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Spiro[3.3]heptane as a Saturated Benzene Bioisostere** |
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| Authors: | Kateryna Prysiazhniuk Oleksandr P. Datsenko Oleksandr Polishchuk Stanislav Shulha Oleh Shablykin Yelyzaveta Nikandrova Kateryna Horbatok Iryna Bodenchuk Petro Borysko Dmytro Shepilov Iryna Pishel Vladimir Kubyshkin Pavel K. Mykhailiuk |
| Affiliation: | 1. Enamine Ltd., Winston Churchill Str. 78, 02094 Kyiv, Ukraine;2. Enamine Ltd., Winston Churchill Str. 78, 02094 Kyiv, Ukraine V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry NAS of Ukraine, 02094 Kyiv, Ukraine;3. Bienta, Winston Churchill Str. 78, 02094 Kyiv, Ukraine |
| Abstract: | The spiro[3.3]heptane core, with the non-coplanar exit vectors, was shown to be a saturated benzene bioisostere. This scaffold was incorporated into the anticancer drug sonidegib (instead of the meta-benzene), the anticancer drug vorinostat (instead of the phenyl ring), and the anesthetic drug benzocaine (instead of the para-benzene). The patent-free saturated analogs obtained showed a high potency in the corresponding biological assays. |
| Keywords: | Bioisostere Cyclobutane Medicinal Chemistry Spiro[3.3]Heptane Spirocycles |