The preparation of (4<i>H</i>)-imidazol-4-ones and their application in the total synthesis of natural products

Keel, Katarina L.; Tepe, Jetze J.

doi:10.1039/d0qo00764a

Cited by 19 publications

(28 citation statements)

References 192 publications

(230 reference statements)

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“…This effect is mimicked in several recent studies, which focused on numerous conformationally unrestricted and restricted GFP‐like chromophores [12] . Various structurally locked analogues have been synthesized and studied recently to establish strategies for the recovery of the fluorescent intensity in small molecular GFP fluorophore analogues [16–18] …”

Section: Introductionmentioning

confidence: 85%

Synthesis and Fluorescence Mechanism of the Aminoimidazolone Analogues of the Green Fluorescent Protein: Towards Advanced Dyes with Enhanced Stokes Shift, Quantum Yield and Two‐Photon Absorption

et al. 2021

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Novel small‐molecular analogues the green fluorescence protein (GFP) chromophore were synthesised to expand and improve this fluorophore family and to deepen the understanding of their fluorescence mechanism. The introduction of an aminophenyl substituent and the repositioning of the hydroxyl group, to enable strong intramolecular hydrogen bonding, not only enhanced fluorescence emission but also resulted in an increased Stokes shift and a considerable redshift. Experimental and computational results described dual fluorescence involving both excited‐state intramolecular proton transfer and internal charge transfer (ESIPT‐ICT) mechanisms. Screening of the pH and the solvent medium revealed a complicated equilibrium involving hydrogen bonding, protonation and deprotonation that influences the absorption and emission spectra. Further improvement of the photophysical properties via the systematic variation of dialkylamino substituents at a single position of the chromophore led to a two‐orders of magnitude enhancement in the quantum yields. In addition, the novel compounds also have significant two‐photon absorption, which widens the possibilities for applications in the field of bioimaging.

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Section: Introductionmentioning

confidence: 85%

Synthesis and Fluorescence Mechanism of the Aminoimidazolone Analogues of the Green Fluorescent Protein: Towards Advanced Dyes with Enhanced Stokes Shift, Quantum Yield and Two‐Photon Absorption

et al. 2021

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“…Using this catalyst, the authors successfully accomplished the aerobic dehydrocyclization of neighboring diols and amidines to access various imidazolone structures. Imidazolones are a class of valuable compounds found in numerous natural and biomedical products [41,42].…”

Section: Scheme 4 Synthesis Of Quinazolinones Via An Acceptorless Coupling Of O-aminobenzamidesmentioning

confidence: 99%

Advances in Green Catalysis for the Synthesis of Medicinally Relevant N-Heterocycles

et al. 2021

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N-heterocycles, both saturated and unsaturated, are ubiquitous biologically active molecules that are extremely appealing scaffolds in drug discovery programs. Although classical synthetic methods have been developed to access many relevant N-heterocyclic scaffolds, representing well-established and reliable routes, some do not meet the needs of sustainability. In this context, several advances have been made towards the sustainable synthesis of N-heterocycles. This review focuses on the most recent examples from the last five years of catalytic synthesis of several heterocyclic compounds of medicinal relevance. Thus, the synthesis of isoindoloquinazolines, quinazolines and azaindoles, among others, are covered. The synthetic methods selected include the use of homogeneous and heterogeneous catalysts and the use of alternative and sustainable methods such as, for example, metal-catalyzed acceptorless coupling and one-pot reactions. The green aspects of the individual synthetic approaches are highlighted, and the scope of each methodology is described.

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“…Functionalized imidazolones have been recognized due to their potent therapeutic effect, including sedative, anticonvulsant, antibacterial, antifungal, antihistamine, antihypertensive, anti-inflammatory and anthelmintic activities. [1] Among the biologically significant derivatives of imidazolones, there are already known sulfonate ester-containing imidazolone [12] and N-arylazo-imidazolone derivatives [13] with antibacterial and significant antifungal properties, imidazolone isomers depending on the location of the carbonyl group (4H)imidazol-4-ones and imidazol-2-ones and imidazol-4-ones used in medicine and agriculture, [14] 2-substituted phenyl-3-(phenyl-(substituted amino) methyl amino)-5-(3',4',5'-trimethoxy benzylidene)-3,5-dihydro-imidazol-4-ones with bactericidal activity, [15] 6-nitro-1,3-bis(2-phenoxyethyl)-1,3-dihydro-2H-benzimidazol-2-ones with antimicrobial including antituberculosis activity, [16] 2,4-diaryl-5-4H-imidazolones with anti-inflammatory activities, [17] new chalcone-imidazolone conjugates with anticancer activity, [18] 3-{(4-chlorophenyl)methylidene]amino}-2phenyl-5-(thiophen-2-ylmethylidene)-3,5-dihydro-4H-imidazol-4-ones with best antioxidant activity. [19] A series of new 5-imino-4-thioxo-2-imidazolidinone derivatives with various alkylated and halogenated aromatic substituents showed significant antibacterial and antifungal activities.…”

Section: Introductionmentioning

confidence: 99%

In Silico, in Vitro and in Vivo Study of Substituted Imidazolidinone Sulfonamides as Antibacterial Agents

Hodyna,

Kovalishyn,

Kachaeva

et al. 2023

Chemistry & Biodiversity

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New substituted imidazolidinone sulfonamides have been developed using a rational drug design strategy. Predictive QSAR models for the search of new antibacterials were created using the OCHEM platform. Regression models were applied to verify a virtual chemical library of new imidazolidinone derivatives designed to have antibacterial activity. A number of substituted imidazolidinone sulfonamides as effective antibacterial agents were identified by QSAR prediction, synthesized and characterized by spectral and elemental, and tested in vitro. Six studied compounds have shown the highest in vitro antibacterial activity against Gram‐negative E. coli and Gram‐positive S. aureus multidrug‐resistant strains. The in vivo acute toxicity of these imidazolidinone sulfonamides based on the LC50 value ranged from 16.01 to 44.35 mg/L (slightly toxic compounds class). The results of molecular docking suggest that the antibacterial mechanism of the compounds can be associated with the inhibition of post‐translational modification processes of bacterial peptides and proteins.

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The preparation of (4H)-imidazol-4-ones and their application in the total synthesis of natural products

Abstract: The first review article summarizing known methodologies for the preparation of (4H)-imidazol-4-ones and their application in the total synthesis of imidazol-4-one containing natural products.

Cited by 19 publications

References 192 publications

Synthesis and Fluorescence Mechanism of the Aminoimidazolone Analogues of the Green Fluorescent Protein: Towards Advanced Dyes with Enhanced Stokes Shift, Quantum Yield and Two‐Photon Absorption

Synthesis and Fluorescence Mechanism of the Aminoimidazolone Analogues of the Green Fluorescent Protein: Towards Advanced Dyes with Enhanced Stokes Shift, Quantum Yield and Two‐Photon Absorption

Advances in Green Catalysis for the Synthesis of Medicinally Relevant N-Heterocycles

In Silico, in Vitro and in Vivo Study of Substituted Imidazolidinone Sulfonamides as Antibacterial Agents

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