Synthesis, electrochemical studies and anticancer activity of ferrocenyl oxindoles

Silva, Bárbara V.; Ribeiro, Núbia Moura; Vargas, Maria D.; Lanznaster, Maurício; Carneiro, José Walkimar de M.; Krogh, Renata; Andricopulo, Adriano D.; Dias, Luiz C.; Pinto, Ângelo C.

doi:10.1039/c002983a

Cited by 18 publications

(7 citation statements)

References 28 publications

(22 reference statements)

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“…Isatins ( 1 , Scheme ) are heterocycles with great applicability in medicinal chemistry, and they are normally used as building blocks in the preparation of various heterocyclic systems, including quinoline and indole derivatives. Electrophilic aromatic substitution at carbons C‐5 and C‐7 of isatins can be performed, along with NH alkylations, selective reduction reactions, and condensations of the carbonyl moieties 1, 2. Natural and synthetic isatin derivatives have been reported to possess antiviral, anti‐inflammatory, anticonvulsant, anticancer, and other bioactivities 3–6…”

Section: Methodsmentioning

confidence: 99%

The mechanism of Sandmeyer's cyclization reaction by electrospray ionization mass spectrometry

Silva

Violante

Pinto

et al. 2011

Rapid Comm Mass Spectrometry

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Using electrospray ionization (tandem) mass spectrometry (ESI-MS(/MS)) spectrometric experiments, the Sandmeyer reaction was monitored on-line, and key intermediates were intercepted and characterized for the first time. The mechanistic information provided by on-line ESI-MS(/MS) is in accordance with Sandmeyer's proposal, and was made possible by coupling a microreactor on-line to the ESI ion source, which allowed reactions to be screened from 0.7-2.0 s, identifying and characterizing all intermediates that were formed and consumed during the reaction.

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Section: Methodsmentioning

confidence: 99%

The mechanism of Sandmeyer's cyclization reaction by electrospray ionization mass spectrometry

Silva

Violante

Pinto

et al. 2011

Rapid Comm Mass Spectrometry

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“…The use of ferrocene in bio-organometallic chemistry has promising applications since ferrocene is a stable non-toxic compound and has good redox properties (Fouda et al, 2007). Ferrocenyloxindoles have also been found to have anticancer (Silva et al, 2010) and antiproliferative activities (Gasser et al, 2011).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of (E)-1-(4-methoxyphenyl)ethanoneO-dehydroabietyloxime

Rao¹,

Cui²,

Zheng³

2014

Acta Cryst E

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“…An oxindole structure possessing a bicyclic aromatic heterocycle with a benzene ring fused to γ-lactam is one of the structural classes (4). Diverse derivatives based on oxindole have been reported for development of new type anticancer candidates (5)(6)(7)(8). Representative natural product possessing oxindole is spirotryprostatin A, which is well known for its anticancer activities through blockade of the G2/M progression in mouse mammary carcinoma cells (4,9).…”

Section: Introductionmentioning

confidence: 99%

An β-quaternary chiral latam derivative, YH-304 as a novel broad-spectrum anticancer agent

Hwang

Park

et al. 2016

International Journal of Oncology

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Previously, we reported that α-quaternary chiral lactam derivatives have broad spectrum anticancer activity. However, the underlying molecular mechanisms and its relevance are largely unknown. In the present study, we report progress on α-quaternary chiral lactam analogues that address this, focusing on the novel analogue YH-304 as a candidate to broadly target human cancer cells. The effect of YH-304 on cell transformation was assessed by clonogenic assay in non-small cell lung cancer cells (NSCLCs) A549 and 226B. Proapoptotic activity of YH-304 was determined by TUNEL assay and cleaved PARP, cleaved caspase-9, and Bax as markers for apoptosis. The p53-dependency and therapeutic spectrum of YH-304 was assessed by western blot analysis, real-time PCR, and cell viability assays in cells expressing endogenous wild or mutant p53. The effect of YH-304 on angiogenesis in vivo was examined by bFGF-mediated angiogenesis assay in zebrafish. Finally, the effect of YH-304 on AKT and ERK activation (phosphorylation) as a putative mechanism underlying the effect of YH-304 on bFGF-mediated angiogenesis was assessed using western blotting. We found that YH-304 significantly decreases the colony-forming activities of both A549 and 226B cells, inducing cellular apoptosis. Unlike nutlin-3 (p53 pathway activator), YH-304 did not affect the expression levels of p53 and its target gene such as p21 and thus showed p53-independent anticancer activity with broad spectrum. In addition, YH-304 inhibited bFGF-induced angiogenesis in vivo through mediating AKT and ERK signaling pathway, which plays an important role in bFGF activation and angiogenesis. Taken together, our data indicate that YH-304 may represent a novel therapeutic option for the treatment of cancer in a p53-independent manner.

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Synthesis, electrochemical studies and anticancer activity of ferrocenyl oxindoles

Cited by 18 publications

References 28 publications

The mechanism of Sandmeyer's cyclization reaction by electrospray ionization mass spectrometry

The mechanism of Sandmeyer's cyclization reaction by electrospray ionization mass spectrometry

Crystal structure of (E)-1-(4-methoxyphenyl)ethanoneO-dehydroabietyloxime

An β-quaternary chiral latam derivative, YH-304 as a novel broad-spectrum anticancer agent

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