NMR study of conformation and isomerization of aryl- and heteroarylaldehyde 4-tert-butylphenoxyacetylhydrazones

Syakaev, Victor V.; Podyachev, Sergey N.; Бузыкин, Б. И.; Latypov, Shamil K.; Habicher, Wolf D.; Коновалов, А. И.

doi:10.1016/j.molstruc.2005.11.018

Cited by 102 publications

(65 citation statements)

References 10 publications

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“…14,15 In our study, we obtained a crystal structure of 1 .EtOH (Scheme 2), which demonstrated that in the solid state, the imine of 1 exists in the E configuration and the N–C(O) existed as trans rotamers (C=O anti to the NH). In solution, the N–C(O) group of 1 interconverts between cis and trans rotamers (Scheme 2).…”

mentioning

confidence: 81%

Structure–Activity Studies of Divin: An Inhibitor of Bacterial Cell Division

Zhou

Eun²,

Guzei³

et al. 2013

ACS Med. Chem. Lett.

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We describe the synthesis and SAR studies of divin—a small molecule that blocks bacterial division by perturbing the assembly of proteins at the site of cell septation. The bacteriostatic mechanism of action of divin is distinct from other reported inhibitors of bacterial cell division and provides an opportunity for assessing the therapeutic value of a new class of antimicrobial agents. We demonstrate a convenient synthetic route to divin and its analogs, and describe compounds with a 10-fold increase in solubility and a 4-fold improvement in potency. Divin analogs produce a phenotype that is identical to divin, suggesting that their biological activity comes from a similar mechanism of action. Our studies indicate that the 2-hydroxynaphthalenyl hydrazide portion of divin is essential for its activity and that alterations and substitution to the benzimidazole ring can increase its potency. The SAR study provides a critical opportunity to isolate drug resistant mutants and synthesize photoaffinity probes to determine the cellular target and biomolecular mechanism of divin.

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mentioning

confidence: 81%

Structure–Activity Studies of Divin: An Inhibitor of Bacterial Cell Division

Zhou

Eun²,

Guzei³

et al. 2013

ACS Med. Chem. Lett.

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“…Several studies using 1 H NMR spectroscopy have shown that NAHs of aromatic and alkyl carbonyl compounds show different patterns depending on the polarization and electron donation properties of solvents such as CDCl 3 and DMSO [29]. In deuterated chloroform solution, 1 H NMR spectra of NAHs 1-6 displayed doubled signals, indicating the presence of two forms assigned to cis-and trans-amide conformers in different proportions ( Table 3).…”

Section: Methodsmentioning

confidence: 99%

“…In the literature [29], it is well established that hydrazones can exist as cis/trans conformers about the C(O)-N bond and E/Z geometrical isomers with respect to the C=N double bond as shown in Fig. 1.…”

Section: Characterizationmentioning

confidence: 99%

Synthesis, Characterization, and Conformational Study of Acylhydrazones of α,β‐Unsaturated Aldehydes

Hamzi

Barhoumi‐Slimi²,

Abidi

2016

Heteroatom Chemistry

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“…This signal for the cis conformers of acyl hydrazones is shifted downfield by 5-6 ppm compared to an analogous signal for the trans conformers 7,9 and appears at δ 170 for the acylhydrazones described in Ref. 7. Therefore, acylhydrazone 4″ is a 3.3 : 1 mixture of the cis,Z and trans,Z isomers.…”

Section: Methodsmentioning

confidence: 62%

Isatin acylhydrazones with sterically hindered phenolic fragments: synthesis and structures

et al. 2009

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Isatin acylhydrazones with sterically hindered phenolic fragments were obtained. Their structures were determined using 1D and 2D 1 H and 13 C NMR spectroscopy and X ray diffraction. The products synthesized by condensation of isatin and 1 (3,5 di tert butyl 4 hydroxybenzyl) 1H indole 2,3 dione with 3 (3,5 di tert butyl 4 hydroxyphenyl)propiono hydrazide exist as E and Z isomers about the C=N bond. E-Z isomerization takes place in boiling ethanol. The E isomer of the condensation product from isatin and 3 (3,5 di tert butyl 4 hydroxyphenyl)propionohydrazide was structurally characterized using X ray diffraction: this isomer is a cis conformer about the amide group and has a E configuration about the N-N bond. According to data on the concentration dependence of the signals for the NH protons in the 1 H NMR spectra, the acylhydrazones obtained are stabilized in solution by intra and intermolecular hydrogen bonding.

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NMR study of conformation and isomerization of aryl- and heteroarylaldehyde 4-tert-butylphenoxyacetylhydrazones

Cited by 102 publications

References 10 publications

Structure–Activity Studies of Divin: An Inhibitor of Bacterial Cell Division

Structure–Activity Studies of Divin: An Inhibitor of Bacterial Cell Division

Synthesis, Characterization, and Conformational Study of Acylhydrazones of α,β‐Unsaturated Aldehydes

Isatin acylhydrazones with sterically hindered phenolic fragments: synthesis and structures

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