Synthesis and cholinesterase inhibitory activity of some phenylacetamide derivatives bearing 1H-pyrazole or 1H-1,2,4-triazole

Year 2016, Volume: 20 Issue: 1, 21 - 27, 26.10.2015

Ayşe Tarikoğulları , Murat Çizmecioğlu Merve Saylam Sülünay Parlar Vildan Alptüzün Zeynep Soyer

https://doi.org/10.12991/mpj.2016202105828

Abstract

A group of N-phenylacetamide derivatives bearing five membered heterocyclic rings, pyrazole or 1,2,4-triazole, were synthesized to investigate their cholinesterase inhibitory activities. Acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitory activities were evaluated by using Ellman’s spectroscopic method. Results indicated that all of the compounds displayed moderate and selective AChE inhibitory activity and the most active compound was 2-(1H-1,2,4-triazole-1-yl)-N-(3-methoxyphenyl)acetamide with an IC50 value of 6.68 mM. Docking studies were also carried out for the most active compound.

Keywords

Alzheimer’s disease, pyrazole, 1, 2, 4-triazole, acetamide, cholinesterase inhibitory activity

References

• References
• - Holzgrabe U, Kapkova P, Alptüzün V, Scheiber J, Kugelmann E. Targeting acetylcholinesterase to treat neurodegeneration. Expert Opin Ther Tar 2007; 11(2): 161-79.
• - Abramov AY, Canvari L, Duchen MRJ. Changes in intracellular calcium and glutathione in astrocytes as the primary mechanism of amyloid neurotoxicity. J Neurosci 2003; 15: 5088-95.
• - Barreio EJ, Camara CA, Verli H, Brazil-Mas L, Castro NG, Cintra WM, Arcava Y, Rodrigues CR, Fraga AM, Design, Synthesis, and Pharmacological Profile of Novel Fused Pyrazolo[4,3-d]pyridine and Pyrazolo[3,4-b][1,8]naphthyridine Isosteres: A New Class of Potent and Selective Acetylcholinesterase Inhibitors. J Med Chem 2003; 46: 1144-52.
• - Wang H, Zhang D, Wang F, Wu Y, Song H. Synthesis and Anticholinesterase Activity of (−)-Physostigmine Analogues with Modifications at C3a and C5. Chem Res Chin Univ 2013; 29(5): 888-93.
• - Sussman JL, Harel M, Frolow F, Oefner C, Goldman A, Toker L, Silman I. Atomic structure of acetylcholinesterase from Torpedo californica: a prototypic acetylcholine-binding protein. Science 1981; 253: 872-9.
• - Khan KM; Siddiqui S, Saleem M, Taha M, Saad SM, Perveen S, Choudhary MI. Synthesis of triazole Schiff bases: Novel inhibitors of nucleotide pyrophosphatase/phosphodiesterase-1, Bioorgan Med Chem 2014; 22: 6509–14.
• - Khan I, Ibrar A, Zaib S, Ahmad S, Furtmann N, Hameed S, Simpson J, Bajorath J, Iqbal J. Active compounds from a diverse library of triazolothiadiazole and triazolothiadiazine scaffolds: Synthesis, crystal structure, determination, cytotoxicity, cholinesterase inhibitory activity, and binding mode analysis. Bioorgan Med Chem 2014; 22: 6163-73.
• - Genest D, Rochais C, Lecoutey C, Santos JSO, Ballandonne C, Butt-Gueulle S, Legay R, Since M, Dallemagne P. Design, synthesis and biological evaluation of novel indano- and thiaindano-pyrazoles with potential interest for Alzheimer’s disease. Med Chem Commun 2013; 4: 925-31.
• - Razavi SF, Khoobi M, Nadri H, Sakhteman A, Moradi A, Emami S, Foroumadi A, Shafiee A. Synthesis and evaluation of 4-substituted coumarins as novel acetylcholinesterase inhibitors. Eur J Med Chem 2013; 64: 252-59.
• - Shi A, Huang L, Lu C, He F, Li X. Synthesis, biological evaluation and molecular modeling of novel triazole-containing berberine derivatives as acetylcholinesterase and b-amyloid aggregation inhibitors. Bioorgan Med Chem 2011; 19: 2298–2305.
