4‐Cyano‐6,7‐dimethoxycarbostyrils with Solvent‐ and pH‐Independent High Fluorescence Quantum Yields and Emission Maxima

Ahvale, Appasaheb B.; Prokopcová, Hana; Šefčovičová, Jana; Steinschifter, Waltraud; Täubl, Anna E.; Uray, Georg; Stadlbauer, W.

doi:10.1002/ejoc.200700855

Cited by 29 publications

(59 citation statements)

References 29 publications

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“…Only the absorption of the CN-substituted building block 17 is significantly shifted to longer wavelengths. The data obtained for building blocks 16 and 17 agree well with the ones reported for the pure dyes by Uray, Stadlbauer, and coworkers [15] [16]. Since these dyes are intended to be used as fluorescence donors, their fluorescence properties are important.…”

supporting

confidence: 86%

“…Quantum yields up to 0.50 and a Stokes shift of 70 nm were observed. Last year, the group reported on carbostyril 5 and derivatives of it [16]. The compound revealed a broad double maximum between 385 and 410 nm independent of the pH value (pH 1 -11).…”

mentioning

confidence: 97%

“…After having synthesized the parent carbostyrils 2, 4, and 5, they were turned into their pertinent Fmoc -Lys -OH building blocks according to Scheme 2 and following essentially the procedures published by Uray, Stadlbauer, and co-workers [15] [16]. In the alkylation reaction with BrCH 2 COOEt, we used lithium diisopropylamide (LDA) for the deprotonation instead of NaOH/CH 2 Cl 2 or K 2 CO 3 /MeCN.…”

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confidence: 99%

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Comparative Studies of Different Quinolinone Derivatives as Donors in Fluorescence‐Resonance‐Energy Transfer (FRET) – Systems in Combination with a (Bathophenanthroline)ruthenium(II) Complex as Acceptor

Kramer

Flehr

Lay

et al. 2009

Helvetica Chimica Acta

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We describe the preparation as well as a detailed photophysical study of Fmoc-amino acid building blocks carrying different carbostyril (¼ quinolin-2(1H)-one) heterocycles as donors in a FRET (fluorescence-resonance-energy transfer) system in combination with a [Ru II (bathophenanthroline)] complex (bathophenanthroline ¼ 4,7-diphenyl-1,10-phenanthroline). The efforts resulted in a clear preference for building block 16 due to its ease of synthesis (Scheme 2), its chemical robustness, and the FRET efficiency when incorporated into peptides.Introduction. -Luminescent chromophores as entities of fluorescence-resonanceenergy transfer (FRET) systems are important tools to study supramolecular interactions with a special emphasis in the realm of biomolecules like DNA, RNA, and proteins [1]. FRET Systems allow to monitor distance-dependent interactions on the molecular level, and in a real-time mode. Therefore, they are especially suited for the characterization of biochemical events both in vitro and in vivo. Meanwhile, a myriad of applications has been reported. It involves binding of ligands to their pertinent protein receptors [2], DNA -protein complexation [3], and RNA-folding and catalysis [4]. Other applications are enzyme assays based, e.g., on the Fçrster resonance-energy-transfer principle [5] and monitoring of polymerase chain reactions (PCR) [6]. The FRET technology is based on the nonemissive transfer of energy between a donor (D) and an acceptor (A) fluorophore. It decreases with r À6 , r being the distance between the donor and the acceptor [7]. A prerequisite for an efficient transfer is an intensive overlap between the emission of the donor with the absorption of the acceptor as well as the correct orientation of their dipole transition moments relative to each other. A plethora of different donor -acceptor pairs have been reported up to date, but despite the multitude of available systems, sensitivityespecially in the presence of background luminescence from matrix constituents -still remains an issue. A further concern is robustness of the applied dyes as well as the possibility to employ them in a modular way as broadly as possible via stable covalent bonds and without interference of the spectral properties of the labelled molecules.

