The anticonvulsant activity of hydroxycoumarin derivatives and 4-[(3-nitro-2-oxo-2H-chromen-4-yl)amino] butanoic acid was studied using nicotine and corazole convulsion models. All investigated compounds protected animals from death in 100% of cases after intraperitoneal administration of the LD50 of nicotine (14 mg/kg). 4-[(3-Nitro-2-oxo-2H-chromen-4-yl)amino]butanoic acid showed anticonvulsant activity at a dose of 20 mg/kg in the corazole convulsion test while 7-(2-morpholino-2-oxoethoxy)-2H-chromen-2-one (a 7-hydroxycoumarin derivative) prevented convulsions at a dose of 200 mg/kg, which was comparable to the anticonvulsant effect of valproic acid at the same dose. An analysis of the results suggested different mechanisms for the anticonvulsant action of the investigated substances, which was indicative of good prospects for further development of coumarin derivatives as agents with wide spectra of anticonvulsant activity.
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References
E. V. Parfenova, F. K. Rider, A. G. Gersamiya, et al., Zh. Nevrol. Psikhiatr., 118(9), 77 – 85 (2018).
T. L. Mac, D. S. Tran, F. Quet, et al., Lancet Neurol., 6(6), 533 – 543 (2007).
T. R. Browne and G. L. Holmes, Handbook of Epilepsy, Lippincott Williams & Wilkins, Philadelphia (2004) [Russian translation, Binom, Moscow (2006)].
S. A. Gromov, N. A. Sivakova, E. A. Korsakova, et al., Obozr. Psikhiatr. Med. Psikhol., No. 3, 34 – 40 (2017).
S. A. Gromov and N. G. Naznanov (eds.), Epilepsy [in Russian], St. Petersburg (2015), pp. 839 – 857.
S. A. Gromov and N. G. Neznanov (eds.), Epilepsy [in Russian], St. Petersburg (2015), pp. 857 – 891.
P. D. Shabanov, Psychopharmacology [in Russian], N-L, St. Petersburg (2008).
D. J. Chong and A. M. Lerman, Curr. Neurol. Neurosci. Rep., 16(4), 39 – 42 (2016).
O. A. Pylaeva, K. Yu. Mukhin, and A. S. Petrukhin, Side Effects of Antiepileptic Therapy [in Russian], Vol. 236, Granat, Moscow (2016).
P. N. Patsalos, D. J. Berry, B. F. D. Bourgeois, et al., Epilepsia, 49(7), 1239 – 1276 (2008).
P. P. Denisenko and A. A. Tarasenko, RU Pat. 2,452,732, Jun. 10, 2012; Izobret. Polezn. Modeli, No. 16, 2012).
J. Bryda, M. Zagaja, A. Szewczyk, et al., Acta Neurobiol. Exp., 79, 126 – 132 (2019).
L. W. Hazleton, T. W. Tusing, B. R. Zeitlin, et al., J. Pharmacol. Exp. Ther., 118(3), 348 – 358 (1956).
M. L. Zinovieva and P. G. Zhminko, J. Pharm. Pharmacol., 5, 237 – 244 (2017).
M. O. Karatas, H. Uslu, S. Sari, et al., J. Enzyme Inhib., 31(5), 760 – 772 (2016).
M. Mohammadi-Khanaposhtani, N. Ahangar, S. Sobhani, et al., Bioorg. Chem., 89, 102989 – 102993 (2019).
A. P. Kourounakis, D. Xanthopoulos, and A. Tzara, Med. Res. Rev., 1 – 44 (2019).
P. D. Shabanov, L. V. Myznikov, et al., RU Pat. 2,655,929, May 30, 2018; Izobret. Polezn. Modeli, No. 16 (2018).
P. D. Shabanov, L. V. Myznikov, et al., RU Pat. 2,705,810, Nov. 12, 2019; Izobret. Polezn. Modeli, No. 32 (2019).
G. V. Mokrov, S. A. Litvinova, T. A. Voronina, et al., Med. Chem. Res., 28(11), 1901 – 1911 (2019).
V. P. Fisenko, Handbook of Experimental (Preclinical) Study of New Pharmacological Substances [in Russian], Remedium, Moscow (2000).
T. A. Voronina, L. N. Nerobokova, and A. N. Mironov (eds.), Handbook for Preclinical Drug Trials [in Russian], Part 1, Grif i K, Moscow (2012), pp. 235 – 250.
W. Loschere, D. Honack, C. P. Fassbendeer, et al., Epilepsy Res., 8(2), 171 – 189 (1991).
M. V. Veselovskaya, S. V. Shilin, and V. P. Khilya, Chem. Nat. Compd., 48(5), 757 – 760 (2012).
B. S. Diwakar, B. Govindh, Y. N. Sastry, et al., Med. Chem. Res., 24(4), 1546 – 1557 (2015).
R. U. Khabriev, Handbook of Experimental (Preclinical) Study of New Pharmacological Substances [in Russian], Meditsina, Moscow (2000).
A. N. Mironov, N. D. Bunyatyan, A. N. Vasil’ev, et al., Handbook for Preclinical Drug Trials [in Russian], Part 1, Grif i K, Moscow (2012).
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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 54, No. 9, pp. 22 – 26, September, 2020.
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Yakovleva, E.E., Myznikov, L.V. & Shabanov, P.D. Comparison of the Anticonvulsant Activities of Substituted Hydroxycoumarins and 4-[(3-Nitro-2-Oxo-2H-Chromen-4-Yl)Amino]Butanoic Acid. Pharm Chem J 54, 904–908 (2020). https://doi.org/10.1007/s11094-020-02294-9
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DOI: https://doi.org/10.1007/s11094-020-02294-9