In vivo- and in silico-driven identification of novel synthetic quinoxalines as anticonvulsants and AMPA inhibitors.
Animals
Anticonvulsants
/ chemical synthesis
Dose-Response Relationship, Drug
Injections, Intraperitoneal
Male
Mice
Molecular Docking Simulation
Molecular Structure
Pentylenetetrazole
Quinoxalines
/ chemical synthesis
Seizures
/ chemically induced
Structure-Activity Relationship
alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid
/ administration & dosage
AMPA antagonists
anticonvulsant
in silico studies
molecular docking
pharmacokinetic
quinoxalines
Journal
Archiv der Pharmazie
ISSN: 1521-4184
Titre abrégé: Arch Pharm (Weinheim)
Pays: Germany
ID NLM: 0330167
Informations de publication
Date de publication:
May 2021
May 2021
Historique:
revised:
04
01
2021
received:
30
11
2020
accepted:
15
01
2021
pubmed:
10
2
2021
medline:
4
11
2021
entrez:
9
2
2021
Statut:
ppublish
Résumé
The lack of effective therapies for epileptic patients and the potentially harmful consequences of untreated seizure incidents have made epileptic disorders in humans a major health concern. Therefore, new and more potent anticonvulsant drugs are continually sought after, to combat epilepsy. On the basis of the pharmacophoric structural specifications of effective α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) antagonists with an efficient anticonvulsant activity, the present work reports the design and synthesis of two novel sets of quinoxaline derivatives. The anticonvulsant activity of the synthesized compounds was evaluated in vivo according to the pentylenetetrazol-induced seizure protocol, and the results were compared with those of perampanel as a reference drug. Among the synthesized compounds, 24, 28, 32, and 33 showed promising activities with ED
Identifiants
pubmed: 33559320
doi: 10.1002/ardp.202000449
doi:
Substances chimiques
Anticonvulsants
0
Quinoxalines
0
alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid
77521-29-0
Pentylenetetrazole
WM5Z385K7T
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2000449Informations de copyright
© 2021 Deutsche Pharmazeutische Gesellschaft.
Références
J. X. Wang, M. W. Irvine, E. S. Burnell, K. Sapkota, R. J. Thatcher, M. Li, N. Simorowski, A. Volianskis, G. L. Collingridge, D. T. Monaghan, D. E. Jane, H. Furukawa, Nat. Commun. 2020, 11, 423. https://doi.org/10.1038/s41467-020-14321-0
The World Health Organization, Epilepsy, 2020. https://www.who.int/health-topics/epilepsy#tab=tab_1 (accessed: October 15).
M. A. Rogawski, Epilepsy Curr. 2011, 11, 56. https://doi.org/10.5698/1535-7511-11.2.56
M. A. Rogawski, W. Löscher, J. M. Rho, Cold Spring Harbor Perspect. Med. 2016, 6, a022780. https://doi.org/10.1101/cshperspect.a022780
H. Abul-Khair, S. Elmeligie, A. Bayoumi, A. Ghiaty, A. El-Morsy, M. H. Hassan, J. Heterocycl. Chem. 2013, 50, 1202. https://doi.org/10.1002/jhet.714
A. A. El-Helby, R. R. A. Ayyad, M. F. Zayed, H. S. Abulkhair, H. Elkady, K. El-Adl, Arch. Pharm. (Weinheim) 2019, 352, 1800387. https://doi.org/10.1002/ardp.201800387
A.-G. A. El-Helby, R. R. A. Ayyad, K. El-Adl, H. Sakr, A. A. Abd-Elrahman, I. H. Eissa, A. Elwan, Med. Chem. Res. 2016, 25, 3030. https://doi.org/10.1007/s00044-016-1723-7
