Imidazolidines as new anti-Trypanosoma cruzi agents: Biological evaluation and structure–activity relationships

Caterina, María Cristina; Perillo, Isabel A.; Boiani, Lucı́a; Pezaroglo, Horacio; Cerecetto, Hugo; González, Mercedes; Salerno, Alejandra

doi:10.1016/j.bmc.2007.11.077

Cited by 69 publications

(56 citation statements)

References 47 publications

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“…cruzi Tulahuen 2 strain epimastigotes were grown at 28 °C in an axenic medium (BHItryptose) as previously described, [19][20][21][54][55][56][57] complemented with 5% fetal bovine serum.…”

Section: In Vitro Anti-t Cruzi Tulahuen 2 Strain Assaymentioning

confidence: 99%

Novel quinoxaline 1,4-di-N-oxide derivatives as new potential antichagasic agents

Torres

Moreno‐Viguri

Galiano

et al. 2013

European Journal of Medicinal Chemistry

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ABSTRACT. As a continuation of our research and with the aim of obtaining new agents against Chagas disease, an extremely neglected disease which threatens 100 million people, eighteen new quinoxaline 1,4-di-N-oxide derivatives have been synthesized following the Beirut reaction. The synthesis of the new derivatives was optimized through the use of a new and more efficient microwave-assisted organic synthetic method. The new derivatives showed excellent in vitro biological activity against Trypanosoma cruzi. Compound 17, which was substituted with 2 fluoro groups at the 6-and 7-positions of the quinoxaline ring, was the most active and selective in the cytotoxicity assay. The electrochemical study showed that the most active compounds, which were substituted by electron-withdrawing groups, possessed a greater ease of reduction of the N-oxide groups.

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“…cruzi Tulahuen 2 strain epimastigotes were grown at 28 °C in an axenic medium (BHItryptose) as previously described, [19][20][21][54][55][56][57] complemented with 5% fetal bovine serum.…”

Section: In Vitro Anti-t Cruzi Tulahuen 2 Strain Assaymentioning

confidence: 99%

Novel quinoxaline 1,4-di-N-oxide derivatives as new potential antichagasic agents

Torres

Moreno‐Viguri

Galiano

et al. 2013

European Journal of Medicinal Chemistry

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“…These compounds were evaluated against 60 human cell lines derived from seven clinically isolated cancer types (lung, colon, melanoma, renal, ovarian, brain and leukemia) according to a standard protocol (conducted at the National Cancer Institute, Bethesda, MD, USA) with the sulforhodamine B (SRB) assay [21][22][23][24]. The evaluated compounds 1 y 2 showed antitumor activity for the leukemia cells lines CCRF-CEM, K-562, MOLT-4 and RPMI 8226; for non-small cell lung cancer HOP-92, NCI-H23; colon cancer HCC-2998, HCT-15, SW-620; melanoma LOX IMVI cell line, IGROV1 ovarian cancer and renal cancer A486 and ACHN.…”

Section: Resultsmentioning

confidence: 99%

“…Imidazolidines (tetrahidroimidazoles) are cyclic aminals of pharmacological interest. They have shown fungicide, bactericide, antiviral, [19][20][21] antiTrypanosoma cruzi [22,23] and antileshmanial activity [24]. Other properties such as anti-inflammatory [19], analgesic [19], estrogenic [25] and tumor inhibition [26,27] activities have been also reported.…”

Section: Introductionmentioning

confidence: 99%

New Green Synthesis and Antineoplastic Activity of Bis (3-Arylimidazolidinyl-1) Methanes

Perillo¹,

Villalonga²,

Amiano³

et al. 2013

OJMC

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A new green synthesis and anti-tumor activity of the series of bis (3-arylimidazolidinyl-1) methanes 1 -6 are described. The compounds were synthesized from the corresponding N-arylethylenediamine and trioxane as sources of formaldehyde and the reactions were performed in heterogeneous phase catalyzed by an acidic ion-exchange resin (Amberlyst 15). The compounds were tested with the Sulforhodamine B assay according to the protocol of the National Cancer Institute for several cell lines. The results were expressed as percentage inhibition of growth cell in comparison with the full growth of the cells without treatment. Cytotoxicity on normal cells using the Annexing-PI staining and flow cytometry has been evaluated. The parent compound, bis(3-phenylimidazolidinyl-1)methane 1 and the monohalogenated derivatives 4-chlorophenyl 3 and 3-bromophenyl 5 showed antineoplastic activity, 60%, 82% and 89% inhibition growth cell respectively on the human colon cell line (HCT116). The 4-tolyl derivative 6 presented inhibitory activity (73% inhibition of growth cell) on human lung adenocarcinoma cell line (A549) and 62% on human mammary cell line MCF-7.

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“…Compound R NMR spectroscopic methods have been successfully used for obtaining information about the stereochemistry of amides. 5,6 In line with our previous studies related to spectral and biological properties of imidazolidines, [1][2][3][4] we prepared a series of 1-acyl-3-arylimidazolidines 11 (heterocyclic tertiary amides). Because the complete knowledge of structure, including stereochemistry, is essential for lead optimization in drugs discovery, we report herein our studies concerning the structural features of several of those compounds (1-15) ( Table 1) as studied by NMR spectroscopy.…”

Section: Introductionmentioning

confidence: 84%

“…Some of these compounds have biological activity, which is strongly dependent on their substitution patterns. 1 In order to elucidate structure-activity correlations, the study of their conformational features, specially the substituent orientation in molecules of biological interest, has been the object of several investigations. Our laboratory has used 1 H-and 13 C-NMR spectroscopy to study the conformational characteristics of imidazolidines having different substitution patterns (alkyl or aryl groups) at 2,3 Electron delocalization originating from the contribution of structure II (Figure 1) gives partial double-bond character to the N-CO amide bond in its ground state, with rotational barriers in the 15-23 kcal/mol range, [5][6][7][8][9] causing the geometric and magnetic non-equivalence of the nitrogen substituents when R .…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic analysis of imidazolidines Part V: 1H and 13C NMR spectroscopy and conformational analysis of N-acylimidazolidines

Corona¹,

Santos²,

Abasolo³

et al. 2014

Arkivoc

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The conformational features of a series of 1-acyl-3-arylimidazolidines 1-14 were correlated with their 1 H and 13 C-NMR spectra. Due to the hindered rotation around the N-CO bond, these compounds exist in solution as a mixture of non-isolable Z/E diastereomers, the Z-isomer being the most abundant in all cases. The analysis of NOESY spectra confirmed the complete assignment of the 1 H-NMR resonances of each rotamer. Two-dimensional heteronuclear HMQC and HMBC spectra of selected compounds permitted the assignment of 13 C-NMR signals. We analyzed the influence of the imidazolidine ring substituents on the equilibrium abundance of Z/E isomers. We also studied the spectroscopic and conformational properties of a 1-acyl-2,3-diarylimidazolidine 15, which revealed the effect of the C-2 substitution.

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Imidazolidines as new anti-Trypanosoma cruzi agents: Biological evaluation and structure–activity relationships

Cited by 69 publications

References 47 publications

Novel quinoxaline 1,4-di-N-oxide derivatives as new potential antichagasic agents

Novel quinoxaline 1,4-di-N-oxide derivatives as new potential antichagasic agents

New Green Synthesis and Antineoplastic Activity of Bis (3-Arylimidazolidinyl-1) Methanes

Spectroscopic analysis of imidazolidines Part V: 1H and 13C NMR spectroscopy and conformational analysis of N-acylimidazolidines

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