Spiro3.3heptane as a Saturated Benzene Bioisostere

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 benzo...

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Published in:Angewandte Chemie International Edition 2024-02, Vol.63 (9), p.e202316557
Main Authors: Prysiazhniuk, Kateryna, Datsenko, Oleksandr P, Polishchuk, Oleksandr, Shulha, Stanislav, Shablykin, Oleh, Nikandrova, Yelyzaveta, Horbatok, Kateryna, Bodenchuk, Iryna, Borysko, Petro, Shepilov, Dmytro, Pishel, Iryna, Kubyshkin, Vladimir, Mykhailiuk, Pavel K
Format: Article
Language:English
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Summary: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.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.
ISSN:1521-3773
1521-3773
DOI:10.1002/anie.202316557