J. A. McCauley, C. R. Theberge, J. J. Romano, S. B. Billings, K. D. Anderson, D. A. Claremon, R. M. Freidinger, R. A. Bednar, S. D. Mosser, S. L. Gaul, T. M. Connolly, C. L. Condra, M. Xia, M. E. Cunningham, B. Bednar, G. L. Stump, J. J. Lynch, A. Macaulay, K. A. Wafford, K. S. Koblan, N. J. Liverton, J. Med. Chem. 2004, 47, 2089. https://doi.org/10.1021/jm030483s
T. Fuchigami, H. Yamaguchi, M. Ogawa, L. Biao, M. Nakayama, M. Haratake, Y. Magata, Bioorg. Med. Chem. 2010, 18, 7497. https://doi.org/10.1016/j.bmc.2010.08.053
J. Greenwood, J. Valdes, Pharm. Ther. 2016, 41, 683. http://www.ncbi.nlm.nih.gov/pubmed/27904300
T. Hanada, Biomolecules 2020, 10, 464. https://doi.org/10.3390/biom10030464
F. Rugg-Gunn, Epilepsia 2014, 55, 13. https://doi.org/10.1111/epi.12504
D. Catarzi, V. Colotta, F. Varano, F. R. Calabri, G. Filacchioni, A. Galli, C. Costagli, V. Carlà, J. Med. Chem. 2004, 47, 262. https://doi.org/10.1021/jm030906q
S. Tariq, O. Alam, M. Amir, Arch. Pharm. (Weinheim) 2018, 351, 1700304. https://doi.org/10.1002/ardp.201700304
B. Kaproń, J. J. Łuszczki, A. Siwek, T. Karcz, G. Nowak, M. Zagaja, M. Andres-Mach, A. Stasiłowicz, J. Cielecka-Piontek, J. Kocki, T. Plech, Bioorg. Chem. 2020, 94, 103355. https://doi.org/10.1016/j.bioorg.2019.103355
M. Kessler, M. Baudry, G. Lynch, Brain Res. 1989, 489, 377. https://doi.org/10.1016/0006-8993(89)90875-5
S. Brickley, M. Farrant, G. Swanson, S. Cull-Candy, Neuropharmacology 2001, 41, 730. https://doi.org/10.1016/S0028-3908(01)00135-6
M.-X. Song, X.-Q. Deng, J. Enzyme Inhib. Med. Chem. 2018, 33, 453. https://doi.org/10.1080/14756366.2017.1423068
A. Kebriaeezadeh, S. Emami, M. Ebrahimi, M. Sharifzadeh, R. Khorasani, Biomed. Pharmacother. 2008, 62, 208. https://doi.org/10.1016/j.biopha.2007.12.003
H.-J. Lankau, K. Unverferth, C. Grunwald, H. Hartenhauer, K. Heinecke, K. Bernöster, R. Dost, U. Egerland, C. Rundfeldt, Eur. J. Med. Chem. 2007, 42, 873. https://doi.org/10.1016/j.ejmech.2006.12.022
S. Sari, F. B. Kaynak, S. Dalkara, Pharmacol. Rep. 2018, 70, 1116. https://doi.org/10.1016/j.pharep.2018.06.007
B. A. Vega Alanis, M. T. Iorio, L. L. Silva, K. Bampali, M. Ernst, M. Schnürch, M. D. Mihovilovic, Molecules 2020, 25, 999. https://doi.org/10.3390/molecules25040999
V. B. Makane, E. Vamshi Krishna, U. B. Karale, D. A. Babar, S. Kalari, E. M. Rekha, M. Shukla, G. Kaul, D. Sriram, S. Chopra, S. Misra, H. B. Rode, Arch. Pharm. (Weinheim) 2020, 353, 2000192. https://doi.org/10.1002/ardp.202000192
H. G. Ezzat, A. H. Bayoumi, F. F. Sherbiny, A. M. El-Morsy, A. Ghiaty, M. Alswah, H. S. Abulkhair, Mol. Divers. 2020. https://doi.org/10.1007/s11030-020-10070-w
P. B. Wingrove, K. A. Wafford, C. Bain, P. J. Whiting, Proc. Natl. Acad. Sci. U. S. A. 1994, 91, 4569. https://doi.org/10.1073/pnas.91.10.4569
F. Azam, I. M. Abugrain, M. H. Sanalla, R. F. Elnaas, I. Rajab, Bioinformation 2013, 9, 864. https://doi.org/10.6026/97320630009864
F. Calabri, V. Colotta, D. Catarzi, F. Varano, O. Lenzi, G. Filacchioni, C. Costagli, A. Galli, Eur. J. Med. Chem. 2005, 40, 897. https://doi.org/10.1016/j.ejmech.2005.03.017
S. Wagle, A. V. Adhikari, N. S. Kumari, Eur. J. Med. Chem. 2009, 44, 1135. https://doi.org/10.1016/j.ejmech.2008.06.006.10.1016/j.ejmech.2008.06.006.
