760
Views
25
CrossRef citations to date
0
Altmetric
Research Article

Design, synthesis and anti-Parkinsonian evaluation of 3-alkyl/aryl-8-(furan-2-yl)thiazolo[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine-2(3H)-thiones against neuroleptic-induced catalepsy and oxidative stress in mice

, , &
Pages 818-826 | Received 19 Oct 2009, Accepted 12 Jan 2010, Published online: 30 Apr 2010

References

  • Jellinger KA. Formation and development of Lewy pathology: a critical update. J Neurol 2009;256:270–279.
  • Olanow CW. Oxidation reactions in Parkinson’s disease. Neurology 1990;40:32–39.
  • Markesbery WR, Jicha GA, Liu H, Schmitt FA. Lewy body pathology in normal elderly subjects. J Neuropathol Exp Neurol 2009;68:816–822.
  • Halliwell B. The wanderings of a free radical. Free Radic Biol Med 2009;46:531–542.
  • Beal MF. Mitochondria, oxidative damage, and inflammation in Parkinson’s disease. Ann N Y Acad Sci 2003;991:120–131.
  • Allain H, Bentue-Ferrer D, Akwa Y. Disease modifying drugs and Parkinson’s disease. Prog Neurobiol 2008;84:25–39.
  • Rascol O, Katzenschlager R. The treatment of early Parkinson’s disease. In: Hallett M, Poewe W ed. Therapeutics of Parkinson’s Disease and Other Movement Disorders. New York: John Wiley & Sons, 2008:49–70.
  • Stacy M, Galbreath A. Optimizing long-term therapy for Parkinson disease: levodopa, dopamine agonists, and treatment-associated dyskinesia. Clin Neuropharmacol 2008;31:51–56.
  • Azam F. Therapeutic Potential of Free Radical Scavengers in Neurological Disorders. In: Kozyrev D, Slutsky V, ed. Handbook of Free radicals: Formation, Types and Effects. New York: Nova Publishers, 2010; 57–97.
  • Gilgun-Sherki Y, Rosenbaum Z, Melamed E, Offen D. Antioxidant therapy in acute central nervous system injury: current state. Pharmacol Rev 2002;54:271–284.
  • Azam F, Alkskas IA, Khokra SL, Prakash O. Synthesis of some novel N4-(naphtha1,2-d]thiazol-2-yl)semicarbazides as potential anticonvulsants. Eur J Med Chem 2009;44:203–211.
  • Azam F. Synthesis of some urea and thiourea derivatives of naphtha[1,2-d]thiazol-2-amine as anti-Parkinsonian agents that cause neuroprotection against haloperidol-induced oxidative stress in mice. Med Chem Res 2009;18:287–308.
  • Azam F, Barodia SK, Anwer T, Alam MM. Neuroprotective effect of naphtha[1,2-d]thiazol-2-amine in an animal model of Parkinson’s disease. J Enzyme Inhib Med Chem 2009;24:808–817.
  • Azam F, Alkskas IA, Ahmed MA. Synthesis of some urea and thiourea derivatives of 3-phenyl/ethyl-2-thioxo-2,3-dihydrothiazolo[4,5-d]pyrimidine and their antagonistic effects on haloperidol-induced catalepsy and oxidative stress in mice. Eur J Med Chem 2009;44:3889–3897.
  • Nordvall, G; Ray, C; Rein, T; Sohn, D. Novel 5,7-disubstituted [1,3]thiazolo[4,5-d]Pyrimidin-2(3H)-one derivatives 794. US Patent 20090124637, May 14, 2009.
  • Nagahara K, Anderson JD, Kini GD, Dalley NK, Larson SB, Smee DF, Jin A, Sharma BS, Jolley WB. Thiazolo[4,5-d]pyrimidine nucleosides. The synthesis of certain 3-.beta.-D-ribofuranosylthiazolo[4,5-d]pyrimidines as potential immunotherapeutic agents. J Med Chem 1990;33:407–415.
  • Slee D, Lanier M, Vong BG, Chen Y, Zhang X, Lin E, Moorjani M, Castro P, Laria JC. Substituted pyrimidines as adenosine receptor antagonists. US Patent 20080275064, November 06, 2008.
  • Sugihara Y, Kawakita Y. Thiazolopyrimidine derivative. US Patent 20080269238, October 30, 2008.
  • Azam F, Ibn-Rajab IA, Alruiad AA. Adenosine A2A receptor antagonists as novel antiParkinsonian agents: A review of structure-activity relationships. Pharmazie 2009;64:771–795.
  • Wardas J, Konieczny J, Lorenc-Koci E. SCH 58261, an A2A adenosine receptor antagonist, counteracts parkinsonian-like muscle rigidity in rats. Synapse 2001;41:160–171.
  • Sanberg PR, Giordano M, Bunsey MD, Norman AB. The Catalepsy Test: Its Ups and Downs. Behav Neurosci 1988;102:748–759.
  • Ohkawa H, Ohishi N, Yagi K. Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction. Anal Biochem 1979;95:351–358.
  • Sedlak J, Lindsay RH. Estimation of total, protein-bound and non-protein sulfhydryl groups in tissue with Ellmann’s reagent. Anal Biochem 1968;25:192–205.
