Nitro-imidazoles in ferrocenyl alkylation reaction. Synthesis, enantiomeric resolution and in vitro and in vivo bioeffects

Snegur, L. V.; Lyapunova, Maria V.; Verina, Daria D.; Качала, В. В.; Korlyukov, Alexander A.; Ilyin, M. M.; Davankov, V. A.; Ostrovskaya, L. A.; Bluchterova, N. V.; Фомина, М. М.; Malkov, Victor S.; Nevskaya, K. V.; Pershina, Alexandra G.; Simenel, А. А.

doi:10.1016/j.jorganchem.2018.06.019

Cited by 13 publications

(26 citation statements)

References 49 publications

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“…Earlier, this method of separation was successfully used for racemic ferrocene compounds with different simple substituents, the chiral sorbents based upon β ‐ and γ ‐cyclodextrins turned out to be effective in these cases. To separate mixtures of racemic ferrocene derivatives having bulky substituents such as azoles including thiazoles and nitro‐imidazoles we used modified cellulose or amylose as chiral stationary phases.…”

Section: Resultsmentioning

confidence: 99%

“…Antitumor activity of ferrocene compounds is presently under active investigations, and the authors have also succeeded in this field . However, at the moment there are only a few publications on the effects of the ferrocene‐substituted compounds on the brain .…”

Section: Resultsmentioning

confidence: 99%

“…Antitumor activity of ferrocene compounds is presently under active investigations, [15][16][17][18] and the authors have also succeeded in this field. [28,29,54,55] However, at the moment there are only a few publications on the effects of the ferrocene-substituted compounds on the brain. [21][22][23][24][25]56,57] This subject is only beginning to attract the attention of scientists working in the field of organometallic chemistry.…”

Section: Biological Tests Electrophysiological Measurements In Thementioning

confidence: 99%

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Administration of ferrocene‐modified amino acids induces changes in synaptic transmission in the CA1 area of the hippocampus

Rodionov

Snegur

Dobryakova

et al. 2019

Applied Organom Chemis

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A series of ferrocene‐modified amino acid methyl esters with pyrazole linker was prepared in good to quantitative yields starting from easy accessible ferrocene pyrazole carbaldehyde and amino acids in racemic and enantio enriched forms under reductive amination conditions (NaBH (OAc)3, reflux, 3 hr). The resulting enantiomers were resolved using analytical HPLC on modified cellulose or amylose as chiral selectors. In vivo electrophysiological experiments were performed in the CA1 field of the hippocampus on 3a Fc‐Gly, (L)‐3b Fc‐Ala, and (D)‐3b Fc‐Ala compounds. An increasing in the amplitudes of responses of local potentials (up to 25%) of the CA1 region in the studied groups was found after intraperitoneal administration of ferrocene compounds 3a and (D)‐3b compared with control rats treated with saline.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Biological Tests Electrophysiological Measurements In Thementioning

confidence: 99%

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Administration of ferrocene‐modified amino acids induces changes in synaptic transmission in the CA1 area of the hippocampus

Rodionov

Snegur

Dobryakova

et al. 2019

Applied Organom Chemis

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“…Synthesis of ferrocene‐modified N ‐heterocycles; where the heterocycles are: imidazole ( 1 ), pyrazole ( 2 ), 3, 5‐dimethylpyrazole ( 3 ), 2‐methyl‐4‐nitroimidazole, R = Me ( 4 ), R = Ph ( 5 ); benzotriazole ( 6 ); conditions: (i) CDI, CH 2 Cl 2 , Δ, 1h [41]; (ii) HBF 4 /H 2 O‐CH 2 Cl 2 , room temperature, 5 min [26,36,42]. Stereogenic carbon atoms are indicated by an asterisk.…”

Section: Introductionmentioning

confidence: 99%

Application of capillary electrophoresis technique for the enantioseparation of bioactive ferrocene‐based compounds versus DFT calculated data

et al. 2020

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Herein, a series of bioactive ferrocene‐modified N‐heterocycles with alkyl linkers was prepared in good to quantitative yields starting from easy accessible ferrocene alcohols and heterocycles under acidic or neutral (for imidazole) conditions in racemic forms. The analytical resolution of a number of bioactive racemic ferrocene azoles 1–6 (where azole = imidazole, pyrazole, and benzotriazole derivatives) into enantiomers was first carried out by CE using sulfobuthylether‐β‐CD (captisol) as a chiral selector. The analytical approaches to highly enantiomeric‐enriched ferrocene derivatives are based on the formation of their inclusion complexes. The best chiral separation was achieved using zone CE in a quartz capillary. The ACE was used to evaluate the stability constants of captisol complexes with enantiomeric forms of two ferrocene derivatives 1, FcCHMe‐imidazole, and 6, FcCHMe‐benzotriazole. The optimal conditions for the resolution of the studied (R, S)‐ferrocene compounds 1, 2, and 6 were predicted on the basis of the performed quantum chemical calculations and then implemented by the electrophoretic method. A high correlation between density functional theory calculation results and experimental electrophoresis data were obtained. Successful enantioseparation of racemic mixtures is of great importance for the characterization and further applications of drug candidates in enantiopure forms and in the development of clinical treatment. The advantages of the CE procedure make it possible to have important practical value and significance for determining the purity and enantiomeric excess of other ferrocene‐containing compounds.

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“…However, these drugs produce significant side effects such as peripheral neuropathy, anorexia, vomiting and allergies, as well as considerable cardiac and renal toxicity [8][9][10]. While the toxic effects and the mechanisms of action of NFX and BNZ are not yet fully understood [11][12][13], many new antitrypanosomal agents have been developed with derivatives structurally related to these drugs [14][15][16][17][18][19][20]. That is, several studies propose that the bioreduction of the nitro group causes a trypanocidal effect, generating a serie of reduced metabolites of high toxicity (superoxide anion, hydrogen peroxide and hydroxyl radical) that triggers the oxidative stress into the parasite [21].…”

Section: Introductionmentioning

confidence: 99%

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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Nitro-imidazoles in ferrocenyl alkylation reaction. Synthesis, enantiomeric resolution and in vitro and in vivo bioeffects

Cited by 13 publications

References 49 publications

Administration of ferrocene‐modified amino acids induces changes in synaptic transmission in the CA1 area of the hippocampus

Administration of ferrocene‐modified amino acids induces changes in synaptic transmission in the CA1 area of the hippocampus

Application of capillary electrophoresis technique for the enantioseparation of bioactive ferrocene‐based compounds versus DFT calculated data

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

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