Spiro[3.3]heptane as a Saturated Benzene Bioisostere.

Autor: Prysiazhniuk K; Enamine Ltd., Winston Churchill Str. 78, 02094, Kyiv, Ukraine., Datsenko OP; Enamine Ltd., Winston Churchill Str. 78, 02094, Kyiv, Ukraine., Polishchuk O; Enamine Ltd., Winston Churchill Str. 78, 02094, Kyiv, Ukraine., Shulha S; Enamine Ltd., Winston Churchill Str. 78, 02094, Kyiv, Ukraine., Shablykin O; Enamine Ltd., Winston Churchill Str. 78, 02094, Kyiv, Ukraine.; V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry NAS of Ukraine, 02094, Kyiv, Ukraine., Nikandrova Y; Bienta, Winston Churchill Str. 78, 02094, Kyiv, Ukraine., Horbatok K; Bienta, Winston Churchill Str. 78, 02094, Kyiv, Ukraine., Bodenchuk I; Bienta, Winston Churchill Str. 78, 02094, Kyiv, Ukraine., Borysko P; Bienta, Winston Churchill Str. 78, 02094, Kyiv, Ukraine., Shepilov D; Bienta, Winston Churchill Str. 78, 02094, Kyiv, Ukraine., Pishel I; Bienta, Winston Churchill Str. 78, 02094, Kyiv, Ukraine., Kubyshkin V; Enamine Ltd., Winston Churchill Str. 78, 02094, Kyiv, Ukraine., Mykhailiuk PK; Enamine Ltd., Winston Churchill Str. 78, 02094, Kyiv, Ukraine.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Feb 26; Vol. 63 (9), pp. e202316557. Date of Electronic Publication: 2024 Jan 22.
DOI: 10.1002/anie.202316557
Abstrakt: 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.
(© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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