J. J. Łuszczki, Pharmacol. Rep. 2009, 61, 197. https://doi.org/10.1016/S1734-1140(09)70024-6
N. Hen, M. Bialer, B. Wlodarczyk, R. H. Finnell, B. Yagen, J. Med. Chem. 2010, 53, 4177. https://doi.org/10.1021/jm100170w
M. Góra, A. Czopek, A. Rapacz, A. Dziubina, M. Głuch-Lutwin, B. Mordyl, J. Obniska, Int. J. Mol. Sci. 2020, 21, 5750. https://doi.org/10.3390/ijms21165750
K. Kamiński, B. Wiklik, J. Obniska, Med. Chem. Res. 2015, 24, 3047. https://doi.org/10.1007/s00044-015-1360-6
A.-G. A. El-Helby, R. R. A. Ayyad, K. El-Adl, H. Elkady, Mol. Divers. 2019, 23, 283. https://doi.org/10.1007/s11030-018-9871-y
M. Alswah, A. Ghiaty, A. El-Morsy, K. El-Gamal, ISRN Org. Chem. 2013, 2013, 1. https://doi.org/10.1155/2013/587054
J. Dudash, Y. Zhang, J. B. Moore, R. Look, Y. Liang, M. P. Beavers, B. R. Conway, P. J. Rybczynski, K. T. Demarest, Bioorg. Med. Chem. Lett. 2005, 15, 4790. https://doi.org/10.1016/j.bmcl.2005.07.021
S. Ihmaid, H. E. A. Ahmed, A. Al-Sheikh Ali, Y. E. Sherif, H. M. Tarazi, S. M. Riyadh, M. F. Zayed, H. S. Abulkhair, H. S. Rateb, Bioorg. Chem. 2017, 72, 234. https://doi.org/10.1016/j.bioorg.2017.04.014
A. M. Omar, S. Ihmaid, E.-S. S. E. Habib, S. S. Althagfan, S. Ahmed, H. S. Abulkhair, H. E. A. Ahmed, Bioorg. Chem. 2020, 99, 103781. https://doi.org/10.1016/j.bioorg.2020.103781
S.-K. Lin, Molecules 1996, 1, 37. https://mdpi.org/lin/quinoxaline.pdf
A. M. El-Morsy, M. S. El-Sayed, H. S. Abulkhair, Open J. Med. Chem. 2017, 07, 1. https://doi.org/10.4236/ojmc.2017.71001
M. H. El-Shershaby, K. M. El-Gamal, A. H. Bayoumi, K. El-Adl, H. E. A. Ahmed, H. S. Abulkhair, Arch. der Pharm. 2020, https://doi.org/10.1002/ardp.202000277
A. Turky, A. H. Bayoumi, F. F. Sherbiny, K. El-Adl, H. S. Abulkhair, Mol. Divers. 2020, https://doi.org/10.1007/s11030-020-10131-0
A. Turky, F. F. Sherbiny, A. Bayoumi, H. E. A. Ahmed, H. S. Abulkhair, Arch. Pharm. (Weinheim) 2020, 353, e2000170. https://doi.org/10.1002/ardp.202000170
H. S. Abulkhair, A. Turky, A. Ghiaty, H. E. A. Ahmed, A. H. Bayoumi, Bioorg. Chem. 2020, 100, 103899. https://doi.org/10.1016/j.bioorg.2020.103899
A. Turky, A. H. Bayoumi, A. Ghiaty, A. S. El-Azab, A. A.-M. Abdel-Aziz, H. S. Abulkhair, Bioorg. Chem. 2020, 101, 104019. https://doi.org/10.1016/j.bioorg.2020.104019
M. H. Hannoun, M. Hagras, A. Kotb, A.-A. M. M. El-Attar, H. S. Abulkhair, Bioorg. Chem. 2020, 94, 103364. https://doi.org/10.1016/j.bioorg.2019.103364
