3-Aryl-1-phenyl-1H-pyrazole derivatives as new multitarget directed ligands for the treatment of Alzheimer's disease, with acetylcholinesterase and monoamine oxidase inhibitory properties

EXCLI Journal

Volumn 12, Issue , 2013, Pages 1030-1042

  Kumar, Ashwani ^a   Jain, Sandeep ^a   Parle, Milind ^a   Jain, Neelam ^b   Kumar, Parvin ^c  

^a GURU JAMBHESHWAR UNIVERSITY OF SCIENCE AND TECHNOLOGY   (India)

^b BPS Mahila Vishwavidyalaya   (India)

^c KURUKSHETRA UNIVERSITY   (India)

Author keywords

1H pyrazole; AChE; Alzheimer's disease; MAO B; Molecular modeling

Indexed keywords

3 (4 CHOROPHENYL) 1 PHENYL 1H PYRAZOLE 4 CARBALDEHYDE; 3 (4 FLUOROPHENYL) 1 PHENYL 1H PYRAZOLE 4 CARBALDEHYDE; ACETYLCHOLINESTERASE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; CHOLINESTERASE INHIBITOR; DONEPEZIL; ESTERASE INHIBITOR; MONOAMINE OXIDASE INHIBITOR; N [[(4 FLUOROPHENYL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE]METHANAMINE; N [[3 (4 CHLOROPHENYL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE]BENZENAMINE; N [[3 (4 CHLOROPHENYL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE]ETHANAMINE; N [[3 (4 CHLOROPHENYL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE]ETHANOLAMINE; N [[3 (4 CHLOROPHENYL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE]METHANAMINE; N [[3 (4 CHLOROPHENYL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE]PROPAN 1 AMINE; N [[3 (4 FLUOROPHENYL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE]BENZENAMINE; N [[3 (4 FLUOROPHENYL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE]ETHANAMINE; N [[3 (4 FLUOROPHENYL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE]ETHANOLAMINE; N [[3 (4 FLUOROPHENYL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE]PROPAN 1 AMINE; OXIDOREDUCTASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG DESIGN; DRUG MECHANISM; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; IN VITRO STUDY; MALE; MOLECULAR MODEL; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

CAPRA HIRCUS; MUS;

EID: 84890329312     PISSN: None     EISSN: 16112156     Source Type: Journal    
DOI: None     Document Type: Article

References (32)

