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(E)-3-Arylidene-4-diazopyrrolidine-2,5-diones conveniently elaborated into cytotoxic compounds bearing primary sulfonamide and Michael acceptor moieties

Polina Sergeevna Paramonova 1
Polina Sergeevna Paramonova
, 
Tatiana Valeryevna Sharonova 1
Tatiana Valeryevna Sharonova
, 
Stanislav Alekseevich Kalinin 1, 2
Stanislav Alekseevich Kalinin
, 
Evgeny Gennadievich Chupakhin 1, 3
Evgeny Gennadievich Chupakhin
, 
Alexander Siyasatovich Bunev 2
Alexander Siyasatovich Bunev
, 
Mikhail Yur'evich Krasavin 1, 3
Mikhail Yur'evich Krasavin
10.1016/j.mencom.2022.03.007
Published 2022-03-06
Communication , Volume 32, Issue 2, 176-177
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Paramonova P. S. et al. (E)-3-Arylidene-4-diazopyrrolidine-2,5-diones conveniently elaborated into cytotoxic compounds bearing primary sulfonamide and Michael acceptor moieties // Mendeleev Communications. 2022. Vol. 32. No. 2. pp. 176-177.
GOST all authors (up to 50) Copy
Paramonova P. S., Sharonova T. V., Kalinin S. A., Chupakhin E. G., Bunev A. S., Krasavin M. Y. (E)-3-Arylidene-4-diazopyrrolidine-2,5-diones conveniently elaborated into cytotoxic compounds bearing primary sulfonamide and Michael acceptor moieties // Mendeleev Communications. 2022. Vol. 32. No. 2. pp. 176-177.
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TY - JOUR
DO - 10.1016/j.mencom.2022.03.007
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.007
TI - (E)-3-Arylidene-4-diazopyrrolidine-2,5-diones conveniently elaborated into cytotoxic compounds bearing primary sulfonamide and Michael acceptor moieties
T2 - Mendeleev Communications
AU - Paramonova, Polina Sergeevna
AU - Sharonova, Tatiana Valeryevna
AU - Kalinin, Stanislav Alekseevich
AU - Chupakhin, Evgeny Gennadievich
AU - Bunev, Alexander Siyasatovich
AU - Krasavin, Mikhail Yur'evich
PY - 2022
DA - 2022/03/06
PB - Mendeleev Communications
SP - 176-177
IS - 2
VL - 32
ER -
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@article{2022_Paramonova,
author = {Polina Sergeevna Paramonova and Tatiana Valeryevna Sharonova and Stanislav Alekseevich Kalinin and Evgeny Gennadievich Chupakhin and Alexander Siyasatovich Bunev and Mikhail Yur'evich Krasavin},
title = {(E)-3-Arylidene-4-diazopyrrolidine-2,5-diones conveniently elaborated into cytotoxic compounds bearing primary sulfonamide and Michael acceptor moieties},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.007},
number = {2},
pages = {176--177},
doi = {10.1016/j.mencom.2022.03.007}
}
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Paramonova, Polina Sergeevna, et al. “(E)-3-Arylidene-4-diazopyrrolidine-2,5-diones conveniently elaborated into cytotoxic compounds bearing primary sulfonamide and Michael acceptor moieties.” Mendeleev Communications, vol. 32, no. 2, Mar. 2022, pp. 176-177. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.007.

Keywords

Anti-proliferative agents
Cell viability
Diazo coupling
Enzyme inhibitors
Michael acceptors
MTT assay
Rhodium catalysis
sulfonamides

Abstract

The earlier described (E)-3-arylidene-4-diazopyrrolidine-2,5-diones have been elaborated into two distinct series of compounds both bearing a primary sulfonamide moiety and an electrophilic ‘Michael acceptor’ motif. These compounds demonstrated cytotoxicity against colorectal cancer cell line HCT 116.

References

1.
Insertion of metal carbenes into the anilinic N-H bond of unprotected aminobenzenesulfonamides delivers low nanomolar inhibitors of human carbonic anhydrase IX and XII isoforms.
Sharonova T., Paramonova P., Kalinin S., Bunev A., Gasanov R.Е., Nocentini A., Sharoyko V., Tennikova T.B., Dar’in D., Supuran C.T., Krasavin M.
European Journal of Medicinal Chemistry, 2021
2.
Chupakhin E.G., Kantin G.P., Dar’in D.V., Krasavin M.
Mendeleev Communications, 2021
6.
Carbonic Anhydrases: Role in pH Control and Cancer
Mboge M., Mahon B., McKenna R., Frost S.
Metabolites, 2018
7.
Identification of Michael acceptor-centric pharmacophores with substituents that yield strong thioredoxin reductase inhibitory character correlated to antiproliferative activity.
Gan F., Kaminska K.K., Yang H., Liew C., Leow P., So C., Tu L.N., Roy A., Yap C., Kang T., Chui W., Chew E.
Antioxidants and Redox Signaling, 2013
8.
Indolin-2-one compounds targeting thioredoxin reductase as potential anticancer drug leads
Kaminska K.K., Bertrand H.C., Tajima H., Stafford W.C., Cheng Q., Chen W., Wells G., Arner E.S., Chew E.
Oncotarget, 2016
9.
Combining carbonic anhydrase and thioredoxin reductase inhibitory motifs within a single molecule dramatically increases its cytotoxicity
Krasavin M., Sharonova T., Sharoyko V., Zhukovsky D., Kalinin S., Žalubovskis R., Tennikova T., Supuran C.T.
Journal of Enzyme Inhibition and Medicinal Chemistry, 2020
10.
Characterization of HCT116 human colon cancer cells in an orthotopic model.
Rajput A., Dominguez San Martin I., Rose R., Beko A., LeVea C., Sharratt E., Mazurchuk R., Hoffman R.M., Brattain M.G., Wang J.
Journal of Surgical Research, 2008