Cu-Catalyzed and iodine mediated synthesis of thioaurones <i>via in situ</i> C–S bond generation using xanthate as a sulfur surrogate

Soundarya, Palanisamy; Sekar, Govindasamy

doi:10.1039/d2ob01211a

Cited by 5 publications

(3 citation statements)

References 44 publications

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“…In Method IV, the orto-halogenated (I or Br) chalcone 47 is cyclized to a thioaurone core through the reaction with xanthate 48 , an odorless sulfur surrogate. In the presence of CuI and I 2 as catalysts, the chalcone is selectively iodinated in the α position, with the consequent univocal cyclization of the saturated ketone to the thioaurone nucleus; thanks to this peculiar mechanism of action, the cyclization to the six-membered thioflavone is avoided [ 66 ].…”

Section: Bioisosteric Scaffold-hopped Analogues Of Natural Auronesmentioning

confidence: 99%

Scaffold-Hopping Strategies in Aurone Optimization: A Comprehensive Review of Synthetic Procedures and Biological Activities of Nitrogen and Sulfur Analogues

La Monica,

Alamia,

Bono

et al. 2024

Molecules

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Aurones, particular polyphenolic compounds belonging to the class of minor flavonoids and overlooked for a long time, have gained significative attention in medicinal chemistry in recent years. Indeed, considering their unique and outstanding biological properties, they stand out as an intriguing reservoir of new potential lead compounds in the drug discovery context. Nevertheless, several physicochemical, pharmacokinetic, and pharmacodynamic (P3) issues hinder their progression in more advanced phases of the drug discovery pipeline, making lead optimization campaigns necessary. In this context, scaffold hopping has proven to be a valuable approach in the optimization of natural products. This review provides a comprehensive and updated picture of the scaffold-hopping approaches directed at the optimization of natural and synthetic aurones. In the literature analysis, a particular focus is given to nitrogen and sulfur analogues. For each class presented, general synthetic procedures are summarized, highlighting the key advantages and potential issues. Furthermore, the biological activities of the most representative scaffold-hopped compounds are presented, emphasizing the improvements achieved and the potential for further optimization compared to the aurone class.

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Section: Bioisosteric Scaffold-hopped Analogues Of Natural Auronesmentioning

confidence: 99%

Scaffold-Hopping Strategies in Aurone Optimization: A Comprehensive Review of Synthetic Procedures and Biological Activities of Nitrogen and Sulfur Analogues

La Monica,

Alamia,

Bono

et al. 2024

Molecules

View full text Add to dashboard Cite

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“…The authors have cited additional references within the Supporting Information. [25][26][27][28][29][30] The supporting information includes physical and spectral (NMR and mass) data and figures…”

Section: Supporting Information Summarymentioning

confidence: 99%

“…The authors have cited additional references within the Supporting Information [25–30] . The supporting information includes physical and spectral (NMR and mass) data and figures (S1–52), including spectra and MTT assay of lead compounds against hPBMCs.…”

Section: Supporting Information Summarymentioning

confidence: 99%

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

Kaur,

Suman,

Arora

et al. 2023

ChemistrySelect

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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.

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Hemiindigoids as Prominent Photoswitch Scaffolds

Gernet,

Toursel,

Balivet

et al. 2024

ChemPhotoChem

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Hemiindigo photoswitches, a class of chromophores derived from the well‐known indigo dye, have attracted considerable interest over the past two decades. These compounds are unique in their ability to absorb light in the visible region of the spectrum in both isomeric states, making them ideal for applications where high‐energy UV light is not tolerated. A particularly attractive feature of hemiindigoids is that, despite their rigid structures, they undergo significant and controllable changes during the photoisomerisation process. Moreover, they exhibit a combination of high thermal bistability, pronounced photochromism, and fast, efficient photoisomerisation, positioning hemiindigoid photoswitches as versatile chromophores. This review summarises the current developments and advances in hemiindigoid photoswitches, including their synthesis, photoswitching performance, and applications, with a strong focus on their practical use as reversible triggers in fields ranging from photopharmacology to advanced materials.

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Cu-Catalyzed and iodine mediated synthesis of thioaurones via in situ C–S bond generation using xanthate as a sulfur surrogate

Abstract: An efficient method for synthesizing thioaurones has been developed using xanthate as an odorless sulfur surrogate. This reaction's key success is using iodine as a reagent, which promotes the α-iodination...

Cited by 5 publications

References 44 publications

Scaffold-Hopping Strategies in Aurone Optimization: A Comprehensive Review of Synthetic Procedures and Biological Activities of Nitrogen and Sulfur Analogues

Scaffold-Hopping Strategies in Aurone Optimization: A Comprehensive Review of Synthetic Procedures and Biological Activities of Nitrogen and Sulfur Analogues

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

Hemiindigoids as Prominent Photoswitch Scaffolds

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