• -Soyer Z, Parlar S, Alptuzun V. Synthesis and acetylcholinesterase (AChE) inhibitory activity of some N-substituted-5-chloro-2(3H)-benzoxazolone derivatives. Marmara Pharm J 2013; 17: 15-20.
• -Kumar H, Saini D, Jain S, Jain N. Pyrazole scaffold: A remarkable tool in the development of anticancer agents. Eur J Med Chem 2013; 70: 248-58.
• - Kumar A, Jain S, Parle M. Synthesis, biological evaluation and molecular modeling studies of 3-aryl-1- phenyl-1H-pyrazole derivatives as novel acetylcholinesterase inhibitors. Der Pharmacia Lettre, 2013; 5(4): 286-95.
• - Mohsen UA, Kocyigit-Kaymakcioglu B, Celen AO, Kaplancikli ZA. Some Urea and Thiourea Derivatives Bearing 1,2,4-Triazole Ring and Their Anti-Acetylcholinesterase Activities. MÜSBED 2014; 4(2): 85-9.
• - Yurttaş L , Kaplancıklı ZA, and Özkay Y. Design, synthesis and evaluation of new thiazole-piperazines as acetylcholinesterase inhibitors J Enzm Inhib Med Ch 2013; 28(5): 1040–1047.
• -Li M, Zhao BX. Progress of the synthesis of condensed pyrazole derivatives (from 2010 to mid-2013). Eur J Med Chem 2014; 85: 311-40.
• -Tarikoğulları AH, Kılıç FS, Erol K, Pabuçcuoğlu V. Synthesis and anticonvulsant activity of some alkanamide derivatives. Arzneimittel-Forsch 2010; 60(10): 593-8.
• - Alpan AS, Parlar S, Carlino L, Tarikogullari AH, Alptüzün V,Güneş HS. Synthesis, biological activity and molecular modeling studies on 1H-benzimidazole derivatives as acetylcholinesterase inhibitors. Bioorgan Med Chem 2013; 21(17): 4928-37.
• - Johnson JL, Cusack B, Davies MP, Fauq A, Rosenberry TL. Unmasking Tandem Site Interaction in Human Acetylcholinesterase. Substrate Activation with a Cationic Acetanilide Substrate. Biochemistry-us 2003; 42(18): 5438-52.
• - Gangi FED. Synthesis of some beta-dialkylaminopropioanilides. J Am Chem Soc 1955; XLIV: 135–7.
• - Zalaru C, Dumitrascu F, Draghici C, Cristea E, Tarcomnicu I. Pharmacologically active 2-(1H-pyrazol-1-yl)acetamides. Arkivoc 2009; 2: 308-14.
• -Ellman GL, Courtney KD, Andres V Jr, Feather-Stone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961; 7: 88-95.
• -Kapkova P, Stiefl N, Sürig U, Engels B, Baumann K, Holzgrabe U. Synthesis, biological activity, and docking studies of new acetylcholinesterase inhibitors of the bispyridinium type. Arch Pharm Chem 2003; 336(11): 523-40.
• -Molecular Operating Environment (MOE 2011.10) Chemical Computing Group Inc., 1010 Sherbrooke Street West, Suite 91, Monsteal H3A 2R7, Canada.
• -Jones G, Willett P, Glen RC, Leach AR, Taylor R. Development and validation of a genetic algorithm for flexible docking. J Mol Biol 1997; 267(3): 727-48.
• -Banerjee S, Ganguly S, Sen KK, Choowongkomon K, Seetaha S. Synthesis, evaluation and binding mode analysis of some novel
• triazole derivatives as antimicrobials. JAPER 2013; 3(4); 494-511.
• - Stankovsky S, Jedlovska E, Spirkova K. Synthesis of some triazolyl acetanilides. Collect Czech Chem C 1993; 58(9); 2211-14.
• - Hesse M, Meier H, Zeeh B. Spectroscopic Methods in Organic Chemistry. Stuttgart, New York. 1997.
• - Nakanishi K, Solomon PH. Infrared Absorption Spectroscopy. Emerson Adams Press Inc, San Francisco. 1977.
• - Galdeano C, Viayna E, Arroyo P, Bidon-Chanal, Blas JR, Munoz-Torrero D, Luque FJ. Structural Determinants of the Multifunctional Profile of Dual Binding Site Acetylcholinesterase Inhibitors as Anti-Alzheimer Agents. Curr Pharm Design 2010; 16: 2818-36.