Phosphorous Acid Promoted Hydration–Condensation of Aromatic Alkynes with Aldehydes Affording Chalcones in an Oil/Water Two-Phase System

Zhou, Yongbo; Li, Zhongwen; Yang, Xiao; Xiu-lin, Chen; Li, Mei; Chen, Tieqiao; Yin, Shuang‐Feng

doi:10.1055/s-0035-1560832

Cited by 14 publications

(5 citation statements)

References 2 publications

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“…This metal-free method produces innocuous, water-soluble byproducts, such as iodide and sulfate salts, and uses inexpensive molecular iodine to facilitate the hydration. Moreover, unlike other metal-free alkyne hydration procedures, heat and strong acids are not required [17–20]. The reaction proceeds under mild conditions at room temperature.…”

Section: Resultsmentioning

confidence: 99%

Iodine-mediated hydration of alkynes on keto-functionalized scaffolds: mechanistic insight and the regiospecific hydration of internal alkynes

Lee

Jones

Nkengbeza

et al. 2019

Beilstein J. Org. Chem.

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An iodine-mediated hydration reaction of alkynes serves as a green alternative to metal-catalyzed procedures. Previous work has shown that this method works well with terminal alkynes on keto-functionalized scaffolds, including 1,3-dicarbonyls and their heteroatom analogues. It was hypothesized that the reaction proceeds through a 5-exo-dig neighboring group participation (NGP) cyclization and an α-iodo intermediate. The work described herein probes the existence of the intermediate through NMR investigations and explores the scope of the hydration process with internal alkynes. The NMR experiments confirm the existence of the α-iodo intermediate, and methodology studies demonstrate that alkyl-capped, asymmetric, internal alkynes undergo a regiospecific hydration, also via the 5-exo-dig NGP pathway.

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Section: Resultsmentioning

confidence: 99%

Iodine-mediated hydration of alkynes on keto-functionalized scaffolds: mechanistic insight and the regiospecific hydration of internal alkynes

Lee

Jones

Nkengbeza

et al. 2019

Beilstein J. Org. Chem.

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“…Prepared as for 15 from 4′-bromoacetophenone (0.50 g, 2.51 mmol) and benzaldehyde (0.27 g, 2.51 mmol) to yield the title compound 19 as light yellow crystals (0.72 g, 63%): mp: 103.26 °C (EtOH); 1 H NMR (600 MHz, CDCl 3 ) δ 7.92–7.87 (m, 2H), 7.82 (d, J = 15.7 Hz, 1H), 7.69–7.60 (m, 4H), 7.48 (d, J = 15.7 Hz, 1H), 7.44–7.40 (m, 3H) (Zhou et al 2016 ). Purity (HPLC): 98%.…”

Section: Methodsmentioning

confidence: 99%

C3 amino-substituted chalcone derivative with selective adenosine rA1 receptor affinity in the micromolar range

2020

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To identify novel adenosine receptor (AR) ligands based on the chalcone scaffold, herein the synthesis, characterization and in vitro and in silico evaluation of 33 chalcones ( 15 – 36 and 37 – 41 ) and structurally related compounds ( 42 – 47 ) are reported. These compounds were characterized by radioligand binding and GTP shift assays to determine the degree and type of binding affinity, respectively, against rat ( r ) A 1 and A 2A ARs. The chalcone derivatives 24 , 29 , 37 and 38 possessed selective A 1 affinity below 10 µM, and thus, are the most active compounds of the present series; compound 38 was the most potent selective A 1 AR antagonist ( K i ( r ) = 1.6 µM). The structure–affinity relationships (SAR) revealed that the NH 2 -group at position C3 of ring A of the chalcone scaffold played a key role in affinity, and also, the Br-atom at position C3′ on benzylidene ring B. Upon in vitro and in silico evaluation, the novel C3 amino-substituted chalcone derivative 38 —that contains an α,ß-unsaturated carbonyl system and easily allows structural modification—may possibly be a synthon in future drug discovery. Graphic abstract C3 amino-substituted chalcone derivative ( 38 ) with C3′ Br substitution on benzylidene ring B possesses selective adenosine r A 1 receptor affinity in micromolar range. Electronic supplementary material The online version of this article (10.1007/s11696-020-01414-9) contains supplementary material, which is available to authorized users.

