Synthesis and Study of 1-Aryl-1<b>
                     <i>H</i>
                  </b>-4,5-dihydroimidazoles

Perillo, Isabel A.; Caterina, María Cristina; Lopez, J. M. Martinez; Salerno, Alejandra

doi:10.1055/s-2004-816011

Cited by 24 publications

(13 citation statements)

References 12 publications

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“…The contribution of canonic structures III is revealed in the shielding observed for 1-aryl ortho and para hydrogens. However, this effect is less than that previously observed in N -aryl-ethylenediamines [ 19 ], since the N1 lone electron pair is also involved in electron delocalization of amidine system ( I ↔ II ).…”

Section: Resultscontrasting

confidence: 62%

“…J values are given in Hertz (Hz). Compounds 1 , 2 , 5 and 9 [ 17 ]; 3 , 8 and 13 [ 12 ]; 4 , 6 and 10 [ 18 ]; 7 [ 14 ]; 12 [ 22 ] and 14 [ 19 ] were prepared following literature procedures.…”

Section: Methodsmentioning

confidence: 99%

“…Imidazoline nuclei were also employed as a source of carbon units in transfer reactions [ 15 , 16 ]. N -Alkyl substituted compounds have been extensively investigated while the N -aryl derivatives have been less studied, with the latest reports on the latter coming mostly from our laboratories [ 12 , 13 , 14 , 17 , 18 , 19 ]. Spectroscopic analysis is a suitable method to throw light upon electronic perturbations inherent to a system and to exhibit its structural features.…”

Section: Introductionmentioning

confidence: 99%

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1H- and 13C-NMR Analysis of a Series of 1,2-Diaryl-1H-4,5-dihydroimidazoles

Salerno¹,

Perillo²

2005

Molecules

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An analysis of the 1H- and 13C-NMR spectra of a series of 1,2-diaryl-1H-4,5-dihydroimidazoles and comparisons with 4,5-dihydroimidazoles having different substitution patterns are presented. The influence of different 1-aryl and 2-aryl group substituents on spectroscopic parameters of the heterocyclic ring and on the contributions of possible mesomeric structures in the system was determined. Spectroscopic features are coherent with the presence of two conjugated systems (Ar1-N and Ar2-C=N) which compete with the delocalization characteristics of the amidine system.

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Section: Resultscontrasting

confidence: 62%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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1H- and 13C-NMR Analysis of a Series of 1,2-Diaryl-1H-4,5-dihydroimidazoles

Salerno¹,

Perillo²

2005

Molecules

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“…From a chemical point of view, they are synthetic intermediates in the preparation of diazole derivatives8–13 and acyclic compounds 13–16. Imidazoline nuclei were also employed as a source of carbon units in transfer reactions 16–20. Particularly, the isomeric series arising from the linking between furan and imidazole rings through CC or CN bonds, which are known as furylimidazoles, are of great industrial and/or biological interest 21.…”

Section: Introductionmentioning

confidence: 99%

Structural and vibrational study of 2‐(2′‐ furyl)‐4,5‐1H‐dihydroimidazole

Zinczuk

Ledesma

Brandán

et al. 2009

J of Physical Organic Chem

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In this study 2-(2(-furyl)-4,5-1H-dihydroimidazole (1) was prepared and then characterized by infrared, Raman, and multidimensional nuclear magnetic resonance (NMR) spectroscopies. The crystal and molecular structures of 1 were determined by X-ray diffraction methods. The density functional theory (DFT) and second-order Møller-Plesset theory (MP2) with Pople's basis set show that there are two conformers for the title molecule that have been theoretically determined in the gas phase, and that only one of them, conformer I, is present in the solid phase. NMR spectra observed for 1 were successfully compared with the calculated chemical shifts at the B3LYP/6-311RRG ** level theorized for this conformer. The harmonic vibrational frequencies for the optimized geometry of the latter conformer were calculated at the B3LYP/6-311RRG ** level in the approximation of the isolated molecule. For a complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulaý s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones.

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“…The 3,4-dichlorophenyl-1,2-ethanediamine and the corresponding propyldiamine linkers 33 and 34 were prepared by refluxing excess 3,4-dichloroaniline ( 32 ) with the corresponding bromoalkyl hydrobromide 54. Mitsunobu conditions with 3,4-dichlorophenol ( 35 ) and N -Bocethanolamine followed by TFA deprotection gave amine 37 55.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, structural activity-relationships, and biological evaluation of novel amide-based allosteric binding site antagonists in NR1A/NR2B N-methyl-d-aspartate receptors☆

Mosley

Myers

Murray

et al. 2009

Bioorganic & Medicinal Chemistry

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The synthesis and structure–activity relationship analysis of a novel class of amide-based biaryl NR2B-selective NMDA receptor antagonists are presented. Some of the studied compounds are potent, selective, non-competitive, and voltage-independent antagonists of NR2B-containing NMDA receptors. Like the founding member of this class of antagonists (ifenprodil), several interesting compounds of the series bind to the amino terminal domain of the NR2B subunit to inhibit function. Analogue potency is modu-lated by linker length, flexibility, and hydrogen bonding opportunities. However, unlike previously described classes of NR2B-selective NMDA antagonists that exhibit off-target activity at a variety of monoamine receptors, the compounds described herein show much diminished effects against the hERG channel and α1-adrenergic receptors. Selections of the compounds discussed have acceptable half-lives in vivo and are predicted to permeate the blood–brain barrier. These data together suggest that masking charged atoms on the linker region of NR2B-selective antagonists can decrease undesirable side effects while still maintaining on-target potency.

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Synthesis and Study of 1-Aryl-1 H -4,5-dihydroimidazoles

Cited by 24 publications

References 12 publications

1H- and 13C-NMR Analysis of a Series of 1,2-Diaryl-1H-4,5-dihydroimidazoles

1H- and 13C-NMR Analysis of a Series of 1,2-Diaryl-1H-4,5-dihydroimidazoles

Structural and vibrational study of 2‐(2′‐ furyl)‐4,5‐1H‐dihydroimidazole

Synthesis, structural activity-relationships, and biological evaluation of novel amide-based allosteric binding site antagonists in NR1A/NR2B N-methyl-d-aspartate receptors☆

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