Synthesis and antifungal activity of a new series of 2-(1H-imidazol-1-yl)-1-phenylethanol derivatives

Vita, Daniela De; Scipione, Luigi; Tortorella, Silvano; Mellini, Paolo; Rienzo, Brunella Di; Simonetti, Giovanna; D’Auria, Felicia Diodata; Panella, Simona; Cirilli, Roberto; Santo, Roberto Di; Palamara, Anna Teresa

doi:10.1016/j.ejmech.2012.01.034

Cited by 41 publications

(41 citation statements)

References 23 publications

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“…Imidazole-based compounds exhibit diverse biological activities anticancer [2][3][4][5] antibacterial [6,7], antitubercular [8,9], antifungal [10,11], antiviral [12][13][14], anticonvulsant [15][16][17] and antiparkinson's agents [18,19]. The [20][21][22]. In addition, a literature search revealed that a plethora of bioactive molecules incorporate the 1,3-benzodioxole scaffold in their structure [23][24][25].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C₁₃H₁₂N₂O₃

Al-Wabli

Al-Ghamdi

Ghabbour

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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C 13 H 12 N 2 O 3 , monoclinic, P21/n (no. 14), a = 7.3322(5) Å, CCDC no.: 1513740The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of materialA mixture of 1-(2H-1,3-benzodioxol-5-yl)ethanone (3.28 g, 20 mmol), dimethylamine hydrochloride (2.20 g, 27 mmol),

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Section: Discussionmentioning

confidence: 99%

Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C₁₃H₁₂N₂O₃

Al-Wabli

Al-Ghamdi

Ghabbour

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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“…In recent years, the second generation of triazoles, which are still under construction, seems to have a broader spectrum of activity and appear to be more effective than their predecessors (De Vita et al, 2012). Today, it is currently accepted that imidazoles and triazoles are the most effective agents for the treatment of fungal infections (De Vita et al, 2012;Kathiravan et al, 2012), and consequently novel azole formulations are still being researched and developed (Rezaei et al, 2011). The aim of this study was to evaluate two new imidazoles synthesized from naphthoquinone b-lapachone on C. albicans viability, dimorphism and on the biofilm produced by this yeast.…”

Section: Introductionmentioning

confidence: 99%

3-Indol carboxaldehyde, an imidazole synthesized from naphthoquinone β-lapachone downregulates Candida albicans biofilm

et al. 2014

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Candida species can cause infections that range from superficial to life-threatening events. Candida albicans is an opportunistic pathogen of human microbiota, and it is frequently described as a commensal organism, but in many cases, it can assume a pathogenic behavior. The increasing number of immunocompromised patients has promoted an increase in the incidence of microorganisms that are resistant to conventional therapy. Additionally, the limited number of antifungal drugs has made the search for new compounds extremely relevant. In this study, we determined the minimal inhibitory concentrations (MICs) of two synthetic imidazoles derived from b-lapachone, namely 3-indol carboxaldehyde and p-N(CH 3 )2-benzaldehyde against a clinical isolate of C. albicans resistant to fluconazole and the reference strain ATCC 10231. Both strains had their growth affected by 3-indol carboxaldehyde, and the MICs were calculated as 31.7 and 41 lg ml -1 for ATCC 10231 and the clinical isolate, respectively. However, the p-N(CH 3 )2-benzaldehyde MIC values were above 100 lg ml -1 for both strains. Morphogenesis assays revealed that 3-indol carboxaldehyde inhibited significantly the germ tube transformation process. Moreover, this azole was also able to interfere significantly with biofilm formation of both strains, and also demonstrated the ability to disaggregate mature biofilms. The results obtained in this study indicate that 3-indol carboxaldehyde may be considered a viable alternative in modulating C. albicans biofilm and viability.

