Cyrhetrenyl and ferrocenyl 1,3,4-thiadiazole derivatives: Synthesis, characterization, crystal structures and in vitro antitubercular activity

Quintana, Cristóbal; Klahn, A. Hugo; Artigas, Vania; Fuentealba, Mauricio; Biot, Christophe; Halloum, Iman; Kremer, Laurent; Arancibia, Rodrigo

doi:10.1016/j.inoche.2015.03.008

Cited by 27 publications

(14 citation statements)

References 30 publications

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“…In fact, the downfield shift observed for the cyrhetrenyl ( 1a – c ) and cymantrenyl ( 2a – c ) derivatives (Δδ∼0.5) compared with ferrocenyl analogues ( 3a – c ) can be related to the electron-withdrawing properties of the (η 5 -C 5 H 4 )M(CO) 3 moieties 33 , 34 , which produce a deshielding of the NH resonance, thus suggesting that the nature of the organometallic framework modifies the degree of electronic delocalization on the –C(H)=N–NH– unit. We have found similar results for ferrocenyl and cyrhetrenyl hydrazones 19 , 35 and 1,3,4-thiadiazoles 36 . In the case of the acylhydrazones 1c , 2c and 3c , additional signals were observed at 6.44 ppm, 3.36 ppm and 2.80–2.42 ppm, respectively.…”

Section: Resultssupporting

confidence: 81%

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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Section: Resultssupporting

confidence: 81%

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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“…On the other hand, the most interesting feature of the 13 C NMR spectra of the complexes ( 2a–c ) is the presence of a low‐field resonance (159.7–149.2 ppm) assigned to the iminyl carbon (Figures S10–S12). This resonance occurs at almost the same δ as those reported for Ni (II), Pd (II) and Pt (II) complexes containing other organic [ 62,63 ] and organometallic Schiff bases [ 64,65 ] and was corroborated by 1 H– 13 C NMR HSQC (Figure S13). For the three complexes, the resonances of the ferrocenyl moiety showed 13 C shifts similar to those reported for the formylferrocene thiosemicarbazone free ligand.…”

Section: Resultssupporting

confidence: 79%

Synthesis, characterization, X‐ray structure, electrochemistry, photocatalytic activity and DFT studies of heterotrinuclear Ni(II), Pd(II) and Zn(II) complexes containing a formylferrocene thiosemicarbazone ligand

Chung

Huentupil

Rabanal

et al. 2020

Applied Organom Chemis

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Three complexes of the general formula M{CpFe(η5‐C5H4CH=N–N=C(S)NH2}2 [where M = NiII (2a), PdII (2b) and ZnII (2c)] were synthesized with formylferrocene thiosemicarbazone (1) as a bidentate ligand. All compounds were characterized using conventional spectroscopic and analytical techniques (infrared, 1H and 13C NMR, mass spectrometry and elemental analysis). The molecular structure of 2b was confirmed by single‐crystal X‐ray analysis. To study the photocatalytic activity of the new complexes (2a–c), methylene blue (MB) was selected as a model pollutant. After 180 min, the degradation efficiency of MB reached 87% for 2a, 76% for 2b and 85% for 2c, and all complexes showed a higher photocatalytic activity than the formylferrocene thiosemicarbazone free ligand 1. Theoretical studies were used to characterize the geometry and electronic structure of the compounds and to provide a rational explanation for the measured photocatalytic activity.

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“…This hypothesis is contrasted when it was compared with trypanocidal activity registered to organic analogue Bzn-3 (IC50 = 91 µM), without any substitution. Similar conclusions were previously reported by our group for thiosemicarbazones, 1,3,4-thiadiazoles, chalcones and imine derivatives of 5nitroheterocycles series containing these organic and organometallic moieties [29,30,[75][76][77]. However, all tested compounds presented IC50 values that were higher than benznidazole drug (IC50 = 44 µM).…”

Section: Biological Assays: Antitrypanosomal Activitysupporting

confidence: 90%

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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Cyrhetrenyl and ferrocenyl 1,3,4-thiadiazole derivatives: Synthesis, characterization, crystal structures and in vitro antitubercular activity

Cited by 27 publications

References 30 publications

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

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

Synthesis, characterization, X‐ray structure, electrochemistry, photocatalytic activity and DFT studies of heterotrinuclear Ni(II), Pd(II) and Zn(II) complexes containing a formylferrocene thiosemicarbazone ligand

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

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