Home / Publications / Microwave-assisted synthesis of 5-aryl-3-hydroxy-2-oxindole derivatives and evaluation of their antiglaucomic activity

Microwave-assisted synthesis of 5-aryl-3-hydroxy-2-oxindole derivatives and evaluation of their antiglaucomic activity

Alexander Mikhailovich Efremov 1, 2
Alexander Mikhailovich Efremov
, 
Denis Aleksandrovich Babkov 3
Denis Aleksandrovich Babkov
, 
Olga Valer'evna Beznos 4
Olga Valer'evna Beznos
, 
Elena Vyacheslavovna Sokolova 3
Elena Vyacheslavovna Sokolova
, 
Alexander Alekseevich Spasov 3
Alexander Alekseevich Spasov
, 
Vladimir Nikolaevich Ivanov 2
Vladimir Nikolaevich Ivanov
, 
Alexander Vital'evich Kurkin 2
Alexander Vital'evich Kurkin
, 
Natalia Borisovna Chesnokova 4
Natalia Borisovna Chesnokova
, 
Natalia Alexandrovna Lozinskaya 2
Natalia Alexandrovna Lozinskaya
1 Institute of Physiologically Active Compounds, Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, Chernogolovka, Moscow Region, Russian Federation
2 Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
3 Volgograd State Medical University, Volgograd, Russian Federation
4 Helmholtz National Medical Centre of Eye Diseases, Moscow, Russian Federation
10.1016/j.mencom.2023.06.035
Published 2023-06-13
Communication , Volume 33, Issue 4, 550-552
6
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Efremov A. M. et al. Microwave-assisted synthesis of 5-aryl-3-hydroxy-2-oxindole derivatives and evaluation of their antiglaucomic activity // Mendeleev Communications. 2023. Vol. 33. No. 4. pp. 550-552.
GOST all authors (up to 50) Copy
Efremov A. M., Babkov D. A., Beznos O. V., Sokolova E. V., Spasov A. A., Ivanov V. N., Kurkin A. V., Chesnokova N. B., Lozinskaya N. A. Microwave-assisted synthesis of 5-aryl-3-hydroxy-2-oxindole derivatives and evaluation of their antiglaucomic activity // Mendeleev Communications. 2023. Vol. 33. No. 4. pp. 550-552.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2023.06.035
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.06.035
TI - Microwave-assisted synthesis of 5-aryl-3-hydroxy-2-oxindole derivatives and evaluation of their antiglaucomic activity
T2 - Mendeleev Communications
AU - Efremov, Alexander Mikhailovich
AU - Babkov, Denis Aleksandrovich
AU - Beznos, Olga Valer'evna
AU - Sokolova, Elena Vyacheslavovna
AU - Spasov, Alexander Alekseevich
AU - Ivanov, Vladimir Nikolaevich
AU - Kurkin, Alexander Vital'evich
AU - Chesnokova, Natalia Borisovna
AU - Lozinskaya, Natalia Alexandrovna
PY - 2023
DA - 2023/06/13
PB - Mendeleev Communications
SP - 550-552
IS - 4
VL - 33
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2023_Efremov,
author = {Alexander Mikhailovich Efremov and Denis Aleksandrovich Babkov and Olga Valer'evna Beznos and Elena Vyacheslavovna Sokolova and Alexander Alekseevich Spasov and Vladimir Nikolaevich Ivanov and Alexander Vital'evich Kurkin and Natalia Borisovna Chesnokova and Natalia Alexandrovna Lozinskaya},
title = {Microwave-assisted synthesis of 5-aryl-3-hydroxy-2-oxindole derivatives and evaluation of their antiglaucomic activity},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.06.035},
number = {4},
pages = {550--552},
doi = {10.1016/j.mencom.2023.06.035}
}
MLA
Cite this
MLA Copy
Efremov, Alexander Mikhailovich, et al. “Microwave-assisted synthesis of 5-aryl-3-hydroxy-2-oxindole derivatives and evaluation of their antiglaucomic activity.” Mendeleev Communications, vol. 33, no. 4, Jun. 2023, pp. 550-552. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.06.035.

