Novel benzo[b]xanthene derivatives: Bismuth(III) triflate-catalyzed one-pot synthesis, characterization, and acetylcholinesterase, glutathione S-transferase, and butyrylcholinesterase inhibitory properties.

Title Novel benzo[b]xanthene derivatives: Bismuth(III) triflate-catalyzed one-pot synthesis, characterization, and acetylcholinesterase, glutathione S-transferase, and butyrylcholinesterase inhibitory properties.
Authors K. Turhan; B. Pekta?; F. Türkan; F.T. Tu?cu; Z. Turgut; P. Taslimi; H.S. Karaman; I. Gulcin
Journal Arch Pharm (Weinheim)
DOI 10.1002/ardp.202000030
Abstract

In this study, 3,4-dihydro-12-aryl-1H-benzo[b]xanthene-1,6,11-(2H,12H)trione compounds were obtained through one-pot condensation of various substituted aromatic aldehydes, 2-hydroxy-1,4-naphthoquinone, and dimedone in the presence of Bi(OTf) as a green and reusable catalyst. The structural characterization of these novel substituted benzo[b]xanthenes was performed by spectroscopic methods, and their inhibitory actions against butyrylcholinesterase (BChE), acetylcholinesterase (AChE), and glutathione S-transferase (GST) were investigated. GST is an enzyme responsible for removing toxic molecules during Phase II reactions in the detoxification mechanism. The AChE and BChE enzymes, which are called cholinesterases, are among the enzymes that occur especially during dementia such as brain damage or Alzheimer's disease. Inhibition effects of the benzo[b]xanthene derivatives on AChE, BChE, and GST were found at the millimolar level. The best inhibitor for GST is compound 4a (31.18?±?6.13?mM), for AChE, it is compound 4d (28.16?±?3.46?mM), and for BChE, it is compound 4f (36.24?±?3.19?mM). Compound 4a inhibited the dimerization of GST subunits, and compounds 4d and 4f directly inhibited the catalytic activity by interacting with the catalytic active site or a related site of the AChE and BChE enzymes, respectively.

Citation K. Turhan; B. Pekta?; F. Türkan; F.T. Tu?cu; Z. Turgut; P. Taslimi; H.S. Karaman; I. Gulcin.Novel benzo[b]xanthene derivatives: Bismuth(III) triflate-catalyzed one-pot synthesis, characterization, and acetylcholinesterase, glutathione S-transferase, and butyrylcholinesterase inhibitory properties.. Arch Pharm (Weinheim). 2020:e2000030. doi:10.1002/ardp.202000030

Related Elements

Bismuth

See more Bismuth products. Bismuth (atomic symbol: Bi, atomic number: 83) is a Block P, Group 15, Period 6 element with an atomic radius of 208.98040. The number of electrons in each of Bismuth's shells is 2, 8, 18, 32, 18, 5 and its electron configuration is [Xe] 4f14 5d10 6s2 6p3. Bismuth Bohr ModelThe bismuth atom has a radius of 156 pm and a Van der Waals radius of 207 pm. In its elemental form, bismuth is a silvery white brittle metal. Bismuth is the most diamagnetic of all metals and, with the exception of mercury, its thermal conductivity is lower than any other metal. Elemental BismuthBismuth has a high electrical resistance, and has the highest Hall Effect of any metal (i.e., greatest increase in electrical resistance when placed in a magnetic field). Bismuth is found in bismuthinite and bismite. It is also produced as a byproduct of lead, copper, tin, molybdenum and tungsten extraction. Bismuth was first discovered by Early Man. The name Bismuth originates from the German word 'wissmuth,' meaning white mass.

Fluorine

Fluorine is a Block P, Group 17, Period 2 element. Its electron configuration is [He]2s22p5. The fluorine atom has a covalent radius of 64 pm and its Van der Waals radius is 135 pm. In its elemental form, CAS 7782-41-4, fluorine gas has a pale yellow appearance. Fluorine was discovered by André-Marie Ampère in 1810. It was first isolated by Henri Moissan in 1886.

Nitrogen

See more Nitrogen products. Nitrogen is a Block P, Group 15, Period 2 element. Its electron configuration is [He]2s22p3. Nitrogen is an odorless, tasteless, colorless and mostly inert gas. It is the seventh most abundant element in the universe and it constitutes 78.09% (by volume) of Earth's atmosphere. Nitrogen was discovered by Daniel Rutherford in 1772.

Sulfur

See more Sulfur products. Sulfur (or Sulphur) (atomic symbol: S, atomic number: 16) is a Block P, Group 16, Period 3 element with an atomic radius of 32.066. Sulfur Bohr ModelThe number of electrons in each of Sulfur's shells is 2, 8, 6 and its electron configuration is [Ne] 3s2 3p4. In its elemental form, sulfur has a light yellow appearance. The sulfur atom has a covalent radius of 105 pm and a Van der Waals radius of 180 pm. In nature, sulfur can be found in hot springs, meteorites, volcanoes, and as galena, gypsum, and epsom salts. Sulfur has been known since ancient times but was not accepted as an element until 1777, when Antoine Lavoisier helped to convince the scientific community that it was an element and not a compound.

Related Forms & Applications