Reaktionen mit 2.4‐disubstituierten Δ<sup>2</sup>‐Oxazolinonen‐(5)

Mustafa, Ahmed; Asker, Wafia; Harhash, Abdel Hamid; Abdin, T.; Zayed, E. M.

doi:10.1002/jlac.19687140115

Cited by 13 publications

(4 citation statements)

References 12 publications

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“…The oxazolones 1a – 1m shown in Figure 2 have been prepared by the classical Erlenmeyer–Plöchl method, 12 while the hippuric acids have been prepared by the Schotten–Baumann method. 13 Oxazolones 1a – 1d and 1f – 1h appear on SciFinder, 14 while 1e and 1i – 1m are new species.…”

Section: Resultsmentioning

confidence: 99%

Fluorescence Amplification of Unsaturated Oxazolones Using Palladium: Photophysical and Computational Studies

et al. 2023

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Weakly fluorescent (Z)-4-arylidene-5-(4H)-oxazolones (1), ΦPL < 0.1%, containing a variety of conjugated aromatic fragments and/or charged arylidene moieties, have been orthopalladated by reaction with Pd(OAc)2. The resulting dinuclear complexes (2) have the oxazolone ligands bonded as a C^N-chelate, restricting intramolecular motions involving the oxazolone. From 2, a variety of mononuclear derivatives, such as [Pd(C^N-oxazolone)(O2CCF3)(py)] (3), [Pd(C^N-oxazolone)(py)2](ClO4) (4), [Pd(C^N-oxazolone)(Cl)(py)] (5), and [Pd(C^N-oxazolone)(X)(NHC)] (6, 7), have been prepared and fully characterized. Most of complexes 3–6 are strongly fluorescent in solution in the range of wavelengths from green to yellow, with values of ΦPL up to 28% (4h), which are among the highest values of quantum yield ever reported for organometallic Pd complexes with bidentate ligands. This means that the introduction of the Pd in the oxazolone scaffold produces in some cases an amplification of the fluorescence of several orders of magnitude from the free ligand 1 to complexes 3–6. Systematic variations of the substituents of the oxazolones and the ancillary ligands show that the wavelength of emission is tuned by the nature of the oxazolone, while the quantum yield is deeply influenced by the change of ligands. TD-DFT studies of complexes 3–6 show a direct correlation between the participation of the Pd orbitals in the HOMO and the loss of emission through non-radiative pathways. This model allows the understanding of the amplification of the fluorescence and the future rational design of new organopalladium systems with improved properties.

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Section: Resultsmentioning

confidence: 99%

Fluorescence Amplification of Unsaturated Oxazolones Using Palladium: Photophysical and Computational Studies

et al. 2023

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“…4-((Z)-R-benzylidene)-2-((E)-styryl)oxazol-5(4H)-one (( 1)-( 7)) [11,16,36]: Cinnamoylglycine (2.0 g, 9.7 mmol), sodium acetate (0.69 g, 8.5 mmol), the corresponding aromatic aldehyde (11.5 mmol), and acetic anhydride (4.5 mL) were refluxed for 1 h. Following the removal of solvent, the residue was washed with cold ethanol and dried to give a yellow solid.…”

Section: Synthesis and Characterization Of Oxazolonesmentioning

confidence: 99%

“…We have added a styryl moiety to optimize the interaction of synthesized compounds with aromatic amino acids characteristic of the PAS and the access gorge. Compounds (1)-(4) were previously synthesized by Mustafa A., et al [16]. Compounds (1), (3), and (4) were recently synthetized using K 3 PO 4 as catalyst [11].…”

Section: Introductionmentioning

confidence: 99%

Inhibitory Activity of 4-Benzylidene Oxazolones Derivatives of Cinnamic Acid on Human Acetylcholinesterase and Cognitive Improvements in a Mouse Model

