Cyrhetrenylaniline and new organometallic phenylimines derived from 4- and 5-nitrothiophene: Synthesis, characterization, X-Ray structures, electrochemistry and in vitro anti- T. brucei activity

Toro, Patricia M.; Suazo, Constanza; Acuña, Alejandra; Fuentealba, Mauricio; Artigas, Vania; Arancibia, Rodrigo; Olea‐Azar, Claudio; Moncada‐Basualto, Mauricio; Wilkinson, Shane R.; Klahn, A. Hugo

doi:10.1016/j.jorganchem.2018.03.004

Cited by 17 publications

(8 citation statements)

References 71 publications

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“…Bond distances and angles are in the expected ranges and agree well with values observed for similar compounds (see e.g. Kumar et al, 2020;Shabbir et al, 2017;Toro et al, 2018). The unsubstituted cyclopentadienyl ring, C1-C5, was found to be rotationally disordered, with a refined occupancy of 0.666 (7) for the major moiety.…”

Section: Structural Commentarysupporting

confidence: 86%

Crystal structure and Hirshfeld surface analysis study of (E)-1-(4-chlorophenyl)-N-(4-ferrocenylphenyl)methanimine

Sghyar¹,

Moussaoui²,

Sebbar³

et al. 2021

Acta Crystallogr E Cryst Commun

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The substituted cyclopentadienyl ring in the title molecule, [Fe(C5H5)(C18H13ClN)], is nearly coplanar with the phenyl-1-(4-chlorophenyl)methanimine substituent, with dihedral angles between the planes of the phenylene ring and the Cp and 4-(chlorophenyl)methanimine units of 7.87 (19) and 9.23 (10)°, respectively. The unsubstituted cyclopentadienyl ring is rotationally disordered, the occupancy ratio for the two orientations refined to a 0.666 (7)/0.334 (7) ratio. In the crystal, the molecules pack in `bilayers' parallel to the ab plane with the ferrocenyl groups on the outer faces and the substituents directed towards the regions between them. The ferrocenyl groups are linked by C—H...π(ring) interactions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (46.1%), H...C/C... H (35.4%) and H...Cl/Cl...H (13.8%) interactions. Thus C—H...π(ring) and van der Waals interactions are the dominant interactions in the crystal packing.

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Section: Structural Commentarysupporting

confidence: 86%

Crystal structure and Hirshfeld surface analysis study of (E)-1-(4-chlorophenyl)-N-(4-ferrocenylphenyl)methanimine

Sghyar¹,

Moussaoui²,

Sebbar³

et al. 2021

Acta Crystallogr E Cryst Commun

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“…First, there was a linear correlation between the nitro-reduction (E½) with the anti-T. cruzi activity (IC50). Similar results have been previously reported for related 5nitrofurane compounds with anti-chagasic activity [29,30,34]. Second, the cyrhetrenyl derivative (Bzn-1) (IC50 = 80 µM) is a more potent trypanocidal agent than its ferrocenyl analogue (Bzn-2) (IC50 > 100 µM).…”

Section: Biological Assays: Antitrypanosomal Activitysupporting

confidence: 86%

“…As part of our continued interest in the study on the electronic influence of the organometallic entities on bioconjugates with potential antiparasitic activity [29,30,34], we decided to study 5-nitro-benzimidazoles containing ferrocenyl (electron-donating) and cyrhetrenyl (electron-withdrawing) moieties into their structure. To do this we inspired in few reports dealing with ferrocenylbenzimidazoles as fungicidal [47,48], antitumoral [49,50] and antimalarial agents [35].…”

Section: Resultsmentioning

confidence: 99%

“…In the last years, we reported the synthesis and anti-trypanosomal evaluation of the first organometallic-organic hybrids containing 5-nitrofurane and 5nitrothiophene groups [29][30][31][32][33][34]. Biological studies against T. cruzi (epimastigotes and trypomastigotes) showed a potent trypanocidal activity of the cyrhetrenyl imines derivatives from 5-nitrofuranyl and 5-nitrothiophenyl fragments, compared with ferrocenyl or purely organic analogues.…”

