Synthesis and evaluation of the anticonvulsant activity of 8-alkoxy-4,5-dihydrobenzo[b][1,2,4]triazolo[4,3-d][1,4]thiazepine derivatives

References

• Strine TW, Kobau R, Chapman DP, et al. Psychological distress, comorbidities, and health behaviors among U.S. adults with seizures: results from the 2002 National Health Interview Survey. Epilepsia 2005;46:1133–9
   PubMed Web of Science ®Google Scholar
• Mc Namara OJ, Brunton LL, Lazo JS, Parker KL (Eds.). The pharmacological basis of therapeutics. New York: McGraw-Hill; 2006:501–26
   Google Scholar
• Sirven JI, Noe K, Hoerth M, Drazkowski J. Antiepileptic drugs 2012: recent advances and trends. Mayo Clin Proc 2012;87:879–89
   PubMed Web of Science ®Google Scholar
• Donner EJ, Snead OC. New generation anticonvulsants for the treatment of epilepsy in children. NeuroRX 2006;3:170–80
   Google Scholar
• Bootsma HP, Ricker L, Hekster YA, et al. The impact of side effects on long-term retention in three new antiepileptic drugs. Seizure 2009;18:327–31
   PubMed Web of Science ®Google Scholar
• Kennedy GM, Lhatoo SD. CNS adverse events associated with antiepileptic drugs. CNS Drugs 2008;22:739–60
   PubMed Web of Science ®Google Scholar
• Penovich PE, James Willmore L. Use of a new antiepileptic drug or an old one as first drug for treatment of absence epilepsy. Epilepsia 2009;50:37–41
   Google Scholar
• Bialer M, Johannessen SI, Kupferberg HJ, et al. Progress report on new antiepileptic drugs: a summary of the Eigth Eilat conference (EILAT VIII). Epilepsy Res 2007;73:1–52
   PubMed Web of Science ®Google Scholar
• Bialer M, Yagen B. Valproic acid -- second generation. Neurotherapeutics 2007;4:130–7
   PubMed Web of Science ®Google Scholar
• Alam O, Mullick P, Verma SP, et al. Synthesis, anticonvulsant and toxicity screening of newer pyrimidine semicarbazone derivatives. Eur J Med Chem 2010;45:2467–72
   PubMed Web of Science ®Google Scholar
• Karakurt A, Ozalp M, Isik S, et al. Synthesis, anticonvulsant and antimicrobial activities of some new 2-acetylnaphthalene derivatives. Bioorg Med Chem 2010;18:2902–11
   Google Scholar
• Tasso SM. Pharmacophore model for antiepileptic drugs acting on sodium channels. J Mol Model 2001;7:231–9
   Google Scholar
• Unverferth K, Engel J, Hofgen N, et al. Synthesis, anticonvulsant activity, and structureeactivity relationships of sodium channel blocking 3-aminopyrroles. J Med Chem 1998;41:63–73
   PubMed Web of Science ®Google Scholar
• Bruno-Blanch L, Galvez J, Garcia-Domenach R. Topological virtual screening: a way to find new anticonvulsant drugs from chemical diversity. Bioorg Med Chem Lett 2003;13:2749–54
   PubMed Web of Science ®Google Scholar
• Estrada E, Pena A. In silico studies for the rational discovery of anticonvulsant compounds. Bioorg Med Chem 2000;8:2755–70
   PubMed Web of Science ®Google Scholar
• Stefan H, Feuerstein TJ. Novel anticonvulsant drugs. Pharmacol Ther 2007;113:165–83
   PubMed Web of Science ®Google Scholar
• Eswaran S, Adhikari AV, Shetty NS. Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety. Eur J Med Chem 2009;44:4637–47
   PubMed Web of Science ®Google Scholar
• Bayrak H, Demirbas A, Demirbas N, Karaoglu SA. Synthesis of some new 1,2,4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activities. Eur J Med Chem 2009;44:4362–6
   PubMed Web of Science ®Google Scholar
• Patel NB, Khan IH, Rajani SD. Antimycobacterial and antimicrobial study of new 1,2,4-triazoles with benzothiazoles. Arch Pharm (Weinheim) 2010;343:692–9
   PubMed Web of Science ®Google Scholar
• Bahadur S, Singh SP, Shukla MK. Synthesis of some new thiosemicarbazides, thiadiazoles, triazoles and their derivatives as potential antiviral agents. Arch Pharm (Weinheim) 1982;315:312–7
   PubMed Web of Science ®Google Scholar
• Al-Soud YA, Al-Masoudi NA, Loddo R, Colla PL. In-vitro anti-HIV and antitumor activity of new 3,6-disubstituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles and thiadiazine analogues. Arch Pharm (Weinheim) 2008;341:365–9
   Google Scholar
• Al-Soud YA. Synthesis and anti-HIV activity of substituted 1,2,4-triazolo-thiophene derivatives. Heteroatom Chem 2007;18:443–8
   Web of Science ®Google Scholar
• Mathew V, Giles D, Keshavayya J, Vaidya VP. Studies on synthesis and pharmacological activities of 1,2,4-triazolo[3,4-b]1,3,4-thiadiazoles and their dihydro analogues. Arch Pharm (Weinheim) 2009;342:210–22
   PubMed Web of Science ®Google Scholar
• Deng XQ, Dong ZQ, Song MX, et al. Synthesis and anticonvulsant activities of some triazolothiadiazole derivatives. Arch Pharm (Weinheim) 2012;345:565–73
   PubMed Web of Science ®Google Scholar
• Xie ZF, Chai KY, Piao HR, et al. Synthesis and anticonvulsant activity of 7-alkoxyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinolines. Bioorg Med Chem Lett 2005;15:4803–5