1. AutoDock Tools (version 1. 5. 6 rc2), Stefano Forte. Molecular Graphics Laboratory, Department of Molecular Biology, The Scripps Research Institute, 1999-2010; http://mgltools. scripps. edu.
2. Barnes LL, Wilson RS, Schneider JA, Bienias JL, Evans DA, Bennett DA. Gender, cognitive decline, and risk of AD in older persons. Neurology 2003; 60: 1777-81.
3. Bartolucci C, Siotto M, Ghidini E, Amari G, Bolzoni PT, Racchi M et al. Structural determinants of Torpedo californica acetylcholinesterase inhibition by the novel and orally active carbamate based anti-Alzheimer drug ganstigmine (CHF-2819). J Med Chem 2006; 49: 5051-8.
4. Bayazit V, Khan KM. Evaluation of Carbonic Anhydrase(CA) and Monoamine Oxidase (MAO) enzyme activations in organs and blood of goat (Capra aegagrus hircus). J Chem Soc Pak 2005; 27: 306-13.
5. BioToolKit320. Chang Bioscience Inc., 2005.
6. Bolea I, Juaŕez-Jimeńez J, Ri{dotless}ós C, Chioua M, Pouplana R, Luque FJ et al. Synthesis, biological evaluation, and molecular modeling of donepezil and N-[(5-(Benzyloxy)-1-methyl-1H-indol-2-yl)methyl]-N-methylprop-2-yn-1-amine hybrids as new multipotent cholinesterase/monoamine oxidase inhibitors for the treatment of Alzheimer's disease. J Med Chem 2011; 54: 8251-70.
7. Bolognesi ML, Rosini M, Andrisano V, Bartolini M, Minarini A, Tumiatti V et al. MTDL design strategy in the context of Alzheimer's disease: from lipocrine to memoquin and beyond. Curr Pharm Des 2009; 15: 601-13.
8. Cavalli A, Bolognesi ML, Minarini A, Rosini M, Tumiatti V, Recanatini M et al. Multi-target-directed ligands to combat neurodegenerative diseases. J Med Chem 2008; 51: 347-72.
9. Costa JS, Lopes JPB, Russowsky D, Petzhold CL, Borges ACA, Ceschi MA et al. Synthesis of tacrinelophine hybrids via one-pot four component reaction and biological evaluation as acetyl-and butyrylcholinesterase inhibitors. Eur J Med Chem 2013; 62: 556-63.
10. Cutler NR, Sramek JJ. Review of the next generation of Alzheimer's disease therapeutics: challenges for drug development. Prog Neuro-Psychopharmacol Biol Psychiatry 2001; 25: 27-57.
11. Discovery Studio v3. 5 client. Accelrys Software Inc., 2005-2012.
12. Dringenberg HC. Alzheimer's disease: more than a "cholinergic disorder": evidence that cholinergic-monominergic interactions contribute to EEG slowing and dementia. Behav Brain Res 2000; 115: 235-49.
13. Dunbrack RL. Rotamer libraries in 21st century. Curr Opin Struct Biol 2002; 12: 431-40.
14. Ellman GL, Courtney KD, Andres V, Featherstone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961; 7: 88-95.
15. Elsinghorst PW, Cieslik JS, Mohr K, Trankle C, Gutschow M. The first gallamine-tacrine hybrid: design and characterization at cholinesterases and the M2 muscarinic receptor. J Med Chem 2007; 50: 5685-95.
16. Garci{dotless}á-Alloza M, Gil-Bea FJ, Di{dotless}éz-Ariza M, Chen CP, Francis PT, Lasheras B et al. Cholinergic-serotonergic imbalance contributes to cognitive and behavioral symptoms in Alzheimer's disease. Neurophsychologia 2005; 43: 442-9.
17. Holt A, Sharman DF, Baker GB, Palcic MM. A continuous spectrophotometric assay for monoamine oxidase and related enzymes in tissue homogenates. Anal Biochem 1997; 244: 384-92.
18. Li RS, Wang XB, Hu XJ, Kong LY. Design, synthesis and evaluation of flavonoid derivatives as potential multifunctional acetylcholinesterase inhibitors against Alzheimer's disease. Bioorg Med Chem Lett 2013; 23: 2636-41.
19. MavinSketch 5. 10. 1 ChemAxon Ltd. 1998-2012. http://www. chemaxon. com.
20. Passos CS, Simões-Pires CA, Nurisso A, Soldi TC, Kato L, Oliveira CMA et al. Indole alkaloids of psychotria as multifunctional cholinesterases and monoamine oxidases inhibitors. Phytochemistry 2013; 86: 8-20.
21. Pettersen EF, Goddard TD, Huang CC, Couch GS, Greenblatt DM, Meng EC et al. UCSF chimera-a visualization system for exploratory research and analysis. J Comput Chem 2004; 25: 1605-12.
22. Strydom B, Bergh JJ, Petzer JP. Inhibition of monoamine oxidase by phthalide analogues. Bioorg Med Chem Lett 2013; 23: 1269-73.
23. Terry AV, Buccafusco JJ. The cholinergic hypothesis of age and Alzheimer's disease-related cognitive deficits: recent challenges and their implications for novel drug development. J Pharmacol Exp Ther 2003; 306: 821-7.
24. Terry AV, Buccafusco JJ, Wilson C. Cognitive dysfunction in neuropsychiatric disorders: selected serotonin receptor subtypes as therapeutic targets. Behav Brain Res 2008; 195: 30-8.
25. Trott O, Olson AJ. AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading. J Comput Chem 2010; 31: 455-61.
26. Trujillo-Ferrara J, Cano LM, Espinoza-Fonseca M. Synthesis, anticholinesterase activity and structure-activity relationships of m-aminobenzoic acid derivatives. Bioorg Med Chem Lett 2003; 13: 1825-7.
27. Ucar G, Gokhan N, Yesilada A, Bilgin A. 1-Nsubstituted thiocarbamoyl-3-phenyl-5-thienyl-2-pyrazolines: a novel cholinesterase and selective monoamine oxidase B inhibitors for the treatment of Parkinson's and Alzheimer's diseases. Neurosci Lett 2005; 382: 327-31.
28. Vogel HG (ed). Drug discovery and evaluation-pharmacological assays, 2nd ed. New York: Springer-Verlag, 2002 (pp 599-601).
29. Wang J, Wang W, Kollman PA, Case D. Automatic atom type and bond type perception in molecular mechanical calculations. J Mol Graph Model 2006; 25: 247.
30. Xie SS, Wang XB, Li JY, Yang L, Kong LY. Design, synthesis and evaluation of novel tacrinecoumarin hybrids as multifunctional cholinesterase inhibitors against Alzheimer's disease. Eur J Med Chem 2013; 64: 540-53.
31. Youdim MB, Buccafusco JJ. Multifunctional drugs for various CNS targets in the treatment of neurodegenerative disorders. Trends Pharmacol Sci 2005; 26: 27-35.
32. Youssef AM, White MS, Villanueva EB, El-Ashmawy IM, Klegeristo A. Synthesis and biological evaluation of novel pyrazolyl-2, 4-thiazolidinediones as anti-inflammatory and neuroprotective agents. Bioorg Med Chem 2010; 18: 2019-28.