Changes in the hydrogen bonding pattern in ferrocene peptides

Appoh, Francis E.; Sutherland, Todd C.; Kraatz, Heinz‐Bernhard

doi:10.1016/j.jorganchem.2004.04.017

Cited by 48 publications

(37 citation statements)

References 49 publications

(51 reference statements)

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“…Therefore, we observe broadened proton peaks. The peaks those appear at 170.63 ppm, 134.59 ppm and 75.57 ppm in 13 C NMR spectrum can not be observed in DEPT 135 spectrum (Figure 2e). Henceforth, it can be concluded that they belong to c spectrum, CH 2 appears in the negative phase.…”

Section: Nmr Studiesmentioning

confidence: 92%

“…Therefore, Figure 2b is obtained in MeOD and C13 has been identified. The peak appearing at 170.00 ppm in 13 C NMR spectrum cannot be observed in DEPT 45 and 135 spectra (Figure 2d). Henceforth, it can be concluded that it is C11.…”

Section: Nmr Studiesmentioning

confidence: 93%

“…For the NMR calculations, molecular structures of optimized at B3LYP/6-31G(d) level in chloroform ( After optimization, 1 H and 13 GIAO method [23][24][25][26][27][28][29][30] in chloroform at the B3LYP/6 Relative chemical shifts were then estimated by using the corresponding TMS shieldings calculated in advance at the same theoretical levels isotropic chemical shieldings for TMS at the B3LYP/6 using the IEFPCM were 31.87 ppm and 183.76 ppm, respectively. Experimental chemical shieldings for TMS are given as pectroscopic and quantum mechanical investigations of two ferrocene derivatives Bull.…”

Section: Calculationsmentioning

confidence: 99%

“…On the other hand, some ligands and complexes including ferrocene moiety were prepared for the inorganic applications [8][9][10][11]. Ferrocenoyl amino acids and peptides were prepared using acyl ferrocenes and investigated in detail [12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

“…In this research two new ferrocene derivatives Fc-3ppa and Fc-3pica were synthesized and characterized by using 1D or 2D NMR experiments such as 1 H, 13 C, DEPT 45-135, HETCOR and COSY techniques. FT-IR spectra were also reported to identify some important vibrational bands of the compounds.…”

Section: Introductionmentioning

confidence: 99%

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FT-IR, NMR spectroscopic and quantum mechanical investigations of two ferrocene derivatives

Alver¹,

Parlak²

2017

Bull. Chem. Soc. Eth.

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ABSTRACT. New ferrocene derivatives as N-(3-piperidin-1-ylpropyl)ferrocenamide and N-(pyridine-3-ylmethyl)ferrocenamide (Fc-3pica) and structural investigations were carried out with 1 H, 13 C, DEPT 45 or 135, HETCOR, COSY NMR and FT-IR spectroscopic techniques. Characterization of Fc-3ppa (FeC19H26N2O) and Fc-3pica (FeC17H16N2O) was also supported by density functional theory (DFT) used by B3LYP functional and 6-31G(d) or 6-311++G(d,p) basis sets. From the combination of all the results, it can be clearly seen that syntheses of Fc-3ppa and Fc-3pica have been successfully achieved. Theoretical values are successfully compared against experimental data and B3LYP method is able to provide satisfactory results for predicting NMR properties and vibrational frequencies of the synthesized ferrocene based systems.

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Section: Nmr Studiesmentioning

confidence: 92%

Section: Nmr Studiesmentioning

confidence: 93%

Section: Calculationsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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FT-IR, NMR spectroscopic and quantum mechanical investigations of two ferrocene derivatives

Alver¹,

Parlak²

2017

Bull. Chem. Soc. Eth.

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Properties of Disubstituted Ferrocene–Peptide Conjugates

2013

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The first oxalamide‐bridged ferrocene: Facile synthesis, preliminary conformational analysis and biological evaluation

Kovač

Radošević²,

Bebek

et al. 2016

Applied Organom Chemis

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tert‐Butyl‐1′‐methoxycarbonyl‐1‐ferrocenecarbamate (1) was Boc‐deprotected to give free amine which underwent oxalyl chloride‐mediated dimerization. The structure of the so‐obtained oxalamide‐bridged ferrocene 2 was elucidated using infrared and NMR (1H, 13C, COSY, NOESY, HSQC, HMBC) spectroscopies, crystal structure analysis, and electrospray ionization and high‐resolution mass spectrometry. The preliminary conformational analysis in solution suggested the intramolecular engagement of oxalamide protons, while single‐crystal analysis revealed an intermolecular hydrogen‐bonding pattern. Also, the effect of oxalamide‐bridged ferrocene 2 on cell viability of three human cell lines (HEK293T, HeLa and HepG2) was tested. In vitro screening revealed proliferative as well as cytotoxic effects of the tested compound in the applied concentration range (1–350 μM) on HEK293T and HepG2 cells. Stimulatory effect on cell growth was the most pronounced for normal HEK293T cells, while the highest cytotoxic effect was observed towards HeLa tumour cells and it was dose‐dependent. The observed dual biological activity of 2 implies its potential application in drug development.

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Changes in the hydrogen bonding pattern in ferrocene peptides

Cited by 48 publications

References 49 publications

FT-IR, NMR spectroscopic and quantum mechanical investigations of two ferrocene derivatives

FT-IR, NMR spectroscopic and quantum mechanical investigations of two ferrocene derivatives

Properties of Disubstituted Ferrocene–Peptide Conjugates

The first oxalamide‐bridged ferrocene: Facile synthesis, preliminary conformational analysis and biological evaluation

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