Synthesis, Cytotoxicity, and Antileishmanial Activity of N,N'-Disubstituted Ethylenediamine and Imidazolidine Derivatives

Carvalho, Gustavo Senra Gonçalves de; Machado, Patrícia de Almeida; Paula, Daniela T. S. de; Coimbra, Elaine Soares; Silva, Adilson David da

doi:10.1100/tsw.2010.176

Cited by 21 publications

(12 citation statements)

References 22 publications

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“…In this regard Amberlyst 15 possesses properties such as non-hazardous, chemical and physical stability and can be recycled and used over a prolonged period. It catalyzes a wide variety of reactions in heterogeneous phase [24][25][26][27][28][29][30][31][32][33][34][35][36], and recently was used for the synthesis of bis (heterocyclyl) methane derivatives from heteroaryl species and carbonyl substrates [37].…”

Section: Resultsmentioning

confidence: 99%

“…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%

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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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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

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

Perillo¹,

Villalonga²,

Amiano³

et al. 2013

OJMC

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“…Concerning the amastigotes in vitro model, inflammatory macrophages were obtained from BALB ⁄ c mice previously inoculated intraperitoneally with 2 mL of 3% thioglycollate medium (Sigma) (22,23). Briefly, peritoneal macrophages were plated at 2 · 10 6 cells ⁄ mL on coverslips (13 mm diameter) previously arranged in a 24-well plate in RPMI 1640 medium supplemented with 10% inactivated FBS and allowed to adhere for 24 h at 37°C in 5% CO 2 .…”

Section: Pharmacologymentioning

confidence: 99%

Effect of 3‐Alkylpyridine Marine Alkaloid Analogues in Leishmania Species Related to American Cutaneous Leishmaniasis

et al. 2012

Self Cite

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These authors contributed equally in this work.A series of oxygenated analogues of marine 3-alkylpyridine alkaloids were synthesized, and their leishmanicidal activity was assayed. All compounds were prepared from 3-pyridinepropanol in few steps and in good yields. The key step for the synthesis of these compounds was a classic Williamson etherification under phase-transfer conditions. Besides toxicity in peritoneal macrophages, the compounds exhibited a significant leishmanicidal activity. Of twelve compounds tested, five showed a strong leishmanicidal activity against promastigote forms of Leishmania amazonensis and L. braziliensis with IC 50 below 10 lM. Compounds 11, 14, 15, and 16 showed a strong leishmanicidal activity on intracellular amastigotes (IC 50 values of 2.78; 0.27; 1.03, and 1.33 lM, respectively), which is unlikely to be owing to the activation of nitric oxide production by macrophages.

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“…In a recent work our research group performed biological evaluation of hexahydropyrimidines compounds, which form an interesting type of aliphatic azaheterocycle [ 1 , 2 ]. Heterocyclic compounds are of great importance in medicinal chemistry, as they are used as potential targets against several bacterial and parasitic pathogens [ 3 , 4 ].…”

Section: Introductionmentioning

confidence: 99%

In VitroAntifungal Activity of Hexahydropyrimidine Derivatives against the Causative Agents of Dermatomycosis

Martins

Caneschi

Senra

et al. 2017

The Scientific World Journal

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Nitrogenated heterocyclic compounds are present in both natural and synthetic drugs, and hexahydropyrimidine derivatives may prove to be efficient in treating dermatomycosis causing fungi. This study evaluated the antifungal activity of four hexahydropyrimidine derivatives against the dermatomycosis causing fungi. These derivatives were synthesized, characterized, and assessed in terms of their activity against Trichophyton mentagrophytes, Microsporum canis, Microsporum gypseum, Trichophyton rubrum, Fusarium oxysporum, and Epidermophyton floccosum between concentrations 7.8 and 1,000 μg mL−1. Scanning electron micrographs were assessed for the active derivatives and reference drugs, and these micrographs revealed that new agents cause morphological changes in fungi. The derivatives HHP1, HHP3, and HHP4 revealed poor activity against the four fungal strains (MICs range 500–1000 μg mL−1). Compound HHP3 was found to be the best potential antifungal agent among those tested and was the most effective among all the active derivatives that caused morphological changes in the susceptible strains.

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Synthesis, Cytotoxicity, and Antileishmanial Activity of N,N'-Disubstituted Ethylenediamine and Imidazolidine Derivatives

Cited by 21 publications

References 22 publications

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

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

Effect of 3‐Alkylpyridine Marine Alkaloid Analogues in Leishmania Species Related to American Cutaneous Leishmaniasis

In VitroAntifungal Activity of Hexahydropyrimidine Derivatives against the Causative Agents of Dermatomycosis

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