Activation of zinc by trimethylchlorosilane. An improved procedure for the preparation of .beta.-hydroxy esters from ethyl bromoacetate and aldehydes or ketones (Reformatsky reaction)

Picotin, G.; Miginiac, Ph.

doi:10.1021/jo00230a029

Cited by 110 publications

(39 citation statements)

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“…We now report the preparation of 1,3,4-triaryl azetidinones using a Reformatsky reaction which has been adapted for microwave conditions. Previous investigations found TMCS to be superior for zinc activation 47 in…”

Section: Chemistrymentioning

confidence: 92%

Synthesis and Evaluation of Azetidinone Analogues of Combretastatin A-4 as Tubulin Targeting Agents

et al. 2010

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Section: Chemistrymentioning

confidence: 92%

Synthesis and Evaluation of Azetidinone Analogues of Combretastatin A-4 as Tubulin Targeting Agents

et al. 2010

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“…We prepared 3OHC 8 -L-HSL by coupling (R/S)-3-hydroxyoctanoic acid with L-homoserine lactone hydrobromide according to published protocols (23). (R/S)-3-hydroxyoctanoic acid was prepared by alkaline hydrolysis of the product from the Reformatsky coupling of methyl bromoacetate and hexanal (24).…”

Section: Methodsmentioning

confidence: 99%

Virulence of Burkholderia mallei Quorum-Sensing Mutants

et al. 2013

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bMany Proteobacteria use acyl-homoserine lactone-mediated quorum-sensing (QS) to activate specific sets of genes as a function of cell density. QS often controls the virulence of pathogenic species, and in fact a previous study indicated that QS was important for Burkholderia mallei mouse lung infections. To gain in-depth information on the role of QS in B. mallei virulence, we constructed and characterized a mutant of B. mallei strain GB8 that was unable to make acyl-homoserine lactones. The QS mutant showed virulence equal to that of its wild-type parent in an aerosol mouse infection model, and growth in macrophages was indistinguishable from that of the parent strain. Furthermore, we assessed the role of QS in B. mallei ATCC 23344 by constructing and characterizing a mutant strain producing AiiA, a lactonase enzyme that degrades acyl-homoserine lactones. Although acyl-homoserine lactone levels in cultures of this strain are very low, it showed full virulence. Contrary to the previous report, we conclude that QS is not required for acute B. mallei infections of mice. QS may be involved in some stage of chronic infections in the natural host of horses, or the QS genes may be remnants of the QS network in B. pseudomallei from which this host-adapted pathogen evolved.

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“…The starting 3-substituted-3-hydroxy butanoic acid ethyl esters (2a-c) were prepared via Reformatsky reaction of ethyl bromoacetate with the appropriate ketones 1a-c following previously reported methods [31][32][33] .…”

Section: General Procedures For the Synthesis Of Compounds 2a-cmentioning

confidence: 99%

Novel thiosemicarbazides induced apoptosis in human MCF-7 breast cancer cells via JNK signaling

Malki

Elbayaa

Ashour

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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In this study, novel thiosemicarbazides and 1,3,4-oxadiazoles were synthesized and evaluated for their anticancer effects on human MCF-7 breast cancer cell lines. Among the synthesized derivatives studied, compound 2-(3-(4-chlorophenyl)-3-hydroxybutanoyl)-N-phenylhydrazinecarbothioamide 4c showed the highest cytotoxicity against MCF-7 breast cancer cells as it reduced cell viability to approximately 15% compared to approximately 25% in normal breast epithelial cells. Therefore, we focused on 4c for further investigations. Our data showed that 4c induced apoptosis in MCF-7 cells which was further confirmed by TUNEL assay. Western blotting analysis showed that compound 4c up-regulated the pro-survival proteins Bax, Bad and ERK1/2, while it down-regulated anti-apoptotic proteins Bcl-2, Akt and STAT-3. Additionally, 4c induced phosphorylation of SAPK/JNK in MCF-7 cells. Pretreatment of MCF-7 cells with 10 mM of JNK inhibitor significantly reduced 4c-induced apoptosis. Molecular docking results suggested that compound 4c showed a binding pattern close to the pattern observed in the structure of the lead fragment bound to JNK1. Collectively, the data of current study suggested that the thiosemicarbazide 4c might trigger apoptosis in human MCF-7 cells by targeting JNK signaling.

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Activation of zinc by trimethylchlorosilane. An improved procedure for the preparation of .beta.-hydroxy esters from ethyl bromoacetate and aldehydes or ketones (Reformatsky reaction)

Cited by 110 publications

References 0 publications

Synthesis and Evaluation of Azetidinone Analogues of Combretastatin A-4 as Tubulin Targeting Agents

Synthesis and Evaluation of Azetidinone Analogues of Combretastatin A-4 as Tubulin Targeting Agents

Virulence of Burkholderia mallei Quorum-Sensing Mutants

Novel thiosemicarbazides induced apoptosis in human MCF-7 breast cancer cells via JNK signaling

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