine"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Oleh","family":"Shablykin","sequence":"additional","affiliation":[{"name":"Enamine Ltd.  Winston Churchill Str. 78 02094 Kyiv Ukraine"},{"name":"V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry NAS of Ukraine  02094 Kyiv Ukraine"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yelyzaveta","family":"Nikandrova","sequence":"additional","affiliation":[{"name":"Bienta  Winston Churchill Str. 78 02094 Kyiv Ukraine"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kateryna","family":"Horbatok","sequence":"additional","affiliation":[{"name":"Bienta  Winston Churchill Str. 78 02094 Kyiv Ukraine"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Iryna","family":"Bodenchuk","sequence":"additional","affiliation":[{"name":"Bienta  Winston Churchill Str. 78 02094 Kyiv Ukraine"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Petro","family":"Borysko","sequence":"additional","affiliation":[{"name":"Bienta  Winston Churchill Str. 78 02094 Kyiv Ukraine"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dmytro","family":"Shepilov","sequence":"additional","affiliation":[{"name":"Bienta  Winston Churchill Str. 78 02094 Kyiv Ukraine"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Iryna","family":"Pishel","sequence":"additional","affiliation":[{"name":"Bienta  Winston Churchill Str. 78 02094 Kyiv Ukraine"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vladimir","family":"Kubyshkin","sequence":"additional","affiliation":[{"name":"Enamine Ltd.  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These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structures service."},{"key":"e_1_2_7_80_1","unstructured":"clogP was calculated with ChemAxon (version 22.13)."},{"key":"e_1_2_7_81_1","doi-asserted-by":"publisher","DOI":"10.1021\/ml1000307"},{"key":"e_1_2_7_82_1","unstructured":"By testing a racemic mixture one simultaneously tests two compounds\u2014two enantiomers."},{"key":"e_1_2_7_83_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-023-06021-8"},{"key":"e_1_2_7_84_1","unstructured":"Other saturated scaffolds \u20142-oxabicyclo[2.1.1]hexane bicyclo[3.1.1]heptane [2]-ladderane 3-azabicyclo[3.1.1]heptane cuneane \u2014were also recently proposed to mimic themeta-substituted (hetero)aromatic rings in bioactive compounds. 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