Keywords

antiglaucomic
condensation.
indolin-2-one
intraocular pressure
microwave irradiation
NRH:quinone oxidoreductase 2 inhibitors
oxindole

Abstract

A set of new 5-aryl-3-hydroxy-2-oxindoles was synthesized by decarboxylative condensation of the corresponding 5-aryl-substituted isatins with malonic or cyanoacetic acids under microwave irradiation. The antiglaucomic activity of the obtained compounds was evaluated. The most water soluble compounds can reduce the intraocular pressure (IOP) up to 2 Torr.

References

.
Barashkin A.A., Polyakov V.S., Shikut N.L., Putilova A.D., Gorovoy A.R., Degtiarev A.D., Tafeenko V.A., Tarasevich B.N., Zyk N.V., Beloglazkina E.K.
Mendeleev Communications, 2022
.
Synthesis of novel МТ3 receptor ligands via an unusual Knoevenagel condensation.
Volkova M.S., Jensen K.C., Lozinskaya N.A., Sosonyuk S.E., Proskurnina M.V., Mesecar A.D., Zefirov N.S.
Bioorganic and Medicinal Chemistry Letters, 2012
.
Novel agonists of melatonin receptors as promising hypotensive and neuroprotective agents for therapy of glaucoma
Chesnokova N.B., Beznos O.V., Lozinskaya N.A., Volkova M.S., Zaryanova E.V., Zefirov N.S., Grigoryev A.V.
Biochemistry (Moscow) Supplement Series B: Biomedical Chemistry, 2017
.
Ocular ??-Blockers in Glaucoma Management
Brooks A.M., Gillies W.E.
Drugs and Aging, 1992
.
Topical carbonic anhydrase inhibitors and glaucoma in 2021: where do we stand?
Stoner A., Harris A., Oddone F., Belamkar A., Verticchio Vercellin A.C., Shin J., Januleviciene I., Siesky B.
British Journal of Ophthalmology, 2021
.
Synthesis of New 2,3-Dihydroindole Derivatives and Evaluation of Their Melatonin Receptor Binding Affinity
Volkova M.S., Efremov A.M., Bezsonova E.N., Tsymliakov M.D., Maksutova A.I., Salykina M.A., Sosonyuk S.E., Shevtsova E.F., Lozinskaya N.A.
Molecules, 2022
.
Identification of the Melatonin-binding SiteMT 3 as the Quinone Reductase 2*
Nosjean O., Ferro M., Cogé F., Beauverger P., Henlin J., Lefoulon F., Fauchère J., Delagrange P., Canet E., Boutin J.A.
Journal of Biological Chemistry, 2000
.
Protective effects of melatonin in experimental free radical-related ocular diseases
Siu A.W., Maldonado M., Sanchez-Hidalgo M., Tan D., Reiter R.J.
Journal of Pineal Research, 2006
.
Update on the role of alpha-agonists in glaucoma management
Arthur S., Cantor L.B.
Experimental Eye Research, 2011
.
Ophthalmic formulations of the intraocular hypotensive melatonin agent 5-MCA-NAT
Andrés-Guerrero V., Alarma-Estrany P., Molina-Martínez I.T., Peral A., Herrero-Vanrell R., Pintor J.
Experimental Eye Research, 2009
.
Switching within glaucoma medication class
Law S.K.
Current Opinion in Ophthalmology, 2009
.
Microwave-Assisted Synthesis of 3-Hydroxy-2-oxindoles and Pilot Evaluation of Their Antiglaucomic Activity
Efremov A.M., Beznos O.V., Eremeev R.O., Chesnokova N.B., Milaeva E.R., Shevtsova E.F., Lozinskaya N.A.
International Journal of Molecular Sciences, 2023
.
Het(aryl)isatin to het(aryl)aminoindoline scaffold hopping: A route to selective inhibitors of matrix metalloproteinases
Ivanov V.N., Agamennone M., Iusupov I.R., Laghezza A., Novoselov A.M., Manasova E.V., Altieri A., Tortorella P., Shtil A.A., Kurkin A.V.
Arabian Journal of Chemistry, 2022