Synthetic studies on indoles and related compounds. <b>XXXI</b>. Chemical confirmation of the synthetic route for the benz[<i>f</i>]indole skeleton and its application

Watanabe, Tetsu; Miyagi, Chiemi; Murakami, Yasuoki

doi:10.1002/jhet.5570300137

Cited by 12 publications

(3 citation statements)

References 10 publications

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“…When incorporated in place of indole in tryptophan, the linear benz[ f ]indole moiety offers the best mimic of the side-chain conformation and planar ring system of tryptophan. Recent syntheses of benz[ f ]indole are long synthetic routes. , Batcho and Leimgruber reported a general, mild, two-step process for indole synthesis from 2-methylnitrobenzenes by condensation with formamide acetals followed by reduction. We have adapted this method to synthesize benz[ f ]indole.…”

Section: Resultsmentioning

confidence: 99%

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Fluorescence Properties of Benz[f]indole, a Wavelength and Quenching Selective Tryptophan Analog

Liu¹,

Barkley²,

Morales³

et al. 2000

J. Phys. Chem. B

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Tryptophan analogues with unique spectral and photophysical properties offer intrinsic fluorescent probes for studying peptide-protein and protein-protein interactions. Two benzannulated indole derivatives, benz-[f]indole and 3-methylbenz[f]indole, were synthesized and their fluorescence was characterized. The absorption and fluorescence emission spectra are red shifted about 75 nm to the red of the spectra of indole and 3-methylindole. INDO/S-CIS computations indicate two nearly degenerate lowest excited singlet states, analogous to the 1 L a and 1 L b transitions of indoles but with almost collinear transition moments. The limiting excitation anisotropy spectra increase and the emission anisotropy spectra decrease with increasing wavelength, probably due to vibronic coupling of the 1 L a state with higher energy B states. Solvent and temperature effects on the wavelength of maximum emission argue that emission occurs from 1 L a in polar environments. The fluorescence quantum yields and lifetimes are high and essentially independent of temperature and solvent isotope. Quantum yields are 0.80 for both compounds. Lifetimes are 19 ns for benz[f]indole and 25 ns for 3-methylbenz[f]indole. The fluorescence is not quenched by most protein functional groups in Stern-Volmer experiments, though it is quenched weakly by strong electron acceptors, such as histidine and cysteine. These results indicate that two nonradiative processes of indoles, solvent quenching and excited-state proton transfer, are not important decay pathways of benzannulated indoles. A third nonradiative process, excited-state electron transfer, occurs in benzannulated indoles under more limited conditions than in indoles.

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Section: Resultsmentioning

confidence: 99%

“…Recent syntheses of benz[f]indole are long synthetic routes. 17, 18 Batcho and Leimgruber 19 reported a general, mild, two-step process for indole synthesis from 2-methylnitrobenzenes by condensation with formamide acetals followed by reduction. We have adapted this method to synthesize benz[f]indole.…”

Section: Resultsmentioning

confidence: 99%

Fluorescence Properties of Benz[f]indole, a Wavelength and Quenching Selective Tryptophan Analog

Liu¹,

Barkley²,

Morales³

et al. 2000

J. Phys. Chem. B

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“…Compounds 5 , 7 , 8 , 8c , 8d , , 11 , 12 , 12a , 13 , 14 , 15 , 16 , and 36 were prepared as described.…”

Section: Experimental Sectionmentioning

confidence: 99%

Synthesis and Structure–Activity Relationships of Lapacho Analogues. 2. Modification of the Basic Naphtho[2,3-b]furan-4,9-dione, Redox Activation, and Suppression of Human Keratinocyte Hyperproliferation by 8-Hydroxynaphtho[2,3-b]thiophene-4,9-diones

et al. 2014

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The basic structure of linearly anellated lapacho quinones, naphtho[2,3-b]furan-4,9-dione (7), was modified in the search for novel agents against keratinocyte hyperproliferation. The synthesis and structure-activity relationships of several heterocycle-fused naphthoquinones as well as a full range of 2- and 7-substituted derivatives of one of these, 8-hydroxynaphtho[2,3-b]thiophene-4,9-dione (8a), are described. Out of a total of 71 analogues, particularly 2-thenoyl-substituted 26l, 2-nicotinoyl-substituted 26m, and 2-oxadiazole-substituted 35a compared favorably with the antipsoriatic agent anthralin. Their potency for suppression of keratinocyte hyperproliferation, which was evaluated using HaCaT cells as a model, was combined with comparably low membrane-damaging effects toward keratinocytes, as established by the release of lactate dehydrogenase activity from the cytoplasm of the cells. With respect to the mechanism of action, redox activation of lapacho quinones by one- and two-electron reduction in isolated enzymatic assays was studied, and their potential to generate superoxide was confirmed in the keratinocyte-based hyperproliferation assay.

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ChemInform Abstract: Synthetic Studies on Indoles and Related Compounds. Part 31. Chemical Confirmation of the Synthetic Route for the Benz(f)indole Skeleton and Its Application.

1993

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Synthetic studies on indoles and related compounds. XXXI. Chemical confirmation of the synthetic route for the benz[f]indole skeleton and its application

Cited by 12 publications

References 10 publications

Fluorescence Properties of Benz[f]indole, a Wavelength and Quenching Selective Tryptophan Analog

Fluorescence Properties of Benz[f]indole, a Wavelength and Quenching Selective Tryptophan Analog

Synthesis and Structure–Activity Relationships of Lapacho Analogues. 2. Modification of the Basic Naphtho[2,3-b]furan-4,9-dione, Redox Activation, and Suppression of Human Keratinocyte Hyperproliferation by 8-Hydroxynaphtho[2,3-b]thiophene-4,9-diones

ChemInform Abstract: Synthetic Studies on Indoles and Related Compounds. Part 31. Chemical Confirmation of the Synthetic Route for the Benz(f)indole Skeleton and Its Application.

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