Spiro[3.3]heptane as a Saturated Benzene Bioisostere**
Kateryna Prysiazhniuk, Oleksandr Datsenko, Олександр Поліщук, Stanislav Shulha, Oleh Shablykin, Yelyzaveta Nikandrova, Kateryna Horbatok, Iryna Bodenchuk, Petro Borysko, Dmytro Shepilov, Iryna Pishel, Vladimir Kubyshkin, Pavel K. Mykhailiuk
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.
Topics & Concepts
HeptaneBioisostereBenzeneChemistryOrganic chemistryBiochemistryIn vitroChemical synthesisOrganic Chemistry Cycloaddition ReactionsChemical Reaction MechanismsAsymmetric Synthesis and Catalysis