Effects of Curcuminoid Pyrazoles on Cancer Cells and on the Expression of Telomerase Related Genes

Martí‐Centelles, Rosa; Falomir, Eva; Cardá, Miguel; Nieto, Carla I.; Cornago, Pilar; Claramunt, Rosa M.

doi:10.1002/ardp.201600067

Cited by 10 publications

(6 citation statements)

References 25 publications

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“…A compilation of structures of fluorinated pyrazoles, their activities, and the corresponding references during the last 5 years are provided in Figure . − …”

Section: Applications Of Fluorinated Pyrazolesmentioning

confidence: 99%

Fluorinated Pyrazoles: From Synthesis to Applications

2020

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Fluorinated pyrazoles play an important role in medicinal chemistry, drug discovery, agrochemistry, coordination chemistry, and organometallic chemistry. Since the early 1990s, their popularity has grown exponentially. Moreover, more than 50% of all contributions on the topic have been published in the last 5 years. In this review, analysis of novel synthetic approaches to fluorinated pyrazoles that appeared in recent years is performed. A particular emphasis is devoted to a detailed consideration of reaction mechanisms. In addition, the reasons that have led to the ever-increasing popularity of fluorinated pyrazoles in various areas of science are discussed. At the end of the review, several potentially interesting but yet mostly unknown classes of fluorinated pyrazoles are outlined.

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“…A compilation of structures of fluorinated pyrazoles, their activities, and the corresponding references during the last 5 years are provided in Figure . − …”

Section: Applications Of Fluorinated Pyrazolesmentioning

confidence: 99%

Fluorinated Pyrazoles: From Synthesis to Applications

2020

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“…In the past few years, we have been interested in preparing compounds that could be used to treat Alzheimer's disease (Martínez, 2010) and other neurodegenerative pathologies (Nieto et al, 2015;Martí-Centelles et al, 2016). Recently, two compounds, namely J147 (Chen et al, 2011;Prior et al, 2014;Daugherty et al, 2017) and CAD-31 {N-(2,4-dimethylphenyl)-2,2,2-trifluoro-N 0 -[3-(trifluoromethoxy)benzylidene]acetohydrazide; Prior et al, 2016;Daugherty et al, 2017}, have Relationship between J147, CAD-31 and 1,4-diaryl-5-trifluoromethyl-1H-1,2,3-triazoles.…”

Section: Introductionmentioning

confidence: 99%

The structures of 1,4-diaryl-5-trifluoromethyl-1H-1,2,3-triazoles related to J147, a drug for treating Alzheimer's disease

et al. 2018

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J147 [N-(2,4-dimethylphenyl)-2,2,2-trifluoro-N'-(3-methoxybenzylidene)acetohydrazide] has recently been reported as a promising new drug for the treatment of Alzheimer's disease. The X-ray structures of seven new 1,4-diaryl-5-trifluoromethyl-1H-1,2,3-triazoles, namely 1-(3,4-dimethylphenyl)-4-phenyl-5-trifluoromethyl-1H-1,2,3-triazole (CHFN, 1), 1-(3,4-dimethylphenyl)-4-(3-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (CHFNO, 2), 1-(3,4-dimethylphenyl)-4-(4-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (CHFNO, 3), 1-(2,4-dimethylphenyl)-4-(4-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (CHFNO, 4), 1-[2,4-bis(trifluoromethyl)phenyl]-4-(3-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (CHFNO, 5), 1-(3,4-dimethoxyphenyl)-4-(3,4-dimethoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (CHFNO, 6) and 3-[4-(3,4-dimethoxyphenyl)-5-(trifluoromethyl)-1H-1,2,3-triazol-1-yl]phenol (CHFNO, 7), have been determined and compared to that of J147. B3LYP/6-311++G(d,p) calculations have been performed to determine the potential surface and molecular electrostatic potential (MEP) of J147, and to examine the correlation between hydrazone J147 and the 1,2,3-triazoles, both bearing a CF substituent. Using MEPs, it was found that the minimum-energy conformation of 4, which is nearly identical to its X-ray structure, is closely related to one of the J147 seven minima.

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“…The effect of modification of the dicarbonyl fragment into the pyrazole fragment on the bioactivity of diarylpentenediones has been studied by Caldarelli et al 106 In their article the authors have reported the synthesis of several unsymmetric C5-curcuminoids (diarylpentenediones) 1 and their corresponding pyrazoles 83 and their cytotoxicity against human melanoma cell lines (MeWo) (Table 4). An extensive study into the biological properties of styrylpyrazoles has been conducted by Claramunt et al ., 107 Nieto et al ., 108,109 and Marti-Centeles et al 110 A short summary of these works can be found in Section 3 of the present review.…”

Section: Reactivitymentioning

confidence: 91%