Home / Publications / Synthesis of a library of 2-aryl-2H-tetrazole-5-carboxamides for photoaffinity labeling of aminergic G-protein coupled receptors

Synthesis of a library of 2-aryl-2H-tetrazole-5-carboxamides for photoaffinity labeling of aminergic G-protein coupled receptors

Daniil Dmitrievich Zhukovsky 1
Daniil Dmitrievich Zhukovsky
, 
Evgeny Victorovich Kanov 1
Evgeny Victorovich Kanov
, 
Raul Radikovich Gainetdinov 1
Raul Radikovich Gainetdinov
, 
Mikhail Yur'evich Krasavin 1, 2
Mikhail Yur'evich Krasavin
10.1016/j.mencom.2022.09.011
Published 2022-09-05
Communication , Volume 32, Issue 5, 604-605
0
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Zhukovsky D. D. et al. Synthesis of a library of 2-aryl-2H-tetrazole-5-carboxamides for photoaffinity labeling of aminergic G-protein coupled receptors // Mendeleev Communications. 2022. Vol. 32. No. 5. pp. 604-605.
GOST all authors (up to 50) Copy
Zhukovsky D. D., Kanov E. V., Gainetdinov R. R., Krasavin M. Y. Synthesis of a library of 2-aryl-2H-tetrazole-5-carboxamides for photoaffinity labeling of aminergic G-protein coupled receptors // Mendeleev Communications. 2022. Vol. 32. No. 5. pp. 604-605.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2022.09.011
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.09.011
TI - Synthesis of a library of 2-aryl-2H-tetrazole-5-carboxamides for photoaffinity labeling of aminergic G-protein coupled receptors
T2 - Mendeleev Communications
AU - Zhukovsky, Daniil Dmitrievich
AU - Kanov, Evgeny Victorovich
AU - Gainetdinov, Raul Radikovich
AU - Krasavin, Mikhail Yur'evich
PY - 2022
DA - 2022/09/05
PB - Mendeleev Communications
SP - 604-605
IS - 5
VL - 32
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2022_Zhukovsky,
author = {Daniil Dmitrievich Zhukovsky and Evgeny Victorovich Kanov and Raul Radikovich Gainetdinov and Mikhail Yur'evich Krasavin},
title = {Synthesis of a library of 2-aryl-2H-tetrazole-5-carboxamides for photoaffinity labeling of aminergic G-protein coupled receptors},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.09.011},
number = {5},
pages = {604--605},
doi = {10.1016/j.mencom.2022.09.011}
}
MLA
Cite this
MLA Copy
Zhukovsky, Daniil Dmitrievich, et al. “Synthesis of a library of 2-aryl-2H-tetrazole-5-carboxamides for photoaffinity labeling of aminergic G-protein coupled receptors.” Mendeleev Communications, vol. 32, no. 5, Sep. 2022, pp. 604-605. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.09.011.

Keywords

[3+2] cycloaddition
GPCR privileged ligands
photoaffinity labeling
silver(t) catalysis
tetrazoles
α-diazo acetamides

Abstract

A four-step approach to 2-aryl-2H-tetrazole-5-carboxamides bearing GPCR-focused N-substituted piperazine residues involves ‘SAFE’ diazotransfer onto 1-(piperazin-1-yl)butane-1,3-diones followed by [3+2] cycloaddition of arenediazonium cations at the intermediate ααα-diazo acetamides. The compounds prepared are intended for photoaffinity labeling of aminergic G-protein coupled receptors.

References

1.
Know your target, know your molecule
Bunnage M.E., Gilbert A.M., Jones L.H., Hett E.C.
Nature Chemical Biology, 2015
2.
The Mechanism of Photoaffinity Labeling
Ruoho A.E., Kiefer H., Roeder P.E., Singer S.J.
Proceedings of the National Academy of Sciences of the United States of America, 1973
3.
Photoaffinity labeling in target- and binding-site identification
Smith E., Collins I.
Future Medicinal Chemistry, 2015
4.
Nonspecific protein labeling of photoaffinity linkers correlates with their molecular shapes in living cells
Park H., Koo J.Y., Srikanth Y.V., Oh S., Lee J., Park J., Park S.B.
Chemical Communications, 2016
6.
Photoaffinity labelling strategies for mapping the small molecule–protein interactome
Burton N.R., Kim P., Backus K.M.
Organic and Biomolecular Chemistry, 2021
7.
Affinity Labelling of Antibodies with Aryl Nitrene as Reactive Group
FLEET G.W., PORTER R.R., KNOWLES J.R.
Nature, 1969
8.
Aryldiazirines. Potential reagents for photolabeling of biological receptor sites
Smith R.A., Knowles J.R.
Journal of the American Chemical Society, 1973
9.
Photoaffinity labeling of peptide hormone binding sites.
Galardy R.E., Craig L.C., Jamieson J.D., Printz M.P.
Journal of Biological Chemistry, 1974
10.
Process Chemistry in Antiviral Research
Zhong Y., Yasuda N., Li H., McLaughlin M., Tschaen D.
Topics in Current Chemistry, 2016
11.
Evaluation of α-Pyrones and Pyrimidones as Photoaffinity Probes for Affinity-Based Protein Profiling
Battenberg O.A., Nodwell M.B., Sieber S.A.
Journal of Organic Chemistry, 2011
12.
2-Aryl-5-carboxytetrazole as a New Photoaffinity Label for Drug Target Identification
Herner A., Marjanovic J., Lewandowski T.M., Marin V., Patterson M., Miesbauer L., Ready D., Williams J., Vasudevan A., Lin Q.
Journal of the American Chemical Society, 2016
14.
10.1016/j.mencom.2022.09.011_b0070
Levashova
Eur. J. Org. Chem., 2020
15.
Sapegin A.V., Peshkov A.A., Kanov E.V., Gainetdinov R.R., Duszyńska B., Bojarski A.J., Krasavin M.
Mendeleev Communications, 2021
16.
Levashova E., Firsov A., Bakulina O., Peshkov A., Kanov E., Gainetdinov R.R., Krasavin M.
Mendeleev Communications, 2021
17.
Recognition of Privileged Structures by G-Protein Coupled Receptors
Bondensgaard K., Ankersen M., Thøgersen H., Hansen B.S., Wulff B.S., Bywater R.P.
Journal of Medicinal Chemistry, 2004
18.
Privileged structure based ligands for melanocortin-4 receptors—Aliphatic piperazine derivatives
Briner K., Collado I., Fisher M.J., García-Paredes C., Husain S., Kuklish S.L., Mateo A.I., O’Brien T.P., Ornstein P.L., Zgombick J., de Frutos Ó.
Bioorganic and Medicinal Chemistry Letters, 2006
19.
Biophysical Fragment Screening of the β1-Adrenergic Receptor: Identification of High Affinity Arylpiperazine Leads Using Structure-Based Drug Design
Christopher J.A., Brown J., Doré A.S., Errey J.C., Koglin M., Marshall F.H., Myszka D.G., Rich R.L., Tate C.G., Tehan B., Warne T., Congreve M.
Journal of Medicinal Chemistry, 2013
22.
Shevalev R.M., Zhmurov P.A., Dar’in D.V., Krasavin M.
Mendeleev Communications, 2020