Article 2022 · 5 citations

Synthesis and biological effects evaluation of benzoconduritols C and D from oxabenzonorbornadiene

Kelebekli, Latif, Yilmaz, Fatma Zehra, Col Ayvaz, Melek, Sahin, Ertan

Abstract

The effective synthesis of benzoconduritols C and D is reported. Oxidation of oxabenzonorbornadiene followed by acetylation with Ac2O/pyridine or AcCl/CH2Cl2 gave the corresponding exo-diacetate compound stereoselectively. Acid-catalyzed ring opening of the bridged ether bond (the 1,4-anhydo bond) with Ac2O in the oxabenzonorbornadiene system to produce benzoconduritol tetraacetates followed by ammonolysis furnished the desired benzoconduritols C and D, respectively. The novel benzoconduritols (9, 10, 15, 16, and 17) were evaluated for the first time in terms of their potential antioxidant, anti-inflammatory, and enzyme inhibition activities. Most of the complexes exhibited moderate activity. Especially 15 (IC50 = 0.374 mM) and 10 (IC50 = 0.450 mM) have better anti-inflammatory effect when compared to ibuprofen (IC50 = 0.437 mM). Furthermore, the benzoconduritol C 9 has better alpha-glucosidase inhibition potential with the IC50 value of 0.437 mM than acarbose (IC50 = 0.445 mM). The results of this study point out that most of these molecules have the potential to provide an alternative for the clinical control of inflammation and diabetes due to their anti-inflammatory and anti-glucosidase activities. Graphic abstract

Keywords

Acetylcholinesterase alpha-Glucosidase Anti-inflamatuar Benzoconduritols Ring opening of bridged ether STEREOSPECIFIC SYNTHESIS MUSHROOM TYROSINASE CONDURITOL DERIVATIVES STRATEGY GLYCOSYLATION GLUCOSIDASE INHIBITORS GLYCOSIDES HYDROLYSIS

WoS Categories

Chemistry, Multidisciplinary

Sustainable Development Goals

Good Health and Well-being

Citation

Journal: JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
Year: 2022
Volume: 19
Issue: 5
Pages: 1899-1912
ISSN: 1735-207X
eISSN: 1735-2428
DOI: 10.1007/s13738-021-02428-0
WoS UID: WOS:000709665000001

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