Effect of substituents in novel bioactive tavaborole derivatives on the intermolecular interaction hierarchy

Dąbrowska, A.; Adamczyk‐Woźniak, Agnieszka; Madura, Izabela D.

doi:10.1039/d2ce00279e

Cited by 3 publications

(2 citation statements)

References 44 publications

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“…Recently, 5-fluoro-3-morpholin-4-yl-2,1-benzoxaborol-1(3H)-ol and 5-fluoro-3-thiomorpholin-4-yl-2,1-benzoxaborol-1(3H)-ol have been synthesized, and their crystal structures were determined and compared with the parent tavaborole and nonfluorinated benzoxaborole analogs [ 60 ]. It was found that the presence of the fluorine atom reduces both the molecular dipole moment, as well as the negative potential at the oxygen atom, in the heterocyclic ring.…”

Section: Crystal Structuresmentioning

confidence: 99%

Merging Electron Deficient Boronic Centers with Electron-Withdrawing Fluorine Substituents Results in Unique Properties of Fluorinated Phenylboronic Compounds

Adamczyk‐Woźniak

Sporzyński

2022

Molecules

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Fluorinated boron species are a very important group of organoboron compounds used first of all as receptors of important bioanalytes, as well as biologically active substances, including Tavaborole as an antifungal drug. The presence of substituents containing fluorine atoms increases the acidity of boronic compounds, which is crucial from the point of view of their interactions with analytes or certain pathogen’s enzymes. The review discusses the electron acceptor properties of fluorinated boronic species using both the acidity constant (pKa) and acceptor number (AN) in connection with their structural parameters. The NMR spectroscopic data are also presented, with particular emphasis on 19F resonance due to the wide range of information that can be obtained from this technique. Equilibria in solutions, such as the dehydration of boronic acid to form boroxines and their esterification or cyclization with the formation of 3-hydroxyl benzoxaboroles, are discussed. The results of the latest research on the biological activity of boronic compounds by experimental in vitro methods and theoretical calculations using docking studies are also discussed.

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Section: Crystal Structuresmentioning

confidence: 99%

Merging Electron Deficient Boronic Centers with Electron-Withdrawing Fluorine Substituents Results in Unique Properties of Fluorinated Phenylboronic Compounds

Adamczyk‐Woźniak

Sporzyński

2022

Molecules

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“…Derivatives bearing alkyl, 13,21,22 aryl, [23][24][25][26][27] heteroaryl 28 or heterocyclic (morpholine, thiomorpholine, diazine etc.) 19,[29][30][31][32][33] groups at the C3 position were also structurally characterized. It is also worth noting that benzoxaboroles were used as co-crystal components with 4,4′-bipyridine and related HB acceptors.…”

Section: Introductionmentioning

confidence: 99%

Exploring the effect of substitution patterns on the symmetry of hydrogen-bonded supramolecular motifs in functionalized benzosiloxaboroles

Durka,

Zuba,

Marek-Urban

et al. 2023

CrystEngComm

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Activity of Organoboron Compounds against Biofilm-Forming Pathogens

Konaklieva,

Plotkin

2024

Antibiotics

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Bacteria have evolved and continue to change in response to environmental stressors including antibiotics. Antibiotic resistance and the ability to form biofilms are inextricably linked, requiring the continuous search for alternative compounds to antibiotics that affect biofilm formation. One of the latest drug classes is boron-containing compounds. Over the last several decades, boron has emerged as a prominent element in the field of medicinal chemistry, which has led to an increasing number of boron-containing compounds being considered as potential drugs. The focus of this review is on the developments in boron-containing organic compounds (BOCs) as antimicrobial/anti-biofilm probes and agents.

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Effect of substituents in novel bioactive tavaborole derivatives on the intermolecular interaction hierarchy

Cited by 3 publications

References 44 publications

Merging Electron Deficient Boronic Centers with Electron-Withdrawing Fluorine Substituents Results in Unique Properties of Fluorinated Phenylboronic Compounds

Merging Electron Deficient Boronic Centers with Electron-Withdrawing Fluorine Substituents Results in Unique Properties of Fluorinated Phenylboronic Compounds

Exploring the effect of substitution patterns on the symmetry of hydrogen-bonded supramolecular motifs in functionalized benzosiloxaboroles

Activity of Organoboron Compounds against Biofilm-Forming Pathogens

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