Thioaurones: Recent Advances in Synthesis, Reactivity, and Biological Activity

Bakhouch, Mohamed; Es-Sounni, Bouchra; Nakkabi, Asmae; Yazidi, Mohamed El

doi:10.2174/1570193x17999200719135019

Cited by 5 publications

(10 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Konieczny first reviewed the synthesis and reactivity of thioaurones 9 . Later, Yazidi described the recent synthesis of thioaurones and their reactions with various compounds 10 …”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthetic Approaches to (Z)‐Thioaurones

Lee

2021

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

(Z)‐Thioaurones were prepared by the condensation of 1‐benzothiophen‐3‐ones or 3‐acetoxybenzothiophene with arylaldehydes under basic or acidic conditions. Their derivatives were also prepared by reducing 2‐benzoybenzothiophen‐3‐ones and subsequent dehydration, cyclization of α,β‐unsaturated 1‐(2‐methylsulfinyl)phenyl ketone, and coupling of β‐chlorobenzothiophenone with arylboronic acids using Pd catalyst. Furthermore, (Z)‐thioaurones were prepared by the direct cyclization of α‐(phenylthio)cinnamic acids, 5‐exo cyclization of 2′‐(methylthio)chalcones, incorporation of a sulfur atom to 2′‐nitrochalcones and aromatic substitution, and deprotection of S‐protected alkynones and subsequent cyclization. Moreover, thioflavanone‐1‐oxides underwent ring contraction with I2 or NaOAc/Ac2O to give (Z)‐thioaurones.

show abstract

“…Konieczny first reviewed the synthesis and reactivity of thioaurones 9 . Later, Yazidi described the recent synthesis of thioaurones and their reactions with various compounds 10 …”

Section: Introductionmentioning

confidence: 99%

“…Currently, two reviews on the preparation of thioaurones and their reactions with various compounds have been published 9,10 . Neither reports did fully described the preparative methods of thioaurones.…”

Section: Introductionmentioning

confidence: 99%

Synthetic Approaches to (Z)‐Thioaurones

Lee

2021

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

show abstract

“…Aurones (4) are structural isomers of flavones and have a benzofuranone ring skeleton with 2-benzylidene groups. Thioaurones (5) and azaaurones (6) are the sulfur and aza analogs of aurones, respectively. Aurones contribute to the pigmentations of flowers and fruits, but thioaurones are not found in nature (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

“…4 Thioaurones are cytotoxic to cancer cells and have been utilized as the core of thioindigo dyes. 5 Azaaurones have leishmanicidal, antibacterial, and antimalarial activities. 6 The syntheses of flavones, 7 thioflavones, 2,8 and 2-phenyl-4-quinolones 3,9 have been reviewed by various synthetic strategies including condensation, oxidative cyclization, 1,4-addition, coupling, and the Wittig reaction.…”

Section: Introductionmentioning

confidence: 99%

“…6 The syntheses of flavones, 7 thioflavones, 2,8 and 2-phenyl-4-quinolones 3,9 have been reviewed by various synthetic strategies including condensation, oxidative cyclization, 1,4-addition, coupling, and the Wittig reaction. The syntheses of aurones, 10 thioaurones, 5,11 and azaaurones 6a have been also reviewed by synthetic methods including condensation, oxidative cyclization, and intramolecular cyclization.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

A review of the syntheses of (thio)flavones, 4‐quinolones, (thio)aurones, and azaaurones from 2′‐substituted alkynones

Lee

2021

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

Flavones have been prepared by the 6-endo cyclization of o-alkynoylphenols, cyclization/deprotection of 2 0 -protected alkynones, or carbonylative coupling of 2-halophenols with arylacetylenes and subsequent cyclization. (Z)-Aurones have been prepared by the 5-exo cyclization of o-alkynoylphenols or oxidation of (Z)-benzylidenebenzofuran-3-ols with MnO 2 . Thioflavones have been prepared by deprotection/6-endo cyclization of S-protected alkynones or by the addition of sulfur to 2 0 -halo(methoxy)alkynones and subsequent cyclization. Deprotection and 5-exo cyclization of S-benzylated alkynones using HCOOH afforded (Z)-thioaurones. 2-Phenyl-4-quinolones have been prepared by the 6-endo cyclization of 2 0 -aminoalkynones or by the addition of amines to 2 0haloalkynones and subsequent cyclization. Furthermore, the treatment of 2 0aminoalkynones with triphenylphosphine afforded (Z)-azaaurones by 5-exo cyclization.

show abstract

Design, Synthesis, and Anticancer Evaluation of Hemithioindigos via Inhibition of Human Topoisomerases

Kaur,

Suman,

Arora

et al. 2023

ChemistrySelect

View full text Add to dashboard Cite

Hemithioindigos were designed as topoisomerase inhibitors, synthesized, and evaluated for their anticancer properties against lung (A549) and breast (MDA‐MB‐468 and MCF7) cancer cell lines. Among all the synthetics, three compounds exerted potential anticancer effects on A549 (lung) and MCF7 (breast) cancer cell lines at low micromolar concentrations. The results revealed that two of these compounds blocked the cancer cells at the G1/S phase, while the third compound showed moderate G2/M inhibition, leading to necrotic cell death. Finally, the topoisomerase inhibition assays revealed their potent Topo I/II inhibitory actions as one of the primary anticancer mechanisms. Molecular docking studies further corroborated these findings.

show abstract

Thioaurones: Recent Advances in Synthesis, Reactivity, and Biological Activity

Cited by 5 publications

References 0 publications

Synthetic Approaches to (Z)‐Thioaurones

Synthetic Approaches to (Z)‐Thioaurones

A review of the syntheses of (thio)flavones, 4‐quinolones, (thio)aurones, and azaaurones from 2′‐substituted alkynones

Design, Synthesis, and Anticancer Evaluation of Hemithioindigos via Inhibition of Human Topoisomerases

Contact Info

Product

Resources

About