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3 results on '"Aquayamycin"'

1. λ3-Iodane-mediated arenol dearomatization. Synthesis of five-membered ring-containing analogues of the aquayamycin ABC tricyclic unit and novel access to the apoptosis inducer menadione

Author

Lebrasseur, Nathalie, Fan, Gao-Jun, Oxoby, Mayalen, Looney, Matthew A., and Quideau, Stéphane

Subjects
*AROMATIC compounds, *RING formation (Chemistry), *NAPHTHALENE, *CANCER cells
Abstract

Abstract: The λ3-iodane [bis(trifluoroacetoxy)]iodobenzene (BTI)-mediated oxidative dearomatization of 2-alkoxyarenols with soft external carbon-based nucleophiles constitutes a rapid access to highly functionalized naphthoid cyclohexa-2,4-dienones. These synthons can serve as valuable intermediates in the construction of the angularly-oxygenated benz[a]naphthalene ABC ring system of aquayamycin- and SS-228Y-type antibiotic angucyclinones, and analogues thereof. This methodology led to the elaboration of five-membered A ring-containing analogues of this ABC tricyclic unit. In addition, the BTI-mediated oxidative activation of 2-methylnaphthol can be exploited to prepare menadione (i.e. vitamin K3), known to induce apoptosis and autoschizis, a novel type of cancer cell death. [Copyright &y& Elsevier]

Published
2005
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2. λ3-Iodane-mediated arenol dearomatization. Synthesis of five-membered ring-containing analogues of the aquayamycin ABC tricyclic unit and novel access to the apoptosis inducer menadione

Author

Nathalie Lebrasseur, Matthew A. Looney, Gao-Jun Fan, Mayalen Oxoby, and Stéphane Quideau

Subjects
chemistry.chemical_classification, Aquayamycin, Chemistry, Stereochemistry, Organic Chemistry, Synthon, Iodobenzene, Ring (chemistry), Biochemistry, chemistry.chemical_compound, Menadione, Nucleophile, Drug Discovery, Autoschizis, Tricyclic
Abstract

The λ3-iodane [bis(trifluoroacetoxy)]iodobenzene (BTI)-mediated oxidative dearomatization of 2-alkoxyarenols with soft external carbon-based nucleophiles constitutes a rapid access to highly functionalized naphthoid cyclohexa-2,4-dienones. These synthons can serve as valuable intermediates in the construction of the angularly-oxygenated benz[a]naphthalene ABC ring system of aquayamycin- and SS-228Y-type antibiotic angucyclinones, and analogues thereof. This methodology led to the elaboration of five-membered A ring-containing analogues of this ABC tricyclic unit. In addition, the BTI-mediated oxidative activation of 2-methylnaphthol can be exploited to prepare menadione (i.e. vitamin K3), known to induce apoptosis and autoschizis, a novel type of cancer cell death.

Published
2005

3. The structure of aquayamycin

Author

H. Umezawa, M. Sezaki, K. Maeda, S. Kondo, and M. Ohno

Subjects
Aquayamycin, chemistry.chemical_compound, Chemistry, chemistry, Chemical Phenomena, Organic Chemistry, Drug Discovery, Benz(a)Anthracenes, Biochemistry, Combinatorial chemistry, Derivative (chemistry), Anti-Bacterial Agents
Abstract

The structure of a new antibiotic, aquayamycin, has been established as derivative of benze[ a ]-anthracene by spectroscopic and degradative experiments.

Published
1970

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