Synthesis of selenophene derivatives as novel CHK1 inhibitors

Hong, Pao-Chiung; Chen, Li-Jung; Lai, Tzu-Yun; Yang, Huei-Yu; Chiang, Shih-Jan; Lu, Yann-Yu; Tsai, Ping-Kuei; Hsu, Hung‐Yi; Wei, Win-Yin; Liao, Chu‐Bin

doi:10.1016/j.bmcl.2010.07.034

Cited by 14 publications

(3 citation statements)

References 27 publications

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“…All proton assignments correspond to the generic molecular schemes that are provided (Figure ). Organic precursors selenophene-2-carbaldehyde, 1-(2-(3-bromophenyl)-2-oxoethyl)pyridinium iodide, ( E )-1-(pyridin-2-yl)-3-(thiophen-2-yl)prop-2-en-1-one ( P2 ), 2-(furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ( P7 ), and 4,4,5,5-tetramethyl-2-(thiophen-2-yl)-1,3,2-dioxaborolane ( P8 ) were prepared as previously reported.…”

Section: Methodsmentioning

confidence: 99%

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Direct Spectroscopic Evidence for Constituent Heteroatoms Enhancing Charge Recombination at a TiO₂−Ruthenium Dye Interface

Severin

Koivisto

et al. 2014

J. Phys. Chem. C

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A series of three bis(tridentate) cycloruthenated sensitizers with furyl, thiophene, or selenophene units attached to the cyclometalated ligand were designed to examine how chalcogen atoms effect interfacial electron transfer events that occur following the absorption of visible light by the sensitizers when attached to mesoporous titania thin films immersed in CH 3 CN electrolytes. Spectroelectrochemistry established that the Ru III/II reduction potentials were confined to the 0.954−0.965 V vs NHE range for the series and that the density of TiO 2 acceptor states were sensitizerindependent. Pulsed light excitation into the metal-to-ligand charge transfer band of the sensitized thin films resulted in rapid excited state injection, k inj > 10 8 s −1 . Charge recombination (Ru III /TiO 2 (e − ) → Ru II /TiO 2 ) rate constants were insensitive to the identity of the cyclometalated compound, yet the open circuit photovoltages were markedly lower for the compound containing selenophene. These lower photovoltages appear to be a manifestation of a 4fold-larger, second-order rate constant measured for the reaction between triiodide and TiO 2 (e − ) in the case that the selenophene comprises the donor fragment of the dye. Adduct formation between oxidized iodide(s) and the selenophene moiety of the sensitizer is implicated.

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Section: Methodsmentioning

confidence: 99%

“…A methanol/water (9:1; 60 mL) solution containing acetylpyridine (2.2 mL, 19.7 mmol), selenophene-2-carbaldehyde (3.12 g, 19.7 mmol), and potassium hydroxide (1.05 g, 29.7 mmol) was stirred at room temperature overnight. Vacuum filtration yielded 1.43 g (27.8%) of the product as a bright yellow powder.…”

Section: Methodsmentioning

confidence: 99%

Direct Spectroscopic Evidence for Constituent Heteroatoms Enhancing Charge Recombination at a TiO₂−Ruthenium Dye Interface

Severin

Koivisto

et al. 2014

J. Phys. Chem. C

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“…However, the effects of different substitution on the pyrrole moiety on the inhibition of CHK1 kinase are less. Hong et al [111] disclosed the synthesis and CHK1 kinase inhibitory activity of a series of indolin based selenophene derivatives (60 Fig. (18)).…”

Section: Chk1 Inhibitorsmentioning

confidence: 98%

Indolinones as Promising Scaffold as Kinase Inhibitors: A Review

Prakash¹,

Raja

2012

MRMC

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Kinases are probably the most important signaling enzymes, which represent about 20% of the druggable genome. Currently, more than 150 kinases are known. So, kinase inhibition therapy has become a very important area of drug research since most of our diseases are related to intra or intercellular signaling by kinases. Indole alkaloids are extensively studied for their biological activities in several pharmaceutical areas, including, for example, antitumor. Among this chemical family, indolinone displays very promising antitumor properties by inhibiting various kinase families. These small molecules have a low molecular weight and most of them bind to protein kinases competing with ATP for the ATP-binding site. This review focuses on the indolinone based drugs approved for the treatment of cancer, drugs under clinical trial and then chemical diversity of various synthetic analogues of indolinone and their metabolites as various kinase inhibitors. This review also focused on structural activity relationship (SAR), mechanisms of action and biological targets through which indolinone and its derivatives display their antitumor activity.

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Synthesis of Biologically Relevant Small Molecules Containing Selenium. Part C. Miscellaneous Biological Activities

Braga

Rafique

2014

Patai's Chemistry of Functional Groups

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Organoselenium compounds are known as antioxidants, antithyroid, antinociceptive, antidepressant, thioredoxin reductase (TrxR) mimetic agents with a variety of protective behaviors (e.g. cardioprotective, neuroprotective and hepatoprotective). In addition. they can be used as virueides, bactericides, fungicides, cytokine inducers and immunomodulators. The chemical and biological activity of organose leniumcompounds is discussed herein. The strategies and methods for the preparation of biologically relevant small molecules containing selenium are reviewed in this chapter. The unique redox properties of selenium confer catalytic activity to organoselenium compounds and influence their biological properties as well as the methods selected for their preparation. The approaches available to obtain organoselenium compounds, including reaction of elemental selenium or diselenides with different types of carbanions or reaction of organic electrophiles with selenolate anions generated by different methods, are disclosed in this chapter.

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Synthesis of selenophene derivatives as novel CHK1 inhibitors

Cited by 14 publications

References 27 publications

Direct Spectroscopic Evidence for Constituent Heteroatoms Enhancing Charge Recombination at a TiO₂−Ruthenium Dye Interface

Direct Spectroscopic Evidence for Constituent Heteroatoms Enhancing Charge Recombination at a TiO₂−Ruthenium Dye Interface

Indolinones as Promising Scaffold as Kinase Inhibitors: A Review

Synthesis of Biologically Relevant Small Molecules Containing Selenium. Part C. Miscellaneous Biological Activities

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Synthesis of selenophene derivatives as novel CHK1 inhibitors

Cited by 14 publications

References 27 publications

Direct Spectroscopic Evidence for Constituent Heteroatoms Enhancing Charge Recombination at a TiO2−Ruthenium Dye Interface

Direct Spectroscopic Evidence for Constituent Heteroatoms Enhancing Charge Recombination at a TiO2−Ruthenium Dye Interface

Indolinones as Promising Scaffold as Kinase Inhibitors: A Review

Synthesis of Biologically Relevant Small Molecules Containing Selenium. Part C. Miscellaneous Biological Activities

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Direct Spectroscopic Evidence for Constituent Heteroatoms Enhancing Charge Recombination at a TiO₂−Ruthenium Dye Interface

Direct Spectroscopic Evidence for Constituent Heteroatoms Enhancing Charge Recombination at a TiO₂−Ruthenium Dye Interface