Eine neue Synthese von 5‐Thiaflavin‐Derivaten

Fenner, Helmut; Grauert, Rolf W.; Tessendorf, L.

doi:10.1002/ardp.19813141012

Cited by 6 publications

(2 citation statements)

References 11 publications

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“…5TF has been subject to only a few experimental studies, , even though it has interesting photophysical properties because of the structural change in the isoalloxazine moiety (due to thio substitution at the N5 position of RF). This modification leads to a hypsochromic shift in the absorption to the far-violet region as compared to native RF .…”

Section: Introductionmentioning

confidence: 99%

“…The previous theoretical analyses concentrated on the first electronically ES (S 0 → S 1 : π H → π L *), while the experimental spectrum consists of at least three separate bands. 45 5TF has been subject to only a few experimental studies, 64,65 even though it has interesting photophysical properties because of the structural change in the isoalloxazine moiety (due to thio substitution at the N5 position of RF). This modification leads to a hypsochromic shift in the absorption to the far-violet region as compared to native RF.…”

Section: Introductionmentioning

confidence: 99%

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Assessment of Franck–Condon Methods for Computing Vibrationally Broadened UV–vis Absorption Spectra of Flavin Derivatives: Riboflavin, Roseoflavin, and 5-Thioflavin

Karasulu

Götze

Thiel

2014

J. Chem. Theory Comput.

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We address the performance of the vertical and adiabatic Franck–Condon (VFC/AFC) approaches combined with time-independent or time-dependent (TI/TD) formalisms in simulating the one-photon absorption spectra of three flavin compounds with distinct structural features. Calculations were done in the gas phase and in two solvents (water, benzene) for which experimental reference measurements are available. We utilized the independent mode displaced harmonic oscillator model without or with frequency alteration (IMDHO/IMDHO-FA) and also accounted for Duschinsky mixing effects. In the initial validation on the first excited singlet state of riboflavin, the range-separated functionals, CAM-B3LYP and ωB97xD, showed the best performance, but B3LYP also gave a good compromise between peak positions and spectral topology. Large basis sets were not mandatory to obtain high-quality spectra for the selected systems. The presence of a symmetry plane facilitated the computation of vibrationally broadened spectra, since different FC variants yield similar results and the harmonic approximation holds rather well. Compared with the AFC approach, the VFC approach performed equally well or even better for all three flavins while offering several advantages, such as avoiding error-prone geometry optimization procedures on excited-state surfaces. We also explored the advantages of curvilinear displacements and of a Duschinsky treatment for the AFC spectra in cases when a rotatable group is present on the chromophore. Taken together, our findings indicate that the combination of the VFC approach with the TD formalism and the IMDHO-FA model offers the best overall performance

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Assessment of Franck–Condon Methods for Computing Vibrationally Broadened UV–vis Absorption Spectra of Flavin Derivatives: Riboflavin, Roseoflavin, and 5-Thioflavin

Karasulu

Götze

Thiel

2014

J. Chem. Theory Comput.

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Synthese und Alkylierung von 10H‐Pyrimido[5,4‐b][1,4]benzothiazinen

Fenner

Rössler

Grauert

1981

Archiv der Pharmazie

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Synthesis and Alkylation of lOH-~rimido[S,~b][l,4]benzothipzines [ 1,4]benzothiazines 8 were prepared by condensation of barbituric acids 5 with 2-aminothiophenol (7) in DMSO via the ylide 6. Compound 8 was characterized as a 1,5-dihydro system similar to the thia-isoalloxazines 1b.The structures of the alkyl derivatives isolated from a complex mixture were established by UVIVIS, 'H-NMR, IR and ESR spectroscopy. They are discussed with regard to the alkylation of pyrimidobenzothiazines which carry substituents at N-10.In friiheren Mitteilungen uber die Eigenschaften von Pyrimido [5,4-b][ 1,4]benzothiazin-Derivaten wurde die Strukturverwandtschaft dieser Tricyclen mit den Redoxsystemen der Flavine und der Phenothiazine di~kutiert~.~). Inzwischen haben wir an entsprechend substituierten Pyrimidobenzothiazinen, z.B. einem Chlorpromazin-Analogen'), den Aspekt der Phenothiazin-Ahnlichkeit naher untersucht. Ein Vergleich der Eigenschaften von Pyrimidobenzothiazinen und Flavinen zeigt, dal3 die Flavin-Analogie auf die Dihydround Radikalstufe beschrankt ist, wahrend das dem Flavochinon 2a entsprechende Thiazoniumkation 2b unter biologisch relevanten Bedingungen keine Stabilitat aufweists).Fur das System eines ,,Thiaflavins" l b gilt jedoch die Voraussetzung, daR die N( 10)-Position einen Alkyl-bzw. Ribityl-Substituenten tragt, also eine zum Dihydroisoalloxazin l a analoge Struktur vorliegt. In der Flavin-Reihe bestehen zwischen Ispalloxazinen (la und 2a) und Alloxazinen (3a und 4a) grundlegende Unterschiede in der Reaktivitat und Stabilitat der verschiedenen Redox-Stufen') -wir haben daher zur weiteren Klarung der Strukturspezifitat des Thiaflavin-Redoxsystems die Eigenschaften des Thiaalloxazins 3b sowie das Lumichrom-Analoge 4b ausfuhrlich untersucht und die an Redoxreaktionen von 3b beteiligten Strukturen

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Pyrimido[5,4‐b]quinolines by Trialkylphosphite‐Cyclisation of 2‐Nitro‐6′‐benzylpyrimidindiones

Fenner

Hentzsch

Wiegreffe

1986

Archiv der Pharmazie

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Ein von uns berichtetes Syntheseverfahrenw4) fur 10-Deazaalloxazine 1 verlauft iiber eine cyclisierungsfahige 2-Amino-5'-brom-6'-benzylpyrimidindion-Vorstufe, die nur geringe Variationsmoglichkeiten der Substitution am Deazaflavin-System bietet. Im Rahmen von Untersuchungen zur Synthese von 10-Deaza-isoalloxazinen 2 , in denen im Falle einer Blockierung der 10-Position eine mit dem Flavin-Redoxsystem vergleichbare 1,5-azachinoide Struktur enthalten ist, haben wir auch Cyclisierungsreaktionen untersucht, die sich in Bezug auf die substituierten Pyrimidindion-Vorstufe 03654233/86/040'W)379 $ 02.50/0 0 VCH Verlagsgesellschaft mbH, D-6940 Weinheim, 1986

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Eine neue Synthese von 5‐Thiaflavin‐Derivaten

Cited by 6 publications

References 11 publications

Assessment of Franck–Condon Methods for Computing Vibrationally Broadened UV–vis Absorption Spectra of Flavin Derivatives: Riboflavin, Roseoflavin, and 5-Thioflavin

Assessment of Franck–Condon Methods for Computing Vibrationally Broadened UV–vis Absorption Spectra of Flavin Derivatives: Riboflavin, Roseoflavin, and 5-Thioflavin

Synthese und Alkylierung von 10H‐Pyrimido[5,4‐b][1,4]benzothiazinen

Pyrimido[5,4‐b]quinolines by Trialkylphosphite‐Cyclisation of 2‐Nitro‐6′‐benzylpyrimidindiones

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