  • Sun Y, Oberley LW, Li Y. A simple method for clinical assay of superoxide dismutase Clin Chem 1988;34:497–500.
  • Paglia DE, Valentine WN. Studies on the quantitative and qualitative characterization of erythrocyte glutathione peroxidase. J Lab Clin Med 1967;70:158–170.
  • Lowry OH, Rosenbrough NJ, Farr AL, Randall RJ. Protein measurement with the folin phenol reagent. J Biol Chem 1951;193:265–275.
  • Zhao Y, Abraham MH, Le J, Hersey A, Luscombe CN, Beck G, Sherborne B, Cooper I. Rate-limited steps of human oral absorption and QSAR studies. Pharm Res 2002;19:1446–1457.
  • 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;43:37:14–3717.
  • 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 Delivery Rev 2001;46:3–26.
  • Molinspiration Cheminformatics, Bratislava, Slovak Republic, http://www.molinspiration.com/services/properties.html. Accessed on October 4, 2009.
  • Sanberg PR. Haloperidol-induced catalepsy is mediated by postsynaptic dopamine receptors. Nature 1980;284:472–473.
  • Ossowska K, Karcz M, Wardas J, Wolfarth S. Striatal and nucleus accumbens D1/D2 dopamine receptors in neuroleptic catalepsy. Eur J Pharmacol 1990;182:327–334.
  • Frank ST, Schmidt WJ. Burst activity of spiny projection neurons in the striatum encodes superimposed muscle tetani in cataleptic rats. Exp Brain Res 2003;152:519–522.
  • Correa M, Wisniecki A, Betz A, Dobson D.R, O’Neill M.F, O’Neill M.J, Salamone J.D. The adenosine A2A antagonist KF17837 reverses the locomotor suppression and tremulous jaw movements induced by haloperidol in rats: possible relevance to parkinsonism. Behav Brain Res 2004;148:47–54.
  • Calabrese V, Bates TE, Stella AM. NO synthase and NO-dependent signal pathways in brain aging and neurodegenerative disorders: the role of oxidant/antioxidant balance. Neurochem Res 2000;25:1315–1341.
  • Lohr JB, Kuczenski R, Niculescu AB. Oxidative mechanisms and tardive dyskinesia. CNS Drugs 2003;17:47–62.
  • Sagara Y. Induction of reactive oxygen species in neurons by haloperidol. J Neurochem 1998;71:1002–1012
  • Tsang AH, Chung KK. Oxidative and nitrosative stress in Parkinson’s disease. Biochim Biophys Acta 2009;1792:643–650.
  • Valko M, Leibfritz D, Moncol J, Cronin MTD, Mazur M, Telser J. Free radicals and antioxidants in normal physiological functions and human disease. Int J Biochem Cell Biol 2007;39:44–84.
  • Masella R, Di Benedetto R, Vari R, Filesi C, Giovannini C. Novel mechanisms of natural antioxidant compounds in biological systems: Involvement of glutathione and glutathione related enzymes. J Nutr Biochem 2005;16:577–586.
  • Martin HL, Teismann P. Glutathione—a review on its role and significance in Parkinson’s disease. FASEB J 2009;23:3263–3272.
  • Imam SZ, Ali SF. Selenium, an antioxidant, attenuates methamphetamine-induced dopaminergic toxicity and peroxynitrite generation. Brain Res 2000;855:186–191.
  • Pong K. Oxidative stress in neurodegenerative diseases: therapeutic implications for superoxide dismutase mimetics. Expert Opin Biol Ther 2003;3:127–139.
  • Avdeef A. Physicochemical profiling (solubility, permeability, and charge state). Curr Top Med Chem 2001;1:277–351.
  • Opera TI. Current trends in lead discovery: are we looking for the appropriate properties? J Comp Aided Mol Des. 2002;16:325–334.
  • Grande F, Aiello F, Grazia OD, Brizzi A, Garofalo A, Neamati N. Synthesis and antitumor activities of a series of novel quinoxalinhydrazides. Bioorg Med Chem 2007;15:288–294.
  • Yakaiah T, Lingaiah BP, Narsaiah B, Shireesha B, Ashok Kumar B, Gururaj S, Parthasarathy T, Sridhar B. Synthesis and structure-activity relationships of novel pyrimido1,2-b]indazoles as potential anticancer agents against A-549 cell lines. Bioorg Med Chem Lett 2007;17:3445–3453.
  • Kamal A, Khan MN, Srinivasa Reddy K, Rohini K. Synthesis of a new class of 2-anilino substituted nicotinyl arylsulfonylhydrazides as potential anticancer and antibacterial agents. Bioorg Med Chem 2007;15:1004–1013.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.