Article  Synthesis and Trypanocidal Activity of Novel  2,4,5-Triaryl-N-Hydroxylimidazole Derivatives

Silva, Ramon Borges da; Loback, Vanessa Brandão; Salomão, Kelly; Castro, Solange L. de; Wardell, Jámes L.; Wardell, Solange M. S. V.; Costa, Thadeu Estevam Moreira Maramaldo; Penido, Carmen; Henriques, Maria das Graças; Carvalho, Samir A.; Silva, Edson Ferreira da; Fraga, Carlos A.M.

doi:10.3390/molecules18033445

Cited by 26 publications

(17 citation statements)

References 22 publications

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“…For example, it has been shown that 1-hydroxyimidazole derivatives display insecticidal and herbicidal properties, 2 exhibit antiprotozoal activity. 3,4 It is supposed that 1-hydroxyimidazoles exist in either Nhydroxy or N-oxide tautomeric form. Scheme 1.…”

Section: Graphical Abstractmentioning

confidence: 99%

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Synthesis and study of prototropic tautomerism of 2-(2-hydroxyphenyl)-1-hydroxyimidazoles

et al. 2015

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Please cite this article as: Nikitina PA, Peregudov AS, Koldaeva TY, Kuz'mina LG, Adiulin EI, Tkach II, Perevalov VP, Synthesis and study of prototropic tautomerism of 2-(2-hydroxyphenyl)-1-hydroxyimidazoles, Tetrahedron (2015), Novel 2-(2-hydroxyphenyl) substituted imidazoles have been synthesized. A prototropic tautomerism of the 1-hydroxyimidazole derivatives has been studied. X-ray diffraction analysis and IR-spectroscopy have revealed that in the solid state the title compounds exist as the Nhydroxy tautomers. The 1 H and 13 C NMR spectra of the new imidazole derivatives are discussed. It has been shown that in chloroform solutions 5-carbonylsubstituted 2-(2-hydroxyphenyl)-1-hydroxyimidazoles exist in the N-hydroxy tautomeric form. A transition to DMSO results in the existence of the 1-hydroxyimidazoles under study as the N-oxide tautomers.

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Section: Graphical Abstractmentioning

confidence: 99%

“…One of the most widespread and convenient methods to synthesize 1-hydroxyimidazoles is a cyclization of starting aldehydes with α-hydroxyiminoketones and ammonium acetate 1,2,4,7,23,24,[26][27][28][29][30] in alcohols or glacial acetic acid. Scheme 2.…”

Section: Synthesis Of Compoundsmentioning

confidence: 99%

Synthesis and study of prototropic tautomerism of 2-(2-hydroxyphenyl)-1-hydroxyimidazoles

et al. 2015

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“…Structures of thiochroman-4-ones ( [1][2][3][4][5] and hydrazone derivatives (6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22). …”

Section: Methodsmentioning

confidence: 99%

“…In addition, numerous hydrazones have been reported to possess interesting biological activities such as antitumoral, antiviral and antiparasitic effects [8][9][10]; some hydrazones also exhibit activity against the parasites that cause malaria, leishmaniasis and Chagas disease [3,[11][12][13][14][15][16][17][18], where the inhibition of proteases and represent the most common mechanism of action for the hydrazones [16,[19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Hydrazone Derivatives Enhance Antileishmanial Activity of Thiochroman-4-ones

Vargas

Echeverri

Upegui

et al. 2018

Preprint

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Cutaneous leishmaniasis (CL) is a neglected tropical disease, which causes severe skin lesions. Due to the lack of effective vaccines, and toxicity or reduced effectiveness of available drugs in addition to complex and prolonged treatments, there is an urgent need to develop alternatives for the treatment for CL with different mechanisms of action. In our effort to search for new promising hits against Leishmania parasites we prepared 18 acyl hydrazone derivatives of thiochroman-4-ones. Compounds were evaluated for their in vitro antileishmanial activity against the intracellular amastigote form of Leishmania panamensis and cytotoxic activity against human monocytes (U-937 ATCC CRL-1593.2). Our results show that derivatization of the thiochroman-4-ones with acyl hydrazones significantly enhances the antileishmanial activity. Among the compounds tested semicarbazone and thiosemicarbazone derivatives of thioflavanone 19 and 20 displayed the highest antileishmanial activities, with EC 50 values of 5.4 and 5.1 µM and low cytotoxicities (100.2 and 50.1 µM respectively), resulting in higher indexes of selectivity (IS).

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“…These 1-hydroxyimidazoles/imidazole N-oxides are among a number of active drugs known to exist in tautomeric forms, at least in solution [7]. Among the therapeutic activities of 1-hydroxyimidazole/imidazole N-oxide compounds are herbicidal [8,9], fungicidal and bacteriosidal [10], antihypertensive [11], antiviral [12] and typanocidal activities [13,14].…”

Section: Introductionmentioning

confidence: 99%

Crystal structures of 1-hydroxylimidazole and imidazole 1-oxide derivatives

Silva¹,

Silva²,

Carvalho³

et al. 2014

Zeitschrift Für Kristallographie - Crystalline Materials

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The N-oxide or 1-hydroxy forms of four solid 1-hydroxy-5-(4-methyl-2-nitroimidazol-2-yl)-4-phenyl-2-(Xphenyl)-imidazole derivatives, 6, have been studied by X-ray crystallography. Compounds, (6: X = 4-Br) and (6: X = 2-O 2 N), both recrystallized from EtOH, and (6: X = 4-F), recrystallized from EtOCH 2 CH 2 OH, were isolated in the 1-hydroxyimidazole form. In contrast, (6: X = H), recrystallized from EtOCH-2 CH 2 OH, was obtained in the imidazole N-oxide form. Two independent molecules, Mol A and Mol B, rotamers, are present in the asymmetric unit of the imidazole N-oxide compound, (6: X = H) and are linked into chains of alternating compounds, mainly by N-H···O hydrogen bonds, but also by N-H···N and C-H···O hydrogen bonds and π···π interactions. These chains are linked by other C-H···O and C-H···N hydrogen bonds and π···π interactions into a 3-D arrangement. In the 1-hydroxyimidazole compound, (6: X = 2-O 2 N), classical hydrogen bonds, O1-H1···N3, are the major interactions linking molecules into C(5) chains: weak π···π stacking interactions also link the molecules within the chains. These chains are linked by C-H···O and hydrogen bonds and by N-O···π interactions into a three-dimensional array. The other 1-hydroxyimidazole compounds, (6: X = 4-Br) and(6: X = 4-F), have similar structures, which differ from that of (6: X = 2-O 2 N). In (6: X = 4-Br) and (6: X = 4-F), pairs of classical O-H···N hydrogen bonds link molecules into symmetric dimers: these dimers are further stabilized by π···π interactions. Other intermolecular interactions found in both (6: X = 4-Br) and (6: X = 4-F) are C-H···O hydrogen bond and N-O···π interactions, which link the O-H···N hydrogen bonded dimers into a 3-dimensional array.

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Article Synthesis and Trypanocidal Activity of Novel 2,4,5-Triaryl-N-Hydroxylimidazole Derivatives

Cited by 26 publications

References 22 publications

Synthesis and study of prototropic tautomerism of 2-(2-hydroxyphenyl)-1-hydroxyimidazoles

Synthesis and study of prototropic tautomerism of 2-(2-hydroxyphenyl)-1-hydroxyimidazoles

Hydrazone Derivatives Enhance Antileishmanial Activity of Thiochroman-4-ones

Crystal structures of 1-hydroxylimidazole and imidazole 1-oxide derivatives

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