A. A. Gaber, A. H. Bayoumi, A. M. El-morsy, F. F. Sherbiny, A. B. M. Mehany, I. H. Eissa, Bioorg. Chem. 2018, 80, 375. https://doi.org/10.1016/j.bioorg.2018.06.017
K. El-Adl, A.-G. A. El-Helby, H. Sakr, R. R. Ayyad, H. A. Mahdy, M. Nasser, H. S. Abulkhair, S. S. A. El-Hddad, Arch. Pharm. (Weinheim) 2020. https://doi.org/10.1002/ardp.202000279
Ö. E. Erkec, O. Arihan, Epilepsi 2015, 21, 6. https://doi.org/10.5505/epilepsi.2015.08108
T. Shimada, K. Yamagata, J. Vis. Exp. 2018, 136, e56573. https://doi.org/10.3791/56573
H. S. White, M. Johnson, H. H. Wolf, H. J. Kupferberg, Ital. J. Neurol. Sci. 1995, 16, 73. https://doi.org/10.1007/BF02229077
J. S. Tan, F. Lin, M. A. Tanouye, Brain Res. 2004, 1020, 45. https://doi.org/10.1016/j.brainres.2004.05.111
J. M. S. Pearce, J. Neurol., Neurosurg. Psychiatry 2002, 72, 412. https://doi.org/10.1136/jnnp.72.3.412
C. Narangoda, S. N. Sakipov, M. G. Kurnikova, ACS Chem. Neurosci. 2019, 10, 4511. https://doi.org/10.1021/acschemneuro.9b00344
I. Kufareva, R. Abagyan, Methods of Protein Structure Comparison, Springer, Basel, Switzerland 2011, pp. 231. https://doi.org/10.1007/978-1-61779-588-6_10
M. V. Yelshanskaya, A. K. Singh, J. M. Sampson, C. Narangoda, M. Kurnikova, A. I. Sobolevsky, Neuron 2016, 91, 1305. https://doi.org/10.1016/j.neuron.2016.08.012
C. A. Lipinski, F. Lombardo, B. W. Dominy, P. J. Feeney, Adv. Drug Deliv. Rev. 1997, 23, 3. https://doi.org/10.1016/S0169-409X(96)00423-1
D. E. V. Pires, T. L. Blundell, D. B. Ascher, pkCSM: J. Med. Chem. 2015, 58, 4066. https://doi.org/10.1021/acs.jmedchem.5b00104
A. Beig, R. Agbaria, A. Dahan, PLOS One 2013, 8, e68237. https://doi.org/10.1371/journal.pone.0068237
A. Hebert, M. Bishop, D. Bhattacharyya, K. Gleason, S. Torosian, Appl. Nanosci. 2015, 5, 763. https://doi.org/10.1007/s13204-014-0373-7
S. Roy, M. K. Mathew, J. Biol. Chem. 2018, 293, 4289. https://doi.org/10.1074/jbc.RA117.000432
X. Wu, Q. Zhang, J. Hu, SAR QSAR Environ. Res. 2016, 27, 147. https://doi.org/10.1080/1062936X.2015.1137353
K. El-Adl, M. K. Ibrahim, F. Khedr, H. S. Abulkhair, I. H. Eissa, Arch. Pharm. (Weinheim) 2020, e202000219. https://doi.org/10.1002/ardp.202000219
K. M. El-Gamal, M. S. Hagrs, H. S. Abulkhair, Bull. Fac. Pharm., Cairo University 2016, 54, 263. https://doi.org/10.1016/j.bfopcu.2016.08.002