   PubMed Web of Science ®Google Scholar
• Guo LJ, Wei CX, Jia JH, et al. Design and synthesis of 5-alkoxy-[1,2,4]triazolo[4,3-a]quinoline derivatives with anticonvulsant activity. Eur J Med Chem 2009;44:954–8
   PubMed Web of Science ®Google Scholar
• Zhang L, Guan LP, Sun XY, et al. Synthesis and anticonvulsant activity of 6-alkoxy-[1,2,4]triazolo[3,4-a]phthalazines. Chem Biol Drug Des 2009;73:313–19
   PubMed Web of Science ®Google Scholar
• Deng XQ, Wei CX, Li FN, et al. Design and synthesis of 10-alkoxy-5,6-dihydro-triazolo[4,3-d]benzo[f][1,4]oxazepine derivatives with anticonvulsant activity. Eur J Med Chem 2010;45:3080–6
   PubMed Web of Science ®Google Scholar
• Zhang LQ, Guan LP, Wei CX, et al. Synthesis and anticonvulsant activity of some 7-alkoxy-2H-1,4-benzothiazin-3(4H)-ones and 7-alkoxy-4H-[1,2,4]triazolo[4,3-d]benzo[b][1,4]thiazines. Chem Pharm Bull 2010;58:326–31
   PubMed Web of Science ®Google Scholar
• Deng XQ, Song MX, Wei CX, et al. Synthesis and anticonvulsant activity of 7-alkoxy-triazolo-[3,4-b]benzo[d]thiazoles. Med Chem 2010;6:313–20
   PubMed Web of Science ®Google Scholar
• Krall RJ, Penry JK, White BG, Kupferberg HJ. Antiepileptic drug development: II. Anticonvulsant drug screening. Epilepsia 1978;19:409–28
   PubMed Web of Science ®Google Scholar
• Poter RJ, Cereghino JJ, Gladding GD, et al. Antiepileptic drug development program. Cleve Clin Q 1984;51:293–305
   Google Scholar
• Arnoldi A, Bonsignori A, Melloni P, et al. Synthesis and anticonvulsant and sedative-hypnotic activity of 4-(alkylimino)-2,3-dihydro-4H-1-benzopyrans and -benzothiopyrans. J Med Chem 1990;33:2865–9
   PubMed Web of Science ®Google Scholar
• Löscher W, Schmidt D. Which animal models should be used in the search for new antiepileptic drugs? A proposal based on experimental and clinical considerations. Epilepsy Res 1988;2:145–81
   PubMed Web of Science ®Google Scholar
• Lipinski CA, Lombardo L, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 2001;46:3–26
   PubMed Web of Science ®Google Scholar
• Molinspiration Cheminformatics. Available from: http://www.molinspiration.com/ [last accessed 6 June 2012]
   Google Scholar
• Zhao Y, Abraham MH, Lee J, et al. Rate-limited steps of human oral absorption and QSAR studies. Pharm Res 2002;19:1446–57
   PubMed Web of Science ®Google Scholar
• Osiris property calculator. Available from: http://www.organic-chemistry.org/prog/peo [last accessed 8 June 2012]
   Google Scholar
• Rutkauskas K, Kantminiene K, Beresnevieius ZJ. Syn the sis and cyclization of N-{2-[(2-carboxyethyl)sulfanylphenyl]}-b-alanines. Polish J Chem 2008;82:2341–7
   Google Scholar
• White HS. Preclinical development of antiepileptic drugs: past, present, and future directions. Epilepsia 2003;44:2–8
   PubMedGoogle Scholar
• Levy RH, Mattson RH, Meldrum BS (Eds.). Antiepileptic drugs. New York: Raven Press; 1995:99–110
   Google Scholar
• Okada R, Negishi N, Nagaya H. The role of the nigrotegmental GABAergic pathway in the propagation of pentylenetetrazol-induced seizures. Brain Res 1989;480:383–7
   PubMed Web of Science ®Google Scholar
• Olsen RW. GABA-benzodiazepine-barbiturate receptor interactions. J. Neurochem 1981;37:1–13
   PubMed Web of Science ®Google Scholar
• Gale K. GABA and epilepsy: basic concepts from preclinical research. Epilepsia 1992;33:S3–12
   Google Scholar
• Loscher W. 3-Mercaptopropionic acid: convulsant properties, effects on enzymes of the gamma-aminobutyrate system in mouse brain and antagonism by certain anticonvulsant drugs, aminooxyacetic acid and gabaculine. Biochem Pharmacol 1979;28:1397–407
   PubMed Web of Science ®Google Scholar
• Macdonald RL, Barker JL. Specific antagonism of GABA-mediated postsynaptic inhibition in cultured mammalian spinal cord neurons: a common mode of convulsant action. Neurology 1978;28:325–30
   PubMed Web of Science ®Google Scholar
• Ertl P, Rohde B, Selzer P. Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties. J Med Chem 2000;43:3714–17
   PubMed Web of Science ®Google Scholar
• Palm K, Luthman K, Ungell AL, et al. Correlation of drug absorption with molecular surface properties. J Pharm Sci 1996;85:32–9
   PubMed Web of Science ®Google Scholar
• Schneeberger EE, Lynch RD. Structure, function and regulation of cellular tight junctions. Am J Physiol 1992;262:647–61
   PubMed Web of Science ®Google Scholar
• Kaliszan R, Markuszewski M. Brain/blood distribution described by a combination of partition coefficient and molecular mass. Int J Pharm 1996;145:9–16
   Web of Science ®Google Scholar
• Lien EJ, Liao RC, Shinouda HG. Quantitative structure-activity relationships and dipole moments of anticonvulsants and CNS depressants. J Pharm Sci 1979;68:463–5
   Google Scholar