Novel ferrocene imide derivatives: synthesis, conformational analysis and X-ray structure

Semenčić, Mojca Čakić; Kodrin, Ivan; Molčanov, Krešimir; Kovačević, Monika; Rapić, Vladimir

doi:10.1016/j.heliyon.2022.e09470

Cited by 6 publications

(6 citation statements)

References 40 publications

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“…Furthermore, the geometry around the S(1) atom deviates from the distorted tetrahedral, and the maximum and minimum angles around S(1) are ~106.2° and ~119.5°; this is similar to those reported for other organic sulfonamides[48,49] and organometallic sulfonamides with ferrocenyl group[29,41]. Finally, the substituted and unsubstituted Cp unit contained in the ferrocenyl moiety are nearly eclipsed, like other monosubstituted ferrocenyl derivatives[50].…”

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confidence: 79%

Rational Design and Convenient Synthesis of Two Novel Ferrocene-Based Sulfonyl Diamine Precursors

Gallardo¹,

Arancibia²,

Roussel

et al. 2023

J. Chil. Chem. Soc.

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In the search of new organometallic precursors, this contribution describes a convenient synthesis to obtain new ferrocene-based sulfonyl diamine derivatives. The [(η 5 -C5H4SO2NH-CH2-CH2-NH2)Fe(η 5 -C5H5)] (1) and [(η 5 -C5H4SO2NH-C6H4-NH2)Fe(η 5 -C5H5)] (2) compounds were prepared by the reaction between (η 5 -C5H4SO2Cl)Fe(η 5 -C5H5) and the respective diamine precursor: ethylenediamine (1) or p-phenylenediamine (2) in good yields (86% for 1; 70% for 2). Both compounds were characterized by conventional spectroscopic techniques (infrared spectroscopy, nuclear magnetic resonance spectroscopy, mass spectrometry and elemental analysis) and cyclic voltammetry. In addition, the molecular structure of 1 was determined by single-crystal X-ray diffraction.

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confidence: 79%

Rational Design and Convenient Synthesis of Two Novel Ferrocene-Based Sulfonyl Diamine Precursors

Gallardo¹,

Arancibia²,

Roussel

et al. 2023

J. Chil. Chem. Soc.

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“…Systematic conformational analysis by means of computational chemistry methods can provide us with additional information on the intramolecular hydrogen bonding pattern and folding properties arising from a different side chain of the amino acids used in the synthesis. Over the past decade, we have used a hierarchical approach to study monosubstituted and disubstituted ferrocene-based derivatives [ 19 , 20 , 21 , 22 , 23 , 24 , 49 , 50 , 51 ]. The Monte Carlo Multiple Minimum and Mixed torsional/Low-mode sampling, as implemented in MacroModel [ 52 , 53 ], were used as a starting point for a relatively fast search of conformers with the OPLS2005 force field.…”

Section: Resultsmentioning

confidence: 99%

“…Interestingly, a ferrocene chromophore also shows a potential to be used as a chiroptical probe for determining the helicity not only in disubstituted but in monosubstituted ferrocene derivatives as well. We have described a clear dependence between the sign of the CD spectra (near 470 nm) and torsion angle describing the inclination of the amide bond plane from the plane of the cyclopentadienyl ring [ 20 , 21 , 22 , 23 , 24 ].…”

Section: Introductionmentioning

confidence: 99%

Hydrogen Bonding Drives Helical Chirality via 10-Membered Rings in Dipeptide Conjugates of Ferrocene-1,1′-Diamine

Kovačević

Markulin²,

Zelenika³

et al. 2022

IJMS

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Considering the enormous importance of protein turns as participants in various biological events, such as protein–protein interactions, great efforts have been made to develop their conformationally and proteolytically stable mimetics. Ferrocene-1,1′-diamine was previously shown to nucleate the stable turn structures in peptides prepared by conjugation with Ala (III) and Ala−Pro (VI). Here, we prepared the homochiral conjugates of ferrocene-1,1′-diamine with l-/d-Phe (32/35), l-/d-Val (33/36), and l-/d-Leu (34/37) to investigate (1) whether the organometallic template induces the turn structure upon conjugation with amino acids, and (2) whether the bulky or branched side chains of Phe, Val, and Leu affect hydrogen bonding. Detailed spectroscopic (IR, NMR, CD), X-ray, and DFT studies revealed the presence of two simultaneous 10-membered interstrand hydrogen bonds, i.e., two simultaneous β-turns in goal compounds. A preliminary biological evaluation of d-Leu conjugate 37 showed its modest potential to induce cell cycle arrest in the G0/G1 phase in the HeLa cell line but these results need further investigation.

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“…To better understand the conformational preferences in simple ferrocene peptidomimetics and explain the most common intramolecular hydrogen bonding patterns, we commonly rely on a hierarchical approach to computational modeling [6,31,36,[41][42][43][44][45][46][47][48][49][50][51]. A relatively fast Monte Carlo conformational analysis resulted in the first set of conformers suitable for further optimizations at higher levels of theory in the implicitly modeled solvent.…”

Section: Computational Studymentioning

confidence: 99%

Biological Evaluation and Conformational Preferences of Ferrocene Dipeptides with Hydrophobic Amino Acids

et al. 2023

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Despite the large number of peptidomimetics with incorporated heteroannularly functionalized ferrocenes, few studies have investigated their bioactivity. Here, we report the biological evaluation and conformational analysis of enantiomeric dipeptides derived from 1′-aminoferrocene-1-carboxylic acid (Fca) and hydrophobic amino acids (AA = Val, Leu, Phe). The conformational properties of Y-AA-Fca-OMe (Y = Ac, Boc) were elucidated by experimental (IR, NMR, CD, and X-ray) and theoretical (DFT) methods. The prepared dipeptides were screened for their antimicrobial activity against selected Gram-positive and Gram-negative bacteria, lactic acid bacteria and yeasts, while their antioxidant activity was tested by DPPH and FRAP methods. Of all compounds tested, dipeptide D-2a showed the best antibacterial properties against S. aureus, B. subtilis, and P. aeruginosa at a concentration of 2 mM. The time–kill curves showed that antibacterial activity was concentration- and time-dependent. Chirality (D-) and a more polar-protecting group (Ac) were found to affect the biological activity, both antimicrobial and antioxidant. All investigated peptides are considered to be highly hydrophobic and chemically stable in both acidic and buffer media. Dipeptides D-1a–3a, which showed biological activity, were subjected to the determination of proteolytic activity, revealing very good resistance to proteolysis in the presence of chymotrypsin.

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Novel ferrocene imide derivatives: synthesis, conformational analysis and X-ray structure

Cited by 6 publications

References 40 publications

Rational Design and Convenient Synthesis of Two Novel Ferrocene-Based Sulfonyl Diamine Precursors

Rational Design and Convenient Synthesis of Two Novel Ferrocene-Based Sulfonyl Diamine Precursors

Hydrogen Bonding Drives Helical Chirality via 10-Membered Rings in Dipeptide Conjugates of Ferrocene-1,1′-Diamine

Biological Evaluation and Conformational Preferences of Ferrocene Dipeptides with Hydrophobic Amino Acids

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