Synthesis of (E)-Stilbenes and (E,E)-1,4-Diphenylbuta-1,3-diene Promoted by Boron Trifluoride-Diethyl Ether Complex

Narender, Tadigoppula; Reddy, K. Papi; Madhur, G.

doi:10.1055/s-0029-1217010

Cited by 11 publications

(3 citation statements)

References 13 publications

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“…The product was extracted with CH 2 Cl 2 , dried over anhydrous MgSO 4 , and chromatographed using 1:10 CH 3 OH/CH 2 Cl 2 to afford 85 mg (43%) of 4a . Mp 184−185 °C (lit . 186 °C).…”

Section: Methodsmentioning

confidence: 99%

Fluorinated N,N-Dialkylaminostilbenes for Wnt Pathway Inhibition and Colon Cancer Repression

et al. 2011

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Colorectal cancer (CRC) is the second leading cause of cancer-related mortality in the United States. CRC is initiated by mutations of the tumor suppressor gene, adenomatous polyposis coli (APC) or β-catenin gene. These mutations stabilize β-catenin and constitutively activate Wnt/β-catenin target genes, such as c-Myc and Cyclin D1, ultimately leading to cancer. Naturally occurring stilbene derivatives, resveratrol and pterostilbene, inhibit Wnt signaling and repress CRC cell proliferation but are ineffective at concentrations lower than 10 µM. To understand the structure/activity relationship within these stilbene derivatives and to develop more efficacious Wnt inhibitors than these natural products, we synthesized and evaluated a panel of fluorinated N,N-dialkylaminostilbenes. Among this panel, (E)-4-(2,6-difluorostyryl)-N,N-dimethylaniline (4r) inhibits Wnt signaling at nanomolar levels and inhibits the growth of human CRC cell xenografts in athymic nude mice at a dosage of 20mg/kg. These fluorinated N,N-dialkylaminostilbenes appear to inhibit Wnt signaling downstream of β-catenin, probably at the transcriptional level.

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“…The product was extracted with CH 2 Cl 2 , dried over anhydrous MgSO 4 , and chromatographed using 1:10 CH 3 OH/CH 2 Cl 2 to afford 85 mg (43%) of 4a . Mp 184−185 °C (lit . 186 °C).…”

Section: Methodsmentioning

confidence: 99%

Fluorinated N,N-Dialkylaminostilbenes for Wnt Pathway Inhibition and Colon Cancer Repression

et al. 2011

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“…We selected 4-[(E)-2-phenylethenyl]phenol acetate ((E)-7) [42]. Irradiation (l > 290 nm) of a 0.12m solution of (E)-7 in oxygen-free benzene yielded (Z)-7 and the dimers 8 -11 (Scheme 4).…”

mentioning

confidence: 99%

Photo‐Cross‐Linking of Polymethacrylates with Stilbene Chromophores in the Side Chains

Jahnke

Beile

Meier

2011

Helvetica Chimica Acta

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Methacrylates (¼ 2-methylpropenoates) 5 with (E)-stilbene (¼ (E)-1,2-diphenylethene) building blocks on tethers of variable length were prepared (Scheme 2) and polymerized (i.e., 5 ! 6; Scheme 3) in the presence of AIBN (¼ 2,2'-azobis(2-methylpropanenitrile). 4-[(E)-2-Phenylethenyl]phenyl acetate (7) as model compound established the cyclodimerization as a single irreversible photoreaction. i.e., (7 ! 8 -11; Scheme 4) in the absence of oxygen. The solution photolysis of the polymers 6 provided a similar result, whereby [2p þ 2p] cycloadditions of stilbene units of neighboring tethers predominated. On the contrary, the desired photo-cross-linking of chaines occurred in the irradiation of polymer films.

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“…The conversions of p - and o -methoxybenzaldehydes in samples were evaluated by 1 H NMR spectroscopy (BRUKER DPX 300 NMR). Different proton chemical shifts of MeO-substituent (singlet) for p -methoxybenzaldeyde (reactant) and ( Z )-, ( E )-1-methoxy-4-styrylbenzene (products) may be observed: (i) ( Z )-1-methoxy-4-styrylbenzene at 3.77 ppm, (ii) ( E )-1-methoxy-4-styrylbenzene at 3.84 ppm, (iii) p -methoxybenzaldeyde at 3.88 ppm ( 1 H NMR spectra of commercial compound). Similar chemical shifts of ortho MeO-substituents may be observed.…”

Section: Methodsmentioning

confidence: 99%

Phase Transfer Catalyzed Wittig Reaction in the Microtube Reactor under Liquid–Liquid Slug-Flow Pattern

Šinkovec

Krajnc

2011

Org. Process Res. Dev.

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Phase transfer catalysis (PTC) is an important method in synthetic two-phase chemistry. Stable liquidÀliquid hydrodynamic flow in a microtube reactor offers considerable benefits over the conventional batch reactors. In this work, we attempted to conduct a two-phase organic solvent/aqueous sodium hydroxide solution PTC Wittig reaction of benzyltriphenylphosphonium bromide and oand p-methoxybenzaldehydes in a microtube reactor under reproducible slug-flow pattern. Stable operating conditions and a defined specific interfacial area are crucial to study the interaction between kinetics and mass transfer effects. A strong impact of aqueous-to-organic (AO) phase volumetric flow ratio on the specific interfacial area and consequently on mass transfer between phases was observed. The increase of the specific interfacial area causes a higher overall reaction rate at the same residence time when 0.1 M sodium hydroxide solution was used, which confirms that mass transfer has an influence on the overall reaction rate. Increasing the aqueous sodium hydroxide solution concentration at the organicÀwater interface increased mass transport. At defined conditions, when the surface-to-volume ratio and concentration of OH À ions were adequate, reaction kinetics came to be the rate-limiting step.

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Synthesis of (E)-Stilbenes and (E,E)-1,4-Diphenylbuta-1,3-diene Promoted by Boron Trifluoride-Diethyl Ether Complex

Cited by 11 publications

References 13 publications

Fluorinated N,N-Dialkylaminostilbenes for Wnt Pathway Inhibition and Colon Cancer Repression

Fluorinated N,N-Dialkylaminostilbenes for Wnt Pathway Inhibition and Colon Cancer Repression

Photo‐Cross‐Linking of Polymethacrylates with Stilbene Chromophores in the Side Chains

Phase Transfer Catalyzed Wittig Reaction in the Microtube Reactor under Liquid–Liquid Slug-Flow Pattern

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