Synthesis of novel 6-substituted-3(2H)-pyridazinone-2-acetyl-2- (substituted/-nonsubstituted benzal)hydrazone derivatives and acetylcholinesterase and butyrylcholinesterase inhibitory activities in vitro

Arzneimittel-Forschung/Drug Research

Volumn 61, Issue 1, 2011, Pages 1-7

  Utku, Semra ^a   Gökçe, Mehtap ^b   Orhan, Ilkay ^b   Şahin, M Fethi ^b  

^a MERSIN UNIVERSITY   (Turkey)

^b GAZI UNIVERSITY   (Turkey)

Author keywords

3(2 H ) pyridazinone; Acetylcholinesterase inhibitors; Benzal hydrazone; Butyrylcholinesterase inhibitors

Indexed keywords

ACETYLCHOLINESTERASE; CHOLINESTERASE; HYDRAZONE DERIVATIVE; PYRIDAZINONE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO STUDY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 79951866264     PISSN: 00044172     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0031-1296161     Document Type: Article

References (23)

1. Frank RA, Galasko D, Hampel H, Hardy J, de Leon MJ, Mehta PD, et al. Biological markers for therapeutic trials in Alzheimer's disease: Proceedings of the biological markers working group; NIA initiative on neuroimaging in Alzheimer's disease. Neurobiol Aging. 2003;24:521-36.
2. Mosconi L, Brys M, Glodzik-Sobanska L, De Santi S, Rusinek H, de Leon MJ. Early detection of Alzheimer's disease using neuroimaging. Exp Gerontol. 2007;42:129-38. (Pubitemid 44937821)
3. Beard CM, Kokmen E, Sigler C, Smith GE, Petterson T, O'Brien PC. Cause of death in Alzheimer's disease. Ann Epidemiol. 1996;6:195-200. (Pubitemid 26163145)
4. Sadashiva CT, Chandra JN, Ponnappa KC, Veerabasappa T. Synthesis and efficacy of 1-bis(4-fluorophenyl)-methyl]piperazine derivatives for acetylcholineesterase inhibition, as a stimulant of central cholinergic neurotransmission in Alzheimer's disease. BioorgMed Chem Lett. 2006;16:3932-6. (Pubitemid 44425197)
5. Pakaski M, Kalman J. Interactions between the amyloid and cholinergic mechanisms in Alzheimer's disease. Neurochem Int. 2008; 53:103-11.
6. Auld DS, Kornecook TJ, Bastianetto S, Quirion R. Alzheimer's disease and the basal forebrain cholinergic system: relations to β-amyloid peptides, cognition, and treatment strategies. Prog Neurobiol. 2002;68:209-45. (Pubitemid 35346805)
7. Ingram DK, Spangler EL, Iijima S, Ikari H, Kuo H, Greig NH, et al. Rodent models of memory dysfunction in Alzheimer's disease and normal aging: Moving beyond the cholinergic hypothesis. Life Sci. 1994;55:2037-49.
8. Masterman D. Cholinesterase inhibitors in the treatment of Alzheimer's disease and related dementias. Clin Geriat Med. 2004;20:59-68. (Pubitemid 38221463)
9. Zhang N, Casida JE. Novel irreversible butyrylcholinesterase inhibitors: 2-chloro-1-(substituted phenyl)ethylphosphonic Acids. Bioorg Med Chem. 2002;10(5):1281-90. (Pubitemid 34214692)
10. Reale M, Iarlori C, Gambi F, Feliciani C, Isabella L, Gambi D. The acetylcholinesterase inhibitor, Donepezil, regulates a Th2 bias in Alzheimer's disease patients. Neuropharmacol. 2006;50:606-13.
11. Shen Q, Peng Q, Shao J, Liu X, Huang Z, Pu X, et al. Synthesis and biological evaluation of functionalized coumarins as acetylcholinesterase inhibitors. Eur J Med Chem. 2005;40:1307-15. (Pubitemid 41618271)
12. X. Zhou, X. Wang, T. Wangb, L. Kong. Design, synthesis, and acetylcholinesterase inhibitory activity of novel coumarin analogues. Bioorg Med Chem. 2008;16:8011-21.
13. Boissier JR, Ratouis R, Dumont C. Synthesis and Pharmacological Study of New Piperazine Derivatives. Benzylpiperazines. J Med Chem. 1963;6(5):541-4.
14. Elvio B, Parravicini F, Emilio T. Hydrazino pyridazines containing basic groups in the 6-position and possessing hypotensive activity. Farmaco Ed Sci . 1969;24(11):919-29.
15. Gökçe M, Doǧruer D, Şahin MF. Synthesis and antinociceptive activity of 6-substituted-3(2H)-pyridazinone derivatives. Farmaco. 2001;56:221-4.
16. Gökçe M, Şahin MF, Küpeli E, Yeşilada E. Synthesis and analgesic and anti-inflammatory activity of new 3(2h)-pyridazinone derivatives. Arzneimittelforschung. 2004;54:396-401. (Pubitemid 38981740)
17. Şahin MF, Badiçoǧlu B, Gökçe M, Küpeli E, Yeşilada E. Synthesis and analgesic and antiinflammatory activity of methyl [6-substitue-3(2H)-piridazinone-2-yl]acetate derivatives. Arch PharmMed Chem. 2004;337:445-52. (Pubitemid 39243535)
18. Gökçe M, Bakir G, Şahin MF, Küpeli E, Yeşilada E. synthesis of new Mannich bases of arylpyridazinones as analgesic and anti-inflammatory agents. Arzneimittelforschung. 2005;55:318-25. (Pubitemid 40896698)
19. Dündar Y, Gökçe M, Küpeli E, Şahin, MF. Synthesis and analgesic and antiinflammatory activity of ethyl 6-substituted-3(2 H )-pyridazinone-2-ylacetate derivatives. Arzneimittelforschung. 2007;57:777-81.
20. Özçelik AB, Gökçe M, Orhan I, Kaynak F, Şahin MF. Synthesis and antimicrobial, acetylcholinesterase and butyrylcholinesterase inhibitory activities of novel ester and hydrazide derivatives of 3(2H)-pyridazinone. Arzneimittelforschung. 2010;60;452-8.
21. Ellman GL, Courtney KD, Andres V, Featherstone RM. A new and rapid colorimetricdetermination of acetylcholinesterase activity. Biochem Pharm. 1961;7:88-95.
22. Orhan I, Aslan S, Kartal M, Şener B, Başer KHC. Inhibitory effect of Turkish Rosmarinus officinalis L. on acetylcholinesterase and butyrylcholinesterase enzymes. Food Chem. 2008;108:663-8.
23. Gökçe M, Utku S, Küpeli E. Synthesis and analgesic and anti-inflammatory activities 6-substituted-3(2H)-pyridazinone-2-acetyl-2-(p- substituted/nonsubstituted benzal)hydrazone derivatives. Eur J Med Chem. 2009;44:3760-4.