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confidence: 86%

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confidence: 97%

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confidence: 99%

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Comparative Studies of Different Quinolinone Derivatives as Donors in Fluorescence‐Resonance‐Energy Transfer (FRET) – Systems in Combination with a (Bathophenanthroline)ruthenium(II) Complex as Acceptor

Kramer

Flehr

Lay

et al. 2009

Helvetica Chimica Acta

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“…However, another recently described method 30 allowed us to introduce the carbonitrile function at the 4-position of compound 3 under relatively mild conditions. That is by a two-step reaction, the first step is converting Cl group to the reactive tosyloxy leaving group, at the 4-position, via the reaction of compound 3 with sodium ptoluenesulfonate to give 4-tosylate 9 (Scheme 3), which was then treated with potassium cyanide to afford the 4-cyanopyranoquinolinedione 10.…”

Section: Resultsmentioning

confidence: 99%

Nucleophilic substitution and ring transformation reactions with 4-chloro-6-ethyl-3-nitropyrano[3,2-c]quinoline-2,5(6H)-dione

Hassnin¹

2012

Arkivoc

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4-Chloro-6-ethyl-3-nitropyrano[3,2-c]quinoline-2,5(6H)-dione (3) was obtained by nitration followed by chlorination of 4-hydroxypyranoquinoline-2,5-dione 1. Substitution reactions of compound 3 with various nucleophiles, namely: sodium azide, amines, thiophenol and malononitrile, led to a series of novel 4-sustituted-3-nitropyranoquinolinones. Also, nucleophilic reactions of compound 3 with hydrazine, cyanoguanidine and S-methylisothiourea, involving ring opening-ring closure of the pyranoquinolinedione nucleus, are described.

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“…在酰胺衍生物的合成研究中, 烃化反应是一种常见的修饰方法. 相关喹啉酮母体结构的烃化研究, Bordin [7] , Ukrainets [8] , Ali [9] 与 Stadlbauer [10] NaH/DMF, r.t.…”

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N-Alkylation andO-Alkylation of Ethyl 4-(4,6-Dimethoxy-pyrimidin-2-yl)-2-oxo-1,2-dihydroquinoline-3-carboxylate

李元祥¹

2013

Chin. J. Org. Chem.

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Twenty novel N-substitued and O-substitued compounds were prepared starting from ethyl 4-(4,6-dimethoxypyrimidin-2-yl)-2-oxo-1,2-dihydroquinoline-3-carboxylate. Various halogenated hydrocarbons were used as resource of alkylation and NaH as base in N,N-dimethylformamide (DMF) at room temperature. The structures of alkylation products were confirmed by 1 H NMR, IR, MS and elemental analysis. Two isomer structures were further determined by representative X-ray structures of N10 and O10. The alkylation reaction was performed in mild conditions with a total yield of 89%～98%. Among them, the main product N-alkylation was obtained in 47%～77% yield, and O-alkylation was simultaneously obtained in 21%～49% yield by a simple one-pot reaction.

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4‐Cyano‐6,7‐dimethoxycarbostyrils with Solvent‐ and pH‐Independent High Fluorescence Quantum Yields and Emission Maxima

Cited by 29 publications

References 29 publications

Comparative Studies of Different Quinolinone Derivatives as Donors in Fluorescence‐Resonance‐Energy Transfer (FRET) – Systems in Combination with a (Bathophenanthroline)ruthenium(II) Complex as Acceptor

Comparative Studies of Different Quinolinone Derivatives as Donors in Fluorescence‐Resonance‐Energy Transfer (FRET) – Systems in Combination with a (Bathophenanthroline)ruthenium(II) Complex as Acceptor

Nucleophilic substitution and ring transformation reactions with 4-chloro-6-ethyl-3-nitropyrano[3,2-c]quinoline-2,5(6H)-dione

N-Alkylation andO-Alkylation of Ethyl 4-(4,6-Dimethoxy-pyrimidin-2-yl)-2-oxo-1,2-dihydroquinoline-3-carboxylate

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