Fluoroimidazoles and their Heteroannelated Derivatives: Synthesis and Properties (Review)

Lipunova, G. N.; Носова, Э. В.; Charushin, Valery N.

doi:10.1007/s10593-014-1422-6

Cited by 8 publications

(3 citation statements)

References 47 publications

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“…An accelerated and improved one-pot synthesis of 2,4,6-triphenyl-1Himidazoles (46 a-o) was carried out by the reaction of benzyl (44), aromatic aldehydes (45), and ammonium acetate (NH4OAc) in the presence of ZnO. The indicated route of synthesis represented an environmentally friendly, sparing reaction, leading within a short time to new imidazole derivatives with the yield of 60-93% [40].…”

Section: Synthesis Of Biologically Active Imidazole Derivativesmentioning

confidence: 99%

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PROSPECTS FOR THE CHEMISTRY OF IMIDAZOLE DERIVATIVES (Review)

Kaldybayeva¹,

Malmakova²,

Yu³

et al. 2022

Chem. J. of Kaz.

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The problem of creating new effective domestic pharmacological preparations, including the development of the methods for obtaining biologically active substances in compliance with the “green chemistry” principles, are among the priority areas for the development of chemical science. The choice of an initial molecule, which carries the potential of biological activity, is the guarantor of a successful experimental search. Imidazole derivatives occupy a unique place in the medicinal chemistry. An imidazole cycle is part of the natural compounds such as histamine, biotin, some alkaloids and nucleic acids, and is a structural fragment of medicinal preparations. The goalof the present review is to analyze the publications on the chemistry of imidazole derivatives with an emphasis on the methods of obtaining biologically active and other practically useful molecules with an obligatory imidazole cycle. The objects of the study:imidazole derivatives. The examples of the routes of synthesizing imidazole derivatives, as well as the compounds of interest for the medicinal chemistry, agriculture, and other fields, which have been published in the scientific and technical literature since 2000, have been presented. Conclusion.The studies in the field of searching for new highly effective preparations among imidazole derivatives are relevant and promising. The most important stage in this search is the directed synthesis of the substances with the specified, practically useful properties. The range of new practically useful substances in the series of imidazole derivatives has been significantly expanded and replenished thanks to the modern modifications of the classical methods of their obtaining.

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Section: Synthesis Of Biologically Active Imidazole Derivativesmentioning

confidence: 99%

“…A review of the chemistry of fluoroimidazoles and their heteroannelated derivatives was published in 2014 by Nossova et al [44]. The review considered the syntheses, chemical properties, biological significance, and other properties of the fluoroimidazole class of heterocycles.…”

Section: Synthesis Of Biologically Active Imidazole Derivativesmentioning

confidence: 99%

PROSPECTS FOR THE CHEMISTRY OF IMIDAZOLE DERIVATIVES (Review)

Kaldybayeva¹,

Malmakova²,

Yu³

et al. 2022

Chem. J. of Kaz.

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“…Multiple methods for the synthesis of fluorohistidines have been developed 6 7 8 9 10 . The ability to incorporate these analogues of histidine into proteins has facilitated mechanistic studies of proton transfer (discussed below) and characterization of protein structure using 19 F-NMR 11 12 13 14 15 16 17 18 19 20 .…”

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confidence: 99%

The Biophysical Probes 2-fluorohistidine and 4-fluorohistidine: Spectroscopic Signatures and Molecular Properties

Kasireddy

Ellis

Bann

et al. 2017

Sci Rep

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Fluorinated amino acids serve as valuable biological probes, by reporting on local protein structure and dynamics through 19F NMR chemical shifts. 2-fluorohistidine and 4-fluorohistidine, studied here with DFT methods, have even more capabilities for biophysical studies, as their altered pKa values, relative to histidine, allow for studies of the role of proton transfer and tautomeric state in enzymatic mechanisms. Considering the two tautomeric forms of histidine, it was found that 2-fluorohistidine primarily forms the common (for histidine) τ-tautomer at neutral pH, while 4-fluorohistidine exclusively forms the less common π-tautomer. This suggests the two isomers of fluorohistidine can also serve as probes of tautomeric form within biomolecules, both by monitoring NMR chemical shifts and by potential perturbation of the tautomeric equilibrium within biomolecules. Fluorine also enables assignment of tautomeric states in crystal structures. The differences in experimental pKa values between the isomers was found to arise from solvation effects, providing insight into the polarization and molecular properties of each isomer. Results also encompass 13C and 19F NMR chemical shifts, from both tautomers of 2-fluorohistidine and 4-fluorohistidine in a number of different environments. This work can serve as a guide for interpretation of spectroscopic results in biophysical studies employing 2-fluorohistidine and 4-fluorohistidine.

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