Ramírez-Ruiz,

Ávila-Cossío,

Estolano-Cobián

et al. 2023

Molecules

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We synthesized seven (Z)-benzylidene-2-(E)-styryloxazol-5(4H)-ones derivatives of cinnamic acid and evaluated the ability of these compounds to inhibit human acetylcholinesterase (hAChE). The most potent compound was evaluated for cognitive improvement in short-term memory. The seven compounds reversibly inhibited the hAChE between 51 and 75% at 300 μM, showed an affinity (Ki) from 2 to 198 μM, and an IC50 from 9 to 246 μM. Molecular docking studies revealed that all binding moieties are involved in the non-covalent interactions with hAChE for all compounds. In addition, in silico pharmacokinetic analysis was carried out to predict the compounds’ blood–brain barrier (BBB) permeability. The most potent inhibitor of hAChE significantly improved cognitive impairment in a modified Y-maze test (5 μmol/kg) and an Object Recognition Test (10 μmol/kg). Our results can help the rational design of hAChE inhibitors to work as potential candidates for treating cognitive disorders.

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“…Solvents and reagents were purchased from Sigma-Aldrich (USA), VWR (USA) or 38], and 1712 [21] were prepared according to procedures mentioned below, and their physical and spectral properties were confirmed.…”

Section: Chemical Synthesismentioning

confidence: 99%

Discovery, Optimization, and Cellular Activities of 2-(Aroylamino)cinnamamide Derivatives Against Colon Cancer

Omar¹,

El‐Araby²,

Abdelghany³

et al. 2020

Preprint

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Curcumin and trans-cinnamaldehyde are acrolein-based Michael acceptor compounds that are commonly found in domestic condiments, and known to cause cancer cell death via redox mechanisms. Based on the structural features of these compounds we designed and synthesized several 2-cinnamamido-N-substituted-cinnamamide (bis-cinnamamide) compounds. One of the derivatives, (Z)-2-[(E)-cinnamamido]-3-phenyl-N-propylacrylamide 1512 showed a moderate antiproliferative potency (HCT-116 cell line inhibition of 32.0 µM), good selectivity profile (no inhibition of normal cell lines), and proven cellular activities leading to apoptosis. SAR studies led to more than 10-fold increase in activity. Our most promising compound, [(Z)-3-(1H-indol-3-yl)-N-propyl-2-[(E)-3-(thien-2-yl)propenamido)propenamide] 4112 killed colon cancer cells at IC50 = 0.89 µM (Caco-2), 2.85 µM (HCT-116) and 1.65 µM (HT-29), while exhibiting much weaker potency on C-166 and BHK normal cell lines (IC50 = 71 µM and 77.6 µM, respectively). Cellular studies towards identifying the compounds mechanism of cytotoxic activities revealed that apoptotic induction occurs in part as a result of oxidative stress. Importantly, the compounds showed inhibition of cancer stem cells that are critical for maintaining the potential for self-renewal and stemness. The results presented here show discovery of covalently-acting Michael addition compounds that potently kill cancer cells by a defined mechanism, with minimal effect on normal noncancerous cell.

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Reaktionen mit 2.4‐disubstituierten Δ²‐Oxazolinonen‐(5)

Cited by 13 publications

References 12 publications

Fluorescence Amplification of Unsaturated Oxazolones Using Palladium: Photophysical and Computational Studies

Fluorescence Amplification of Unsaturated Oxazolones Using Palladium: Photophysical and Computational Studies

Inhibitory Activity of 4-Benzylidene Oxazolones Derivatives of Cinnamic Acid on Human Acetylcholinesterase and Cognitive Improvements in a Mouse Model

Discovery, Optimization, and Cellular Activities of 2-(Aroylamino)cinnamamide Derivatives Against Colon Cancer

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Reaktionen mit 2.4‐disubstituierten Δ2‐Oxazolinonen‐(5)

Cited by 13 publications

References 12 publications

Fluorescence Amplification of Unsaturated Oxazolones Using Palladium: Photophysical and Computational Studies

Fluorescence Amplification of Unsaturated Oxazolones Using Palladium: Photophysical and Computational Studies

Inhibitory Activity of 4-Benzylidene Oxazolones Derivatives of Cinnamic Acid on Human Acetylcholinesterase and Cognitive Improvements in a Mouse Model

Discovery, Optimization, and Cellular Activities of 2-(Aroylamino)cinnamamide Derivatives Against Colon Cancer

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Reaktionen mit 2.4‐disubstituierten Δ²‐Oxazolinonen‐(5)