Oxa-spirocycles: synthesis, properties and applications.
Kateryna FominovaTaras DiachukDmitry GranatTaras SavchukVladyslav VilchynskyiOleksiy SvitlychnyiVladyslav MeliantsevIgor KovalchukEduard LitskanVadym V LevterovValentyn R BadloRuslan I VaskevychAlla I VaskevychAndrii V BolbutVolodymyr V SemenoRustam IminovKostiantyn ShvydenkoAnastasiia S KuznetsovaYurii V DmytrivDaniil VysochynVasyl RipenkoAndrei A TolmachevOlexandra PavlovaHalyna M KuznietsovaIryna PishelPetro O BoryskoPavel K MykhailiukPublished in: Chemical science (2021)
A general approach to a new generation of spirocyclic molecules - oxa-spirocycles - was developed. The key synthetic step was iodocyclization. More than 150 oxa-spirocyclic compounds were prepared. Incorporation of an oxygen atom into the spirocyclic unit dramatically improved water solubility (by up to 40 times) and lowered lipophilicity. More potent oxa-spirocyclic analogues of antihypertensive drug terazosin were synthesized and studied in vivo.