242. Chalcones and related compounds. Part IV. Addition of hydrogen cyanide to chalcones

Davey, Wheeler P.; Tivey, D. J.

doi:10.1039/jr9580001230

Cited by 47 publications

(27 citation statements)

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“…Preparation of 4 was done according to a previously described method, providing the chalcone (2.36 g, 88%). mp 86.5–88.5°C (from ethanol : water [3:1]) (lit., 88°C).…”

Section: Synthesis and Structural Elucidationmentioning

confidence: 99%

Absolute configuration and biological profile of pyrazoline enantiomers as MAO inhibitory activity

et al. 2018

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A new racemic pyrazoline derivative was synthesized and resolved to its enantiomers using analytic and semipreparative high‐pressure liquid chromatography. The absolute configuration of both fractions was established using vibrational circular dichroism. The in vitro monoamine oxidase (MAO) inhibitory profiles were evaluated for the racemate and both enantiomers separately for the two isoforms of the enzyme. The racemic compound and both enantiomers were found to inhibit hMAO‐A selectively and competitively. In particular, the R enantiomer was detected as an exceptionally potent and a selective MAO‐A inhibitor (Ki = 0.85 × 10−3 ± 0.05 × 10−3 μM and SI: 2.35 × 10−5), whereas S was determined as poorer compound than R in terms of Ki and SI (0.184 ± 0.007 and 0.001). The selectivity of the enantiomers was explained by molecular modeling docking studies based on the PDB enzymatic models of MAO isoforms.

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“…Preparation of 4 was done according to a previously described method, providing the chalcone (2.36 g, 88%). mp 86.5–88.5°C (from ethanol : water [3:1]) (lit., 88°C).…”

Section: Synthesis and Structural Elucidationmentioning

confidence: 99%

Absolute configuration and biological profile of pyrazoline enantiomers as MAO inhibitory activity

et al. 2018

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“…The general synthetic strategy employed to prepare the bischalcone derivatives is based on the Claisen-Schmidt condensation (Davey and Tivey, 1958;Lyle and Paradis, 1955). Firstly, the reaction between benzaldehyde and 1,4-diacetylbenzene in the presence of NaOH as a base using various solvents including water, which known as an attractive medium for many organic reactions, was considered at room temperature.…”

Section: Synthesismentioning

confidence: 99%

“…Chemically, chalcones consist of an open chain in which the two aromatic rings are joined by a three-carbon unsaturated carbonyl system. Chalcones can be easily obtained through the Claisen-Schmidt condensation of benzaldehyde and acetophenone using either basic or acidic catalysts (Davey and Tivey, 1958;Lyle and Paradis, 1955). These compounds are not only a segment of biologically important but also a versatile intermediate for the synthesis of heterocyclic compounds (Nagaraj and Reddy, 2008;Bhat et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and antimicrobial activities of some novel bis-chalcones

2011

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A series of novel bis-chalcones 3a-n were synthesized in excellent yields by condensation reaction of 1,4-diacetylbenzene with various aldehydes in ethanol 96% and aqueous NaOH at room temperature. All compounds were characterized by IR, 1 H and 13 C NMR, UV spectroscopy and elemental analysis. The antimicrobial activities of synthesized compounds were also evaluated. The most of these compounds exhibited a good activity against Staphylococcus aureus, Escherichia coli and Candida albicans microorganisms. Some of them showed significant activities.

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“…Claisen-Schmidt condensation [18][19][20][21][22][23] of chalcones by conventional method involves addition of equimolar quantities (0.001 mol) of 2-acetyl-5-chloro-thiophene and respective aldehydes (0.001 mol) [5]. …”

Section: Conventional Methodsmentioning

confidence: 99%

A comparative study on synthesis of some novel α,β-unsaturated carbonyl derivatives and their antioxidant potential

et al. 2012

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242. Chalcones and related compounds. Part IV. Addition of hydrogen cyanide to chalcones

Cited by 47 publications

References 0 publications

Absolute configuration and biological profile of pyrazoline enantiomers as MAO inhibitory activity

Absolute configuration and biological profile of pyrazoline enantiomers as MAO inhibitory activity

Synthesis, characterization and antimicrobial activities of some novel bis-chalcones

A comparative study on synthesis of some novel α,β-unsaturated carbonyl derivatives and their antioxidant potential

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