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Synthesis, biological evaluation, and docking studies of some 5-chloro-2(3H)-benzoxazolone Mannich bases derivatives as cholinesterase inhibitors.
Arch Pharm (Weinheim). 2018 Apr; 351(3-4):e1700273.AP

Abstract

A series of N-substituted-5-chloro-2(3H)-benzoxazolone derivatives were synthesized and evaluated for their acetylcholinesterase (AChE), butyrylcholinesterase (BuChE) inhibitory, and antioxidant activities. The structures of the title compounds were confirmed by spectral and elemental analyses. The cholinesterase (ChE) inhibitory activity studies were carried out using Ellman's colorimetric method. The free radical scavenging activity was also determined by in vitro ABTS (2,2-azinobis(3-ethylbenzothiazoline-6-sulfonic acid)) assay. The biological activity results revealed that all of the title compounds displayed higher AChE inhibitory activity than the reference compound, rivastigmine, and were selective for AChE. Among the tested compounds, compound 7 exhibited the highest inhibition against AChE (IC50 = 7.53 ± 0.17 μM), while compound 11 was found to be the most active compound against BuChE (IC50 = 17.50 ± 0.29 μM). The molecular docking study of compound 7 showed that this compound can interact with the catalytic active site (CAS) of AChE and also has potential metal chelating ability and a proper log P value. On the other hand, compound 2 bearing a methyl substituent at the ortho position on the phenyl ring showed better radical scavenging activity (IC50 = 1.04 ± 0.04 mM) than Trolox (IC50 = 1.50 ± 0.05 mM).

Authors+Show Affiliations

Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Ege University, Izmir, Turkey.Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Ege University, Izmir, Turkey.Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Ege University, Izmir, Turkey.Faculty of Pharmacy, Department of Biochemistry, Ege University, Izmir, Turkey.Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Ege University, Izmir, Turkey.Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Ege University, Izmir, Turkey.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

29527733

Citation

Uysal, Sirin, et al. "Synthesis, Biological Evaluation, and Docking Studies of some 5-chloro-2(3H)-benzoxazolone Mannich Bases Derivatives as Cholinesterase Inhibitors." Archiv Der Pharmazie, vol. 351, no. 3-4, 2018, pp. e1700273.
Uysal S, Parlar S, Tarikogullari AH, et al. Synthesis, biological evaluation, and docking studies of some 5-chloro-2(3H)-benzoxazolone Mannich bases derivatives as cholinesterase inhibitors. Arch Pharm (Weinheim). 2018;351(3-4):e1700273.
Uysal, S., Parlar, S., Tarikogullari, A. H., Aydin Kose, F., Alptuzun, V., & Soyer, Z. (2018). Synthesis, biological evaluation, and docking studies of some 5-chloro-2(3H)-benzoxazolone Mannich bases derivatives as cholinesterase inhibitors. Archiv Der Pharmazie, 351(3-4), e1700273. https://doi.org/10.1002/ardp.201700273
Uysal S, et al. Synthesis, Biological Evaluation, and Docking Studies of some 5-chloro-2(3H)-benzoxazolone Mannich Bases Derivatives as Cholinesterase Inhibitors. Arch Pharm (Weinheim). 2018;351(3-4):e1700273. PubMed PMID: 29527733.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis, biological evaluation, and docking studies of some 5-chloro-2(3H)-benzoxazolone Mannich bases derivatives as cholinesterase inhibitors. AU - Uysal,Sirin, AU - Parlar,Sulunay, AU - Tarikogullari,Ayse H, AU - Aydin Kose,Fadime, AU - Alptuzun,Vildan, AU - Soyer,Zeynep, Y1 - 2018/03/12/ PY - 2017/08/22/received PY - 2018/02/19/revised PY - 2018/02/20/accepted PY - 2018/3/13/pubmed PY - 2018/10/20/medline PY - 2018/3/13/entrez KW - 2(3H)-benzoxazolone KW - Mannich KW - antioxidant activity KW - cholinesterase inhibitors KW - molecular docking SP - e1700273 EP - e1700273 JF - Archiv der Pharmazie JO - Arch. Pharm. (Weinheim) VL - 351 IS - 3-4 N2 - A series of N-substituted-5-chloro-2(3H)-benzoxazolone derivatives were synthesized and evaluated for their acetylcholinesterase (AChE), butyrylcholinesterase (BuChE) inhibitory, and antioxidant activities. The structures of the title compounds were confirmed by spectral and elemental analyses. The cholinesterase (ChE) inhibitory activity studies were carried out using Ellman's colorimetric method. The free radical scavenging activity was also determined by in vitro ABTS (2,2-azinobis(3-ethylbenzothiazoline-6-sulfonic acid)) assay. The biological activity results revealed that all of the title compounds displayed higher AChE inhibitory activity than the reference compound, rivastigmine, and were selective for AChE. Among the tested compounds, compound 7 exhibited the highest inhibition against AChE (IC50 = 7.53 ± 0.17 μM), while compound 11 was found to be the most active compound against BuChE (IC50 = 17.50 ± 0.29 μM). The molecular docking study of compound 7 showed that this compound can interact with the catalytic active site (CAS) of AChE and also has potential metal chelating ability and a proper log P value. On the other hand, compound 2 bearing a methyl substituent at the ortho position on the phenyl ring showed better radical scavenging activity (IC50 = 1.04 ± 0.04 mM) than Trolox (IC50 = 1.50 ± 0.05 mM). SN - 1521-4184 UR - https://www.unboundmedicine.com/medline/citation/29527733/Synthesis_biological_evaluation_and_docking_studies_of_some_5_chloro_2_3H__benzoxazolone_Mannich_bases_derivatives_as_cholinesterase_inhibitors_ L2 - https://doi.org/10.1002/ardp.201700273 DB - PRIME DP - Unbound Medicine ER -