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“…( E )- 1-Phenyl-3-(p-tolyl)prop-2-en-1-one ( 1p ) [ 56 ]. 1 H-NMR (CDCl 3 ): δ 8.07–7.99 (2H, m), 7.80 (1H, d, J = 15.6 Hz), 7.61–7.46 (6H, m), 7.24 (2H, t, J = 7.6 Hz), 2.40 (3H, s); 13 C-NMR (CDCl 3 ): δ 190.6, 144.9, 141.0, 138.3, 132.6, 132.1, 129.7, 128.5, 128.4, 128.4, 121.0, 21.49.…”

Section: Methodsmentioning

confidence: 99%

“…( E )- 1-(4-Fluorophenyl)-3-phenylprop-2-en-1-one ( 1t ) [ 56 ]. 1 H-NMR (CDCl 3 ): δ 8.06 (2H, dd, J = 8.7, 5.5 Hz), 7.82 (1H, d, J = 15.6 Hz), 7.63–7.61 (2H, m), 7.51 (1H, d, J = 15.6 Hz), 7.46–7.37 (3H, m), 7.17–7.13 (2H, m); 13 C-NMR (CDCl 3 ): δ 188.7, 165.5 (d, J C–F = 252.9 Hz), 144.9, 134.7, 134.4 (d, J C–F = 2.9 Hz), 131.0 (d, J C–F = 9.2 Hz), 130.5, 128.9, 128.4, 121.5, 115.7 (d, J C–F = 21.7).…”

Section: Methodsmentioning

confidence: 99%

Chalcone Derivatives Enhance ATP-Binding Cassette Transporters A1 in Human THP-1 Macrophages

et al. 2018

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Atherosclerosis is a process of imbalanced lipid metabolism in the vascular walls. The underlying pathology mainly involves the deposition of oxidized lipids in the endothelium and the accumulation of cholesterol in macrophages. Macrophages export excessive cholesterol (cholesterol efflux) through ATP-binding cassette transporter A1 (ABCA1) to counter the progression of atherosclerosis. We synthesized novel chalcone derivatives and assessed their effects and the underlying mechanisms on ABCA1 expression in macrophages. Human THP-1 macrophages were treated with synthetic chalcone derivatives for 24 h. In Western blot and flow cytometry analyses, a chalcone derivative, (E)-1-(3,4-diisopropoxyphenyl)-3-(4-isopropoxy-3-methoxyphenyl)prop- 2-en-1-one (1m), was observed to significantly enhance ABCA1 protein expression in THP-1 cells (10 µM, 24 h). Levels of mRNA of ABCA1 and liver X receptor alpha (LXRα) were quantified using a real-time quantitative polymerase chain reaction technique and were found to be significantly increased after treatment with the novel chalcone derivative 1m. Several microRNAs, including miR155, miR758, miR10b, miR145, miR33, and miR106b, which functionally inhibit ABCA1 expression were suppressed after treatment with 1m. Collectively, 1m increases ABCA1 expression in human THP-1 macrophages. The mechanisms involve the activation of the LXRα-ABCA1 pathway and suppression of certain microRNAs that regulate ABCA1 expression.

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Phosphorous Acid Promoted Hydration–Condensation of Aromatic Alkynes with Aldehydes Affording Chalcones in an Oil/Water Two-Phase System

Cited by 14 publications

References 2 publications

Iodine-mediated hydration of alkynes on keto-functionalized scaffolds: mechanistic insight and the regiospecific hydration of internal alkynes

Iodine-mediated hydration of alkynes on keto-functionalized scaffolds: mechanistic insight and the regiospecific hydration of internal alkynes

C3 amino-substituted chalcone derivative with selective adenosine rA1 receptor affinity in the micromolar range

Chalcone Derivatives Enhance ATP-Binding Cassette Transporters A1 in Human THP-1 Macrophages

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