Section: Introductionmentioning

confidence: 99%

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ELECTROCHEMICAL, ESR, THEORETICAL STUDIES AND in vitro ANTI-T. cruzi ACTIVITY OF 2-ORGANOMETALLIC-5-NITRO-BENZIMIDAZOLES

Barriga-González¹,

Olivares-Petit²,

Toro³

et al. 2020

J. Chil. Chem. Soc.

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The bioorganometallic compounds 2-cyrhetrenyl-5-nitro-benzimidazole (Bzn-1) and 2-ferrocenyl-5-nitro-benzimidazole (Bzn-2) have been proposed as potential anti-Trypanosoma cruzi agents. In this regard, electrochemical, electron spin resonance and biological studies were carried out. Cyclic voltammetry experiments showed the generation of nitro anion radical derivatives and a self-protonation process was observed. Nitro anion radicals generated were characterized and analyzed using electron spin resonance spectroscopy. The compounds were tested in vitro against Trypanosoma cruzi (Dm28c strain). Biological evaluation display that 2cyrhetrenyl-5-nitro-benzimidazole (Bzn-1) was more active than its ferrocene analogue (Bzn-2) and purely organic derivate (Bzn-3), associated with the electronwithdrawing properties of the (η 5-C5H4)Re(CO)3 moiety. Finally, theoretical studies were carried out in order to elucidate the correlation between organometallic fragment, nitro-reduction potentials and trypanocidal activity.

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“…In addition, the spectra for 1c , 2c, and 3c exhibited an absorption band for νC sp3 –H at ∼2950 cm −1 . Furthermore, the IR spectra of cyrhetrenyl ( 1a – c ) and cymantrenyl ( 2a – c ) acylhydrazones revealed the presence of terminal metal carbonyl groups in the region of 2027–1912 cm −1 23–25 . A strong molecular ion was shown in the mass spectrum of each organometallic-acylhydrazones, in addition to the detection of notable successive losses of CO ligands for the cyrhetrenyl ( 1a – c ) and cymantrenyl ( 2a – c ) derivatives.…”

Section: Resultsmentioning

confidence: 94%

New sulfonamides containing organometallic-acylhydrazones: synthesis, characterisation and biological evaluation as inhibitors of human carbonic anhydrases

Huentupil

Peña

Novoa

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of organometallic acylhydrazones was prepared, incorporating Re(CO)3, Mn(CO)3 and ferrocenyl moieties, which were subsequently reacted with amino-sulfonamides in order to obtain carbonic anhydrase (CA, EC 4.2.1.1) inhibitors possessing organometallic moieties in their molecules. The new derivatives were investigated as inhibitors of four human (h) CA isoforms with pharmaceutical applications, such as the cytosolic hCA I, II and VII and the mitochondrial hCA VA. An interesting inhibitory profile against these isoforms was obtained, with some of these metal complexes acting as subnanomolar or low nanomolar inhibitors. They were also thoroughly characterised from the chemical point of view, making them of interest for further developments in the field of metal complexes of sulfonamides with CA inhibitory action.

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Cyrhetrenylaniline and new organometallic phenylimines derived from 4- and 5-nitrothiophene: Synthesis, characterization, X-Ray structures, electrochemistry and in vitro anti- T. brucei activity

Cited by 17 publications

References 71 publications

Crystal structure and Hirshfeld surface analysis study of (E)-1-(4-chlorophenyl)-N-(4-ferrocenylphenyl)methanimine

Crystal structure and Hirshfeld surface analysis study of (E)-1-(4-chlorophenyl)-N-(4-ferrocenylphenyl)methanimine

ELECTROCHEMICAL, ESR, THEORETICAL STUDIES AND in vitro ANTI-T. cruzi ACTIVITY OF 2-ORGANOMETALLIC-5-NITRO-BENZIMIDAZOLES

New sulfonamides containing organometallic-acylhydrazones: synthesis, characterisation and biological evaluation as inhibitors of human carbonic anhydrases

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