Wiley
Angewandte Chemie
,  volume 135 ,  issue 51

1‐Azaspiro[3.3]heptane as a Bioisostere of Piperidine

Alexander A. Kirichok 1, 2
, 
Hennadii Tkachuk 1
, 
Yevhenii Kozyriev 1, 3
, 
Oleh Shablykin 1, 4
, 
Oleksandr Datsenko 1
, 
Dmitry Granat 1
, 
Tetyana Yegorova 2
, 
Yuliya P Bas 2
, 
Vitalii Semirenko 1
, 
Iryna Pishel 1
, 
Vladimir Kubyshkin 1
, 
Dmytro Lesyk 5
, 
Oleksii Klymenko-Ulianov 5
, 
Pavel K. Mykhailiuk 1, 2
1
 
Enamine Ltd Winston Churchill Str. 78 02094 Kyiv Ukraine | 
2
 
Taras Shevchenko National University of Kyiv Faculty of Chemistry Volodymyrska 60 01601 Kyiv Ukraine | 
3
 
Oles Honchar Dnipro National University Faculty of Chemistry 72 Gagarina Ave. 49010 Dnipro Ukraine | 
4
 
V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine Akademika Kukharya 1 02094 Kyiv Ukraine | 
5
 
Bienta Winston Churchill Str. 78 02094 Kyiv Ukraine | 
Publication type: Journal Article
Publication date: 2023-11-14
Wiley
SJR: —
CiteScore: —
Impact factor: —
ISSN: 00448249, 15213757
General Medicine
Abstract

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, ClO2S−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.

Found 
Found 

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Kirichok A. A. et al. 1‐Azaspiro[3.3]heptane as a Bioisostere of Piperidine // Angewandte Chemie. 2023. Vol. 135. No. 51.
GOST all authors (up to 50) Copy
Kirichok A. A., Tkachuk H., Kozyriev Y., Shablykin O., Datsenko O., Granat D., Yegorova T., Bas Y. P., Semirenko V., Pishel I., Kubyshkin V., Lesyk D., Klymenko-Ulianov O., Mykhailiuk P. K. 1‐Azaspiro[3.3]heptane as a Bioisostere of Piperidine // Angewandte Chemie. 2023. Vol. 135. No. 51.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1002/ange.202311583
UR - https://doi.org/10.1002/ange.202311583
TI - 1‐Azaspiro[3.3]heptane as a Bioisostere of Piperidine
T2 - Angewandte Chemie
AU - Kirichok, Alexander A.
AU - Tkachuk, Hennadii
AU - Kozyriev, Yevhenii
AU - Shablykin, Oleh
AU - Datsenko, Oleksandr
AU - Granat, Dmitry
AU - Yegorova, Tetyana
AU - Bas, Yuliya P
AU - Semirenko, Vitalii
AU - Pishel, Iryna
AU - Kubyshkin, Vladimir
AU - Lesyk, Dmytro
AU - Klymenko-Ulianov, Oleksii
AU - Mykhailiuk, Pavel K.
PY - 2023
DA - 2023/11/14
PB - Wiley
IS - 51
VL - 135
SN - 0044-8249
SN - 1521-3757
ER -
BibTex
Cite this
BibTex (up to 50 authors) Copy
@article{2023_Kirichok,
author = {Alexander A. Kirichok and Hennadii Tkachuk and Yevhenii Kozyriev and Oleh Shablykin and Oleksandr Datsenko and Dmitry Granat and Tetyana Yegorova and Yuliya P Bas and Vitalii Semirenko and Iryna Pishel and Vladimir Kubyshkin and Dmytro Lesyk and Oleksii Klymenko-Ulianov and Pavel K. Mykhailiuk},
title = {1‐Azaspiro[3.3]heptane as a Bioisostere of Piperidine},
journal = {Angewandte Chemie},
year = {2023},
volume = {135},
publisher = {Wiley},
month = {nov},
url = {https://doi.org/10.1002/ange.202311583},
number = {51},
doi = {10.1002/ange.202311583}
}