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Oxa-spirocycles: synthesis, properties and applications.

ABSTRACT: 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.

SUBMITTER: Fominova K

PROVIDER: S-EPMC8447932 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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Oxa-spirocycles: synthesis, properties and applications.

Fominova Kateryna K Diachuk Taras T Granat Dmitry D Savchuk Taras T Vilchynskyi Vladyslav V Svitlychnyi Oleksiy O Meliantsev Vladyslav V Kovalchuk Igor I Litskan Eduard E Levterov Vadym V VV Badlo Valentyn R VR Vaskevych Ruslan I RI Vaskevych Alla I AI Bolbut Andrii V AV Semeno Volodymyr V VV Iminov Rustam R Shvydenko Kostiantyn K Kuznetsova Anastasiia S AS Dmytriv Yurii V YV Vysochyn Daniil D Ripenko Vasyl V Tolmachev Andrei A AA Pavlova Olexandra O Kuznietsova Halyna H Pishel Iryna I Borysko Petro P Mykhailiuk Pavel K PK

Chemical science 20210727 34

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 <i>in vivo</i>. ...[more]

PMID: 34667540

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