Synthesis, characterization Research Article www.jrespharm.com and investigation of cholinesterase enzyme inhibition and antioxidant activities of some 4-aryl-1,4-dihydropyridine derivatives

Hasan Erdinç Sellitepe; İnci Selin Doğan; Gamze Eroğlu; Burak Barut; Arzu Özel

Synthesis, characterization Research Article www.jrespharm.com and investigation of cholinesterase enzyme inhibition and antioxidant activities of some 4-aryl-1,4-dihydropyridine derivatives

Abstract

The aim of this study is to synthesize and characterize 4-aryl-1,4-dihydropyridine derivatives and evaluate their antioxidant and cholinesterase inhibitory properties. Hantzsch reaction was used in the synthesis of compounds; the compounds were prepared by the reaction of methyl 3- acetoacetate, appropriate aromatic aldehyde, ammonia and catalyst. The reactions were carried out in the presence of copper sulfate (for Method A) and boric acid /acetic acid catalyst (for Method B). CuSO4 was used as a catalyst for the Hantzsch reaction for the first time. The structure of the synthesized compounds were characterized by IR and 1H-NMR spectral studies. Furthermore, the enzym (acetylcholinesterase and butyrylcholinesterase) inhibition activity of the synthesized compounds was evaluated using Ellman's spectrophotometrical method as a novel approach. Antioxidant studies of the synthesized compounds were performed by measuring the 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay, phosphomolibdenum reducing antioxidant power assay, and metal chelating activity test. Results showed that 4-bromo substituted derivative (1b) has the highest antioxidant activity compared to other tested compounds. Moreover, compound 1b also has higher cholinesterase inhibitory effect (34.05 ± 2.23% and 24.93 ± 0.68% at 250 µM) than other tested compounds. In this study, eight 1,4-dihydropyridine derivatives, dimethyl 4-(phenyl/substituted phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5 dicarboxylate compounds were synthesized according to the Hantzsch reaction, using CuSO4 as a catalyst, for the first time. Compared to the classical reaction conditions, the presence of catalyst has been offered several advantages such as excellent good yields and short reaction times.

Keywords

References

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Details

Primary Language

English

Subjects

Pharmaceutical Biochemistry, Pharmaceutical Chemistry, Basic Pharmacology

Journal Section

Research Article

Authors

Hasan Erdinç Sellitepe
Türkiye

İnci Selin Doğan ^*
Türkiye

Gamze Eroğlu This is me
Türkiye

Burak Barut
Türkiye

Arzu Özel
Türkiye

Publication Date

June 27, 2025

Submission Date

June 14, 2019

Acceptance Date

June 24, 2019

Published in Issue

Year 2019 Volume: 23 Number: 4

IZ

https://izlik.org/JA54YM43MP

Cite

RIS / Bibtex

APA

Sellitepe, H. E., Doğan, İ. S., Eroğlu, G., Barut, B., & Özel, A. (2025). Synthesis, characterization Research Article www.jrespharm.com and investigation of cholinesterase enzyme inhibition and antioxidant activities of some 4-aryl-1,4-dihydropyridine derivatives. Journal of Research in Pharmacy, 23(4), 608-616. https://izlik.org/JA54YM43MP

AMA

1.Sellitepe HE, Doğan İS, Eroğlu G, Barut B, Özel A. Synthesis, characterization Research Article www.jrespharm.com and investigation of cholinesterase enzyme inhibition and antioxidant activities of some 4-aryl-1,4-dihydropyridine derivatives. J. Res. Pharm. 2025;23(4):608-616. https://izlik.org/JA54YM43MP

Chicago

Sellitepe, Hasan Erdinç, İnci Selin Doğan, Gamze Eroğlu, Burak Barut, and Arzu Özel. 2025. “Synthesis, Characterization Research Article Www.jrespharm.Com and Investigation of Cholinesterase Enzyme Inhibition and Antioxidant Activities of Some 4-Aryl-1,4-Dihydropyridine Derivatives”. Journal of Research in Pharmacy 23 (4): 608-16. https://izlik.org/JA54YM43MP.

EndNote

Sellitepe HE, Doğan İS, Eroğlu G, Barut B, Özel A (June 1, 2025) Synthesis, characterization Research Article www.jrespharm.com and investigation of cholinesterase enzyme inhibition and antioxidant activities of some 4-aryl-1,4-dihydropyridine derivatives. Journal of Research in Pharmacy 23 4 608–616.

IEEE

[1]H. E. Sellitepe, İ. S. Doğan, G. Eroğlu, B. Barut, and A. Özel, “Synthesis, characterization Research Article www.jrespharm.com and investigation of cholinesterase enzyme inhibition and antioxidant activities of some 4-aryl-1,4-dihydropyridine derivatives”, J. Res. Pharm., vol. 23, no. 4, pp. 608–616, June 2025, [Online]. Available: https://izlik.org/JA54YM43MP

ISNAD

Sellitepe, Hasan Erdinç - Doğan, İnci Selin - Eroğlu, Gamze - Barut, Burak - Özel, Arzu. “Synthesis, Characterization Research Article Www.jrespharm.Com and Investigation of Cholinesterase Enzyme Inhibition and Antioxidant Activities of Some 4-Aryl-1,4-Dihydropyridine Derivatives”. Journal of Research in Pharmacy 23/4 (June 1, 2025): 608-616. https://izlik.org/JA54YM43MP.

JAMA

1.Sellitepe HE, Doğan İS, Eroğlu G, Barut B, Özel A. Synthesis, characterization Research Article www.jrespharm.com and investigation of cholinesterase enzyme inhibition and antioxidant activities of some 4-aryl-1,4-dihydropyridine derivatives. J. Res. Pharm. 2025;23:608–616.

MLA

Sellitepe, Hasan Erdinç, et al. “Synthesis, Characterization Research Article Www.jrespharm.Com and Investigation of Cholinesterase Enzyme Inhibition and Antioxidant Activities of Some 4-Aryl-1,4-Dihydropyridine Derivatives”. Journal of Research in Pharmacy, vol. 23, no. 4, June 2025, pp. 608-16, https://izlik.org/JA54YM43MP.

Vancouver

1.Hasan Erdinç Sellitepe, İnci Selin Doğan, Gamze Eroğlu, Burak Barut, Arzu Özel. Synthesis, characterization Research Article www.jrespharm.com and investigation of cholinesterase enzyme inhibition and antioxidant activities of some 4-aryl-1,4-dihydropyridine derivatives. J. Res. Pharm. [Internet]. 2025 Jun. 1;23(4):608-16. Available from: https://izlik.org/JA54YM43MP