| Title: |
1‐Azaspiro[3.3]heptane as a Bioisostere of Piperidine** |
| Authors: |
Kirichok, Alexander A.; Tkachuk, Hennadii; Kozyriev, Yevhenii; Shablykin, Oleh; Datsenko, Oleksandr; Granat, Dmitry; Yegorova, Tetyana; Bas, Yuliya P.; Semirenko, Vitalii; Pishel, Iryna; Kubyshkin, Vladimir; Lesyk, Dmytro; Klymenko‐Ulianov, Oleksii; Mykhailiuk, Pavel K. |
| Contributors: |
HORIZON EUROPE European Research Council |
| Source: |
Angewandte Chemie International Edition ; volume 62, issue 51 ; ISSN 1433-7851 1521-3773 |
| Publisher Information: |
Wiley |
| Publication Year: |
2023 |
| Collection: |
Wiley Online Library (Open Access Articles via Crossref) |
| Description: |
1‐Azaspiro[3.3]heptanes were synthesized, characterized, and validated biologically as bioisosteres of piperidine. The key synthesis step was thermal [2+2] cycloaddition between endocyclic alkenes and the Graf isocyanate, ClO 2 S−NCO, to give spirocyclic β‐lactams. Reduction of the β‐lactam ring with alane produced 1‐azaspiro[3.3]heptanes. Incorporation of this core into the anesthetic drug bupivacaine instead of the piperidine fragment resulted in a new patent‐free analogue with high activity. |
| Document Type: |
article in journal/newspaper |
| Language: |
English |
| DOI: |
10.1002/anie.202311583 |
| Availability: |
https://doi.org/10.1002/anie.202311583; https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.202311583 |
| Rights: |
http://creativecommons.org/licenses/by-nc/4.0/ |
| Accession Number: |
edsbas.7D2AC302 |
| Database: |
BASE |