Synthesis, spectroscopic and biological properties of bis(3-arylimidazolidinyl-1)methanes. A novel family of antimicrobial agents

Perillo, Isabel A.; Repetto, Evangelina; Massa, Rosana; Gutkind, Gabriel; Salerno, Alejandra

doi:10.1016/j.ejmech.2005.03.010

Cited by 9 publications

(6 citation statements)

References 12 publications

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“…Compounds 1 -6 were describedpreviously [18]: the new yields and spectroscopic data obtained confirming their identity shown below. …”

Section: General Datamentioning

confidence: 82%

“…In our original procedure compounds 1 -6 were synthesized in homogenous phase by condensation of N-arylethylenediamines with an excess aqueous formaldehyde (37%) in ethanol under reflux [18]. Precursor N-arylethylenediamines were prepared by aminolysis of 2-bromoethylamine (hydrobromide) with the corresponding arylamine [33].…”

Section: Resultsmentioning

confidence: 99%

“…Among them, we can mention bis-imidazolidine-2,4-dione derivatives [13,14] (X = NAr, Y = COCH 2 , Z = CO), bis-oxazolidines [15] (X = O, Y = CH 2 CHCH 3 , Z = CH 2 ), and taurolidine [16,17] (a bisthiadiazine derivative) (X = NH, Y = SO 2 CH 2 CH 2 , Z = CH 2 ). In previous studies we reported the synthesis and antimicrobial activity of a series of novel bis (3-arylimidazolidinyl-1) methanes 1 -6 [18], corresponding to struc-ture A (X = NAr, Y = CH 2 CH 2 , Z = CH 2 ) with two imidazolidine cores. Imidazolidines (tetrahidroimidazoles) are cyclic aminals of pharmacological interest.…”

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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“…Compounds 1 -6 were describedpreviously [18]: the new yields and spectroscopic data obtained confirming their identity shown below. …”

Section: General Datamentioning

confidence: 82%

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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“…On the one hand, imidazolidines are of commercial interest due to their multiple biological activities related to ring substitution [1,2]. Bis(imidazolidinyl)methanes are derived from these heterocycles and have shown excellent antimicrobial, antiparasitic, and antitumor activity [3]. These properties could be related to its hydrophobic nature, which increases the bioavailability of its biologically active precursors (carbonyl and ethylenediamine) [4].…”

Section: Introductionmentioning

confidence: 99%

Structural and Dynamic Behaviour of Heterocycles Derived from Ethylenediamines with Formaldehyde: 1,3,5-Triazinanes and Bis(imidazolidinyl)methanes

2023

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Formaldehyde is a simple chemical compound that is used as a building block in obtaining a wide range of products. The versatility of formaldehyde in chemical synthesis becomes evident when it is reacted with N-alkylethylenediamines. Therefore, this paper reports the structure and reactivity of a series of compounds derived from easily accessible molecules, such as formaldehyde, sodium hydrosulphide, and N-alkylethylenediamines. The 1,3,5-triazines (1a-1d) and bis(3-alkyl-imidazolidin-1-yl)methanes (2a-2d) were obtained by simple reaction conditions. Additionally, different proportions of sodium hydrosulphide and formaldehyde were used with N-benzylamine to obtain N-benzyltriazinane (3), N-benzylthiadiazinane (4) and N-benzyldithiazinane (5). All these compounds were characterized by analytical, spectroscopic, and spectrometric techniques, such as melting point, solubility, one-dimensional and two-dimensional nuclear magnetic resonance (13C, 1H, 15N, COSY, HETCOR, NOESY, COLOC), elemental analysis, high- and low-resolution mass spectrometry, among others. The structures of compounds 4 and 5 were obtained by single-crystal X-ray diffraction. The results show that small variations in the stoichiometry and the reaction conditions significantly influence the products obtained.

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“…Imidazole analogs deal with a variety of bioactivities viz. antitumor [2,3], anti-HIV [4], antimicrobial [5][6][7][8], anticonvulsant [9], antitubercular [10], antiprotozoal [11], anti-inflammatory [12], FTase and MAP kinase p38 inhibitory activities [13,14].…”

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confidence: 99%

Synthesis, Spectral and Antimicrobial Studies on some Newer Imidazole Analogs

Dahiya

2008

Sci Pharm

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A novel series of 3,5-diiodo-4-(2-methyl-1H-imidazol-5-yl)benzoic acid analogs of amino acids, dipeptides and tripeptides was synthesized by using dicyclohexylcarbodiimide and diisopropylcarbodiimide (DCC/DIPC) as coupling agents and triethylamine (TEA) as base. Structures of all the newly synthesized compounds were confirmed by elemental analysis and IR, 1 H NMR, 13 C NMR and mass spectral data. Imidazolopeptides were investigated for their antimicrobial activity and some of newly synthesized compounds 2c, 2d, 2h and their hydrolyzed analogs 3b, 3d exhibited potent bioactivity against pathogenic fungi Candida albicans and dermatophytes Trichophyton mentagrophytes and Microsporum audouinii with MIC values of 12.5-6 μg/ml, as compared to the reference druggriseofulvin. In addition, moderate activity against gram negative bacteria Pseudomonas aeruginosa and Klebsiella pneumoniae was also observed for synthesized imidazolopeptides.

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Synthesis, spectroscopic and biological properties of bis(3-arylimidazolidinyl-1)methanes. A novel family of antimicrobial agents

Cited by 9 publications

References 12 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

Structural and Dynamic Behaviour of Heterocycles Derived from Ethylenediamines with Formaldehyde: 1,3,5-Triazinanes and Bis(imidazolidinyl)methanes

Synthesis, Spectral and Antimicrobial Studies on some Newer Imidazole Analogs

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