Structure and properties of phosphonium ylides-betaines, derivatives of 2-phenyl-2-oxazolin-5-one and its thio- and seleno-analogues

Meervelt, Luc Van; Schuerman, Geertrui; Brovarets, V. S.; Мищенко, Николай Иванович; Romanenko, E. A.; Drach, B. S.

doi:10.1016/0040-4020(94)01041-w

Cited by 10 publications

(4 citation statements)

References 3 publications

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“…Oxazoles 1–17 were synthesized according to the known methods (Abdurakhmanova, Pil’o, Kondratyuk, Golovchenko, & Brovarets, 2017; Brovarets, Vydzhak, Pil'o, Zyuz, & Drach, 2001; Van Meervelt et al, 1995) from the starting amides and trichloroacetaldehyde ( Schema 1 ). Obtained N ‐(2,2,2‐trichloro‐1‐hydroxyethyl)amides were treated with thionyl chloride to form N ‐(1,2,2,2‐tetrachloroethyl)amides.…”

Section: Resultsmentioning

confidence: 99%

In silico and in vitro studies of a number PILs as new antibacterials against MDR clinical isolate Acinetobacter baumannii

et al. 2020

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QSAR analysis of a set of previously synthesized phosphonium ionic liquids (PILs) tested against Gram-negative multidrug-resistant clinical isolate Acinetobacter baumannii was done using the Online Chemical Modeling Environment (OCHEM). To overcome the problem of overfitting due to descriptor selection, fivefold cross-validation with variable selection in each step of the model development was applied.The predictive ability of the classification models was tested by cross-validation, giving balanced accuracies (BA) of 76%-82%. The validation of the models using an external test set proved that the models can be used to predict the activity of newly designed compounds with a reasonable accuracy within the applicability domain (BA = 83%-89%). The models were applied to screen a virtual chemical library with expected activity of compounds against MDR Acinetobacter baumannii. The eighteen most promising compounds were identified, synthesized, and tested. Biological testing of compounds was performed using the disk diffusion method in Mueller-Hinton agar. All tested molecules demonstrated high anti-A. baumannii activity and different toxicity levels. The developed classification SAR models are freely available online at http://ochem.eu/artic le/113921 and could be used by scientists for design of new more effective antibiotics. K E Y W O R D SAcinetobacter baumanii, antibacterial activity, machine learning, OCHEM, phosphonium ionic liquids

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Section: Resultsmentioning

confidence: 99%

In silico and in vitro studies of a number PILs as new antibacterials against MDR clinical isolate Acinetobacter baumannii

et al. 2020

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“…It is noted that the three phenyl substituents at the phosphorus atom do not conjugate with the oxazole cycle and their -orbitals should generate own conjugated systems. Therefore, let us first compare the MOs in the simplest molecule (1b) and the reference molecule (2). After this, we have considered the influence of the phenyl substituent (1f) and the lengthening of the chain, and finally the effects of the introduction of chlorine atoms and the nitro group have been analyzed.…”

Section: Delocalized and Local Mosmentioning

confidence: 99%

“…1 So, it has resulted that the oxazole derivatives containing both positively charged PPh3 group and, simultaneously, the exocyclic mono-coordinated oxygen or sulfur/selenium atom, bearing the negative charge formally; their general formulae can be presented by one neutral and two betainic structures: I-III, 2 as it is shown in The chemical constitution and some physical properties of 2-phenyl-2-oxazolin-5-one with X = O, S, Se were studied in details; so, it was shown that contribution of structure III with the separated charges decreases in the order, O > S > Se, whereas the dipole momentum increases regularly.…”

Section: Introductionmentioning

confidence: 99%

“…4 This paper incorporates the results of the spectral and quantumchemical investigation of the electronic and spectral properties of phosphonium ylides and their sensitivity upon introduction of the simplest non-conjugated and conjugated substituents.A series of compounds, derivatives of phosphonium ylides of oxazole (1) has been studied ( Figure 2). The reference virtual compound (2) was chosen as a model one for comparison with (1) in quantum-chemical calculations. Phosphonium ylides (1) were obtained from corresponding phosphonium salts (4a-4l).…”

Section: Introductionmentioning

confidence: 99%

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Electronic and spectral properties of phosphonium ylides-betaines, derivatives of 2 oxazoline-5-one with conjugated and non-conjugated substituents

Броварец

Holovchenko

Naumenko

et al. 2017

ECB

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The spectral and quantum-chemical studies of phosphonium ylides derivatives of 2-oxazoline-5-one with both conjugated and nonconjugated substituents were performed. It was found that considerable positive charge is located at phosphorus atom, whereas the substantial negative charge is fixed at sulphur atom. It has been found from the calculations and 13 C NMR spectral data that introducing of the non-conjugated and conjugated substituents in the position 2 of the oxazole cycle in thiaphosphonium ylides causes only small change in the molecular equilibrium geometry and in charge distribution in oxazole moiety, whereas spectral characteristics of substituted derivatives are very sensitive to the nature of the lowest electron transitions which reflects in changes of their absorption maxima. * Corresponding AuthorFax: +38044-573-25-52 E-Mail: brovarets@bpci.kiev.ua [a]

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Synthesis and Structure of Pd and Pt Complexes with Doubly Stabilized Phosphorus Ylides

et al. 2006

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The doubly stabilized P‐ylide ligands Ph3P=C(CO2Me)C(=S)N(H)Ph (L1), Ph3P=C(CN)C(=S)N(H)Ph (L2), and Ph3P=C(CN)–[(E)‐C(CO2Me)=CH(CO2Me)] (L3) have been prepared and fully characterized. The X‐ray structures of L1 and L2 are reported. The reactivity of L1, L2, and L3 towards cationic PdII and PtII precursors with two vacant coordination sites has been studied. Adducts of general formula [M(CX)(Ln)]ClO4, [M(CX)(Ln)2]ClO4, and [M(μ‐Ln)(CX)]2(ClO4)2 (CX = ancillary ligands) were obtained. The ylides Ln coordinate to the metal center through their heteroatoms (O, N, S), while the C bonding of Ln has not been observed in any of the cases studied. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Structure and properties of phosphonium ylides-betaines, derivatives of 2-phenyl-2-oxazolin-5-one and its thio- and seleno-analogues

Cited by 10 publications

References 3 publications

In silico and in vitro studies of a number PILs as new antibacterials against MDR clinical isolate Acinetobacter baumannii

In silico and in vitro studies of a number PILs as new antibacterials against MDR clinical isolate Acinetobacter baumannii

Electronic and spectral properties of phosphonium ylides-betaines, derivatives of 2 oxazoline-5-one with conjugated and non-conjugated substituents

Synthesis and Structure of Pd and Pt Complexes with Doubly Stabilized Phosphorus Ylides

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