Oxa-spirocycles: synthesis, properties and applications

Kateryna Fominova; Taras Diachuk; Dmitry Granat; Taras Savchuk; Vladyslav Vilchynskyi; Oleksiy Svitlychnyi; Vladyslav Meliantsev; Igor Kovalchuk; Eduard Litskan; Vadym V. Levterov; Valentyn R. Badlo; Ruslan I. Vaskevych; Alla I. Vaskevych; Andrii V. Bolbut; Volodymyr V. Semeno; Rustam Iminov; Kostiantyn Shvydenko; Anastasiia S. Kuznetsova; Yurii V. Dmytriv; Daniil Vysochyn; Vasyl Ripenko; Andrei A. Tolmachev; Olexandra Pavlova; Halyna Kuznietsova; Iryna Pishel; Petro Borysko; Pavel K. Mykhailiuk

doi:10.1039/D1SC03615G

Oxa-spirocycles: synthesis, properties and applications†

Kateryna Fominova,^a Taras Diachuk,^a Dmitry Granat,^a Taras Savchuk,^a Vladyslav Vilchynskyi,

^a Oleksiy Svitlychnyi,^a Vladyslav Meliantsev,^a Igor Kovalchuk,^a Eduard Litskan,^a Vadym V. Levterov,^a Valentyn R. Badlo,^a Ruslan I. Vaskevych,^b Alla I. Vaskevych,^c Andrii V. Bolbut,^b Volodymyr V. Semeno,

^a Rustam Iminov,^a Kostiantyn Shvydenko,^b Anastasiia S. Kuznetsova,^d Yurii V. Dmytriv,^ac Daniil Vysochyn,^a Vasyl Ripenko,^a Andrei A. Tolmachev,^a Olexandra Pavlova,^e Halyna Kuznietsova,

^e Iryna Pishel,

^e Petro Borysko

^e and Pavel K. Mykhailiuk

*^a

Author affiliations

* Corresponding authors

^a Enamine Ltd, Chervonotkatska 78, 02094 Kyiv, Ukraine
E-mail: Pavel.Mykhailiuk@gmail.com
Web: http://www.enamine.net, http://www.mykhailiukchem.org

^b Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska St. 5, 02094 Kyiv, Ukraine

^c National Technical University of Ukraine, Igor Sikorsky Kiev Polytechnic Institute, Prosp. Peremohy 37, 03056 Kyiv, Ukraine

^d National Research Tomsk Polytechnic University, Lenin Ave. 30, 634050 Tomsk, Russia

^e Bienta, Chervonotkatska 78, 02094 Kyiv, Ukraine
Web: http://www.bienta.net

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.

Chemical Science

Oxa-spirocycles: synthesis, properties and applications†

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