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confidence: 99%

“…9,10 Moreover, recent studies demonstrated that N-heterocyclic rings can be effectively replaced by 3-pyridyl or 4-pyridyl moieties. 11−13 We have selected eight compounds available from our laboratory library: racemic 1-imidazolyl-2-phenylethanol derivatives 14 (1−5) (Figure 1) and new 4-aminopyridines (6−8) (Scheme 1). Compounds 1−5 belonging to azole class have been chosen for their structural similarity with CYP51 Tc inhibitors; the new 4-aminopyridines (6−8), second generation compounds, have been selected for the presence of the N-4-pyridyl moiety able to interact with the CYP51 Tc active site, as previously reported.…”

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New Promising Compounds with in Vitro Nanomolar Activity against Trypanosoma cruzi

Friggeri

Scipione

Costi

et al. 2013

ACS Med. Chem. Lett.

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ABSTRACT:The antiparasitic activity of azole and new 4-aminopyridine derivatives has been investigated. The imidazoles 1 and 3−5 showed a potent in vitro antichagasic activity with IC 50 values in the low nanomolar concentration range. The (S)-1, (S)-3, and (S)-5 enantiomers showed (up to) a thousand-fold higher activity than the reference drug benznidazole and furthermore low cytotoxicity on rat myogenic L6 cells. KEYWORDS:Trypanosoma cruzi, CYP51, antiparasitic activity, Chagas disease, azole, aminopyridine C hagas disease (CD) is one of the most important neglected tropical disorders, caused by the Kinetoplastid parasite Trypanosoma cruzi, 1 and approximately 10 million people worldwide are estimated to be infected. 2 CD is a complex anthropozoonosis transmitted to humans by bloodsucking insects of the Triatominae subfamily (mainly Triatoma infestans, Rhodnius prolixus, and Triatoma dimidiatae). 3 Currently, the treatment of CD is restricted to nifurtimox and benznidazole used only in the acute phase. The clinical efficacy in chronic patients is limited and controversial, and the undesirable side effects of both drugs are a major drawback in their use. 4,5 To date, posaconazole and E1224, a pro-drug of ravuconazole, are in phase 2 of clinical trials for chronic Chagas disease treatment. 6 However, the development of new effective and safe drugs is urgent because of the lack of vaccines, the inadequate chemotherapy, the large number of infected people, and their migration toward nonendemic countries.Similar to fungi and yeasts, Kinetoplastides are strictly dependent on endogenously produced sterols, essential cellular components, that modulate membrane fluidity/permeability and also play multiple regulatory functions related to cell division, growth, and developmental processes. Sterol 14α-demethylase (CYP51) is an essential enzyme in sterol biosynthesis and its inhibition causes the block of sterol production and the accumulation of toxic methylated sterol precursors followed by pathogen growth arrest and death. 7,8 For these reasons, CYP51 of T. cruzi (CYP51 Tc ) is a highly drug-targetable enzyme for the rational design of new antitrypanosomal drugs. Currently, antifungal azoles (i.e., ketoconazole, fluconazole, posaconazole, and voriconazole) are known as CYP51 Tc inhibitors due to the presence of an imidazole or triazole ring able to coordinate the heme-iron. 9,10 Moreover, recent studies demonstrated that N-heterocyclic rings can be effectively replaced by 3-pyridyl or 4-pyridyl moieties. 11−13 We have selected eight compounds available from our laboratory library: racemic 1-imidazolyl-2-phenylethanol derivatives 14

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Synthesis and antifungal activity of a new series of 2-(1H-imidazol-1-yl)-1-phenylethanol derivatives

Cited by 41 publications

References 23 publications

Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C₁₃H₁₂N₂O₃

Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C₁₃H₁₂N₂O₃

3-Indol carboxaldehyde, an imidazole synthesized from naphthoquinone β-lapachone downregulates Candida albicans biofilm

New Promising Compounds with in Vitro Nanomolar Activity against Trypanosoma cruzi

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Synthesis and antifungal activity of a new series of 2-(1H-imidazol-1-yl)-1-phenylethanol derivatives

Cited by 41 publications

References 23 publications

Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C13H12N2O3

Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C13H12N2O3

3-Indol carboxaldehyde, an imidazole synthesized from naphthoquinone β-lapachone downregulates Candida albicans biofilm

New Promising Compounds with in Vitro Nanomolar Activity against Trypanosoma cruzi

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Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C₁₃H₁₂N₂O₃

Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C₁₃H₁₂N₂O₃