Synthesis and anticonvulsant activities of novel 2-(cyclopentylmethylene)hydrazinyl-1,3-thiazoles in mouse models of seizures

References

• Blanco MM, dos Santos JG Jr, Perez-Mendes P, et al. Assessment of seizure susceptibility in pilocarpine epileptic and nonepileptic Wistar rats and of seizure reinduction with pentylenetetrazole and electroshock models. Epilepsia 2009;50:824–31
   PubMed Web of Science ®Google Scholar
• Löscher W. Critical review of current animal models of seizures and epilepsy used in the discovery and development of new antiepileptic drugs. Seizure 2011;20:359–68
   PubMed Web of Science ®Google Scholar
• Löscher W, Schmidt D. Modern antiepileptic drug development has failed to deliver: ways out of the current dilemma. Epilepsia 2011;52:657–78
   PubMed Web of Science ®Google Scholar
• Pasqualotto AC, Thiele KO, Goldani LZ. Novel triazole antifungal drugs: focus on isavuconazole, ravuconazole and albaconazole. Curr Opin Investig Drugs 2010;11:165–74
   PubMed Web of Science ®Google Scholar
• Das J, Chen P, Norris D, et al. 2-Aminothiazole as a novel kinase inhibitor template. Structure-activity relationship studies toward the discovery of N-(2-chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)-1- piperazinyl))-2-methyl-4-pyrimidinyl]amino))-1,3-thiazole-5-carboxamide (Dasatinib, BMS-354825) as a potent pan-Src kinase inhibitor. J Med Chem 2006;49:6819–32
   PubMed Web of Science ®Google Scholar
• Zeldin RK, Petruschke RA. Pharmacological and therapeutic properties of ritonavir-boosted protease inhibitor therapy in HIV-infected patients. J Antimicrob Chemother 2004;53:4–9
   PubMed Web of Science ®Google Scholar
• Fox LM, Saravolatz LD. Nitazoxanide: a new thiazolide antiparasitic agent. Clin Infect Dis 2005;40:1173–80
   PubMed Web of Science ®Google Scholar
• Rehman MZ, Anwar CJ, Ahmad S. An efficient synthesis of 2-alkyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxides. Bull Korean Chem Soc 2005;26:1771–5
   Web of Science ®Google Scholar
• Chimenti F, Secci D, Bolasco A, et al. Synthesis and selective inhibition of human monoamine oxidases of a large scaffold of (4,5-substituted-thiazol-2-yl)hydrazones. Med Chem Commun 2010;1:61–72
   Web of Science ®Google Scholar
• Chimenti F, Secci D, Bolasco A, et al. Synthesis, semipreparative HPLC separation, biological evaluation, and 3D-QSAR of hydrazothiazole derivatives as human monoamine oxidase B inhibitors. Bioorg Med Chem 2010;18:5063–70
   PubMed Web of Science ®Google Scholar
• Siddiqui N, Ahsan W. Triazole incorporated thiazoles as a new class of anticonvulsants: design, synthesis and in vivo screening. Eur J Med Chem 2010;45:1536–43
   PubMed Web of Science ®Google Scholar
• Ahangar N, Ayati A, Alipour E, et al. 1-((2-Arylthiazol-4-yl)methyl)azoles as a new class of anticonvulsants: design, synthesis, in vivo screening, and in silico drug-like properties. Chem Biol Drug Des 2011;78:844–52
   PubMed Web of Science ®Google Scholar
• Bineshmarvasti M, Sharifzadeh M, Jalilian AR, et al. Synthesis and anticonvulsant activity of N4-substituted triazoly thiazoles. DARU 2003;11:74–8
   Google Scholar
• Łączkowski KZ, Misiura K, Świtalska M, et al. Synthesis and in vitro antiproliferative activity of thiazole-based nitrogen mustards. The hydrogen bonding interaction between model systems and nucleobases. Anti-Cancer Agents Med Chem 2014;14:1271–81
   PubMed Web of Science ®Google Scholar
• Łączkowski KZ, Misiura K, Biernasiuk A, et al. Synthesis, in vitro biological screening and molecular docking studies of novel camphor-based thiazoles. Med Chem 2014;10:600–8
   PubMed Web of Science ®Google Scholar
• Łączkowski KZ, Motylewska K, Baranowska-Łączkowska A, et al. Synthesis, antimicrobial evaluation and theoretical prediction of NMR chemical shifts of thiazole and selenazole derivatives with high antifungal activity against Candida spp. J Mol Struct 2016;1108:427–37
   Web of Science ®Google Scholar
• Łączkowski KZ, Misiura K, Biernasiuk A, et al. Synthesis and antimicrobial activities of novel 6-(1,3-thiazol-4-yl)-1,3-benzoxazol-2(3H)-one derivatives. Heterocycl Commun 2014;20:41–6
   Web of Science ®Google Scholar
• Łączkowski KZ, Misiura K, Biernasiuk A, et al. Synthesis, antimicrobial activities and molecular docking studies of novel 6-hydroxybenzofuran-3(2H)-one based 2,4-disubstituted 1,3-thiazoles. Lett Drug Des Discov 2013;10:798–807
   Web of Science ®Google Scholar
• Łuszczki JJ, Czernecki R, Dudra-Jastrzębska M, et al. Influence of agmatine on the protective action of numerous antiepileptic drugs against pentetrazole-induced seizures in mice. Pharmacol Rep 2009;61:252–60
   PubMed Web of Science ®Google Scholar
• Sałat K, Podkowa A, Kowalczyk P, et al. Anticonvulsant active inhibitor of GABA transporter subtype 1, tiagabine, with activity in mouse models of anxiety, pain and depression. Pharmacol Rep 2015;67:465–72
   PubMed Web of Science ®Google Scholar
• Wilhelm EA, Jesse CR, Roman SS, et al. Anticonvulsant effect of (E)-2-benzylidene-4-phenyl-1,3-diselenole in a pilocarpine model in mice. Life Sci 2010;87:620–7
   PubMed Web of Science ®Google Scholar
• Sałat K, Kulig K, Gajda J, et al. Evaluation of anxiolytic-like, anticonvulsant, antidepressant-like and antinociceptive properties of new 2-substituted 4-hydroxybutanamides with affinity for GABA transporters in mice. Pharmacol Biochem Behav 2013;110:145–53
   PubMed Web of Science ®Google Scholar
• Litchfield JT, Wilcoxon E. A simplified method of evaluating dose-effect experiments. J Pharmacol Exp Ther 1949;96:99–13
   PubMed Web of Science ®Google Scholar
• Łączkowski KZ, Misiura K, Biernasiuk A, Malm A. Discovery and evaluation of efficient selenazoles with high antifungal activity against Candida spp. Med Chem 2015;11:118–27
   PubMed Web of Science ®Google Scholar
• Cirilli R, Ferretti R, La Torre F, et al. High-performance liquid chromatographic separation of enantiomers and diastereomers of 2-methylcyclohexanone thiosemicarbazone, and determination of absolute configuration and configurational stability. J Chromatogr A 2007;1172:160–9
   PubMed Web of Science ®Google Scholar
• Kamiński K, Zagaja M, Łuszczki JJ, et al. Design, synthesis, and anticonvulsant activity of new hybrid compounds derived from 2-(2,5-dioxopyrrolidin-1-yl)propanamides and 2-(2,5-dioxopyrrolidin-1-yl)butanamides. J Med Chem 2015;58:5274–86
   PubMed Web of Science ®Google Scholar