Triethylamin-mediated addition of 2-aminoethanethiol hydrochloride to chalcones: Synthesis of 3-(2-aminoethylthio)-1-(aryl)-3-(thiophen-2-yl) propan-1-ones and 5,7-diaryl-2,3,6, 7-tetrahydro-1,4-thiazepines

Gürdere, Meliha Burcu; Emeç, Ali Cemal; Aslan, Osman Nuri; Budak, Yakup; Ceylan, Mustafa

doi:10.1080/00397911.2016.1152585

Cited by 8 publications

(2 citation statements)

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“…This compound was synthesized according to a reported procedure . A solution of acetophenone (3.15 mL, 27 mmol) and benzaldehyde (2.7 mL, 27 mmol) in ethanol (120 mL) was added 1.1 mL of 6 M aqueous sodium hydroxide solution.…”

Section: Methodsmentioning

confidence: 99%

“…This compound was synthesized according to a reported procedure. 39 A solution of acetophenone (3.15 mL, 27 mmol) and benzaldehyde (2.7 mL, 27 mmol) in ethanol (120 mL) was added 1.1 mL of 6 M aqueous sodium hydroxide solution. The and the mixture was heated under reflux for 8 h. After completion of the reaction, as indicated by TLC, the mixture was dissolved in ethyl acetate (50 mL), washed with water, brine, dried (anhydrous Na 2 SO 4 ), and the solvent was evaporated under reduced pressure.…”

Section: ■ Experimental Proceduresmentioning

confidence: 99%

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Three-Component Synthesis of a Library of m-Terphenyl Derivatives with Embedded β-Aminoester Moieties

et al. 2018

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The three-component reaction between alkyl-or arylamines, β-ketoesters and chalcones in refluxing ethanol containing a catalytic amount of Ce(IV) ammonium nitrate allowed the construction of a large library of highly substituted dihydro-mterphenyl derivatives containing β-alkylaminoor β-arylamino ester moieties. This process generates three new bonds and one ring and proceeds in high atom economy, having two molecules of water as the only side product. Another domino process, in which the original MCR was telescoped with a subsequent aza Michael/retro-aza Michael sequence, allowed the one-pot preparation of a library of compounds with a N-unsubstituted β-aminoester fragment. Finally, to extend the structural diversity of these libraries, we also examined the aromatization of the central ring of our compounds in the presence of dichlorodicyanoquinone. This reaction sequence did not affect the integrity of a stereogenic center belonging to the amino component.

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Section: Methodsmentioning

confidence: 99%

Section: ■ Experimental Proceduresmentioning

confidence: 99%

Three-Component Synthesis of a Library of m-Terphenyl Derivatives with Embedded β-Aminoester Moieties

et al. 2018

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Synthesis, Antiproliferative and Cytotoxic Activities, DNA Binding Features and Molecular Docking Study of Novel Enamine Derivatives

Gürdere

Aydın

Yencilek

et al. 2020

Chemistry & Biodiversity

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Novel enamine derivatives were synthesized from the reaction of lactone and chalcones and their antiproliferative and cytotoxic activities against six cancer cell lines (e. g., HeLa, HT29, A549, MCF7, PC3 and Hep3B) and one normal cell lines (e. g., FL) were investigated along with their mode of interactions with CT‐DNA. Most of the enamine derivatives with IC50 values of 86–168 μM demonstrated much stronger antiproliferative activity than the starting molecules against the cancer cells. While, among the enamine derivatives, four compounds displayed higher cytotoxic potency than the control drugs (5‐fluorouracil and cisplatin) against the Hep3B cell lines, these compounds did not exhibit any significant toxicity against normal cells, FL. The UV/VIS spectral data suggest that eight compounds cause hypochromism with a slight bathochromic shift (∼6 nm), indicating that they bind to the DNA by way of an intercalative or minor groove binding mode. The binding constants of the compounds are in the range of 0.1×103 M−1–2.3×104 M−1. The antiproliferative activity of studied enamine derivatives could possibly be due to their DNA binding as well as their cytotoxic properties. In addition to these assays, the chalcones and enamine derivatives were investigated by molecular docking to calculate the synergistic effect of antiproliferative activities against six human cancer cell lines.

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ChemInform Abstract: Triethylamin‐Mediated Addition of 2‐Aminoethanethiol Hydrochloride to Chalcones: Synthesis of 3‐(2‐aminoethylthio)‐1‐(aryl)‐3‐(thiophen‐2‐yl)propan‐1‐ones and 5,7‐Diaryl‐2,3,6,7‐tetrahydro‐1,4‐thiazepines.

et al. 2016

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show abstract

Triethylamin-mediated addition of 2-aminoethanethiol hydrochloride to chalcones: Synthesis of 3-(2-aminoethylthio)-1-(aryl)-3-(thiophen-2-yl) propan-1-ones and 5,7-diaryl-2,3,6, 7-tetrahydro-1,4-thiazepines

Cited by 8 publications

References 20 publications

Three-Component Synthesis of a Library of m-Terphenyl Derivatives with Embedded β-Aminoester Moieties

Three-Component Synthesis of a Library of m-Terphenyl Derivatives with Embedded β-Aminoester Moieties

Synthesis, Antiproliferative and Cytotoxic Activities, DNA Binding Features and Molecular Docking Study of Novel Enamine Derivatives

ChemInform Abstract: Triethylamin‐Mediated Addition of 2‐Aminoethanethiol Hydrochloride to Chalcones: Synthesis of 3‐(2‐aminoethylthio)‐1‐(aryl)‐3‐(thiophen‐2‐yl)propan‐1‐ones and 5,7‐Diaryl‐2,3,6,7‐tetrahydro‐1,4‐thiazepines.

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