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Synthesis and antioxidant activities of phenol derivatives from 1,6-bis(dimethoxyphenyl)hexane-1,6-dione.
- Source :
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Bioorganic chemistry [Bioorg Chem] 2020 Jul; Vol. 100, pp. 103884. Date of Electronic Publication: 2020 Apr 27. - Publication Year :
- 2020
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Abstract
- Starting from the compound (3,4-dimethoxyphenyl)(2-(3,4-dimethoxyphenyl)cyclopent-1-en-1-yl)methanone (4), two diols and three tetrol derivatives were synthesised. Morover, from the reactions of 1,3-dimethoxybenzene and 1,4-dimethoxybenzene with adipoyl chloride, fifteen new along with nine known compounds were obtained. For the characterizations of compounds, spectroscopic methods such as NMR including DEPT, COSY, HMQC and HMBC experiments and X-ray diffraction were used. The antioxidant activities of novel synthesized seventeen molecules were investigated by analytical methods like ABTS <superscript>•+</superscript> and DPPH <superscript>•</superscript> scavenging. Also, reducing power these molecules were investigated by Fe <superscript>3+</superscript> , Cu <superscript>2+</superscript> , and [Fe <superscript>3+</superscript> -(TPTZ) <subscript>2</subscript> ] <superscript>3+</superscript> . Some of the molecules record powerful antioxidant profile when compared to putative standards. The inhibition effects of the phenols compounds against AChE and BChE activities were analysed. Also, these phenols were found as effective inhibitors for AChE, hCA I, hCA II, and BChE with K <subscript>i</subscript> s in the range of 122.95 ± 18.41-351.31 ± 69.12 nM for hCA I, 62.35 ± 9.03-363.17 ± 180.1 nM for hCA II, 134.57 ± 3.99-457.43 ± 220.10 nM for AChE, and 27.06 ± 9.12-72.98 ± 9.53 nM for BChE, respectively.<br />Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.<br /> (Copyright © 2020 Elsevier Inc. All rights reserved.)
- Subjects :
- Antioxidants chemical synthesis
Antioxidants pharmacology
Carbonic Anhydrase I antagonists & inhibitors
Carbonic Anhydrase II antagonists & inhibitors
Carbonic Anhydrase Inhibitors chemical synthesis
Carbonic Anhydrase Inhibitors pharmacology
Chemistry Techniques, Synthetic
Cholinesterase Inhibitors chemical synthesis
Cholinesterase Inhibitors pharmacology
Crystallography, X-Ray
Hexanones chemical synthesis
Hexanones pharmacology
Humans
Models, Molecular
Phenols chemical synthesis
Phenols pharmacology
Antioxidants chemistry
Carbonic Anhydrase Inhibitors chemistry
Cholinesterase Inhibitors chemistry
Hexanones chemistry
Phenols chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1090-2120
- Volume :
- 100
- Database :
- MEDLINE
- Journal :
- Bioorganic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 32388430
- Full Text :
- https://doi.org/10.1016/j.bioorg.2020.103884