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Naturalne i syntetyczne pochodne 5,8-chinolinodionu wykazujące aktywność biologiczną

Kadela-Tomanek M., Chrobak E., Bębenek E., Boryczka S.

Wiadomości Chemiczne

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2017

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[Z] 71, 11-12

795--815

EN

The compounds produced by a living organisms are most commonly used as medicinal agents and starting materials to the preparation of new semi-synthetic derivatives. It is estimated that over 23% of currently used medicinal products are natural substances. Natural compounds and their semisynthetic derivatives are most often used in the treatment of cancer and the treatment of infectious diseases. One of the groups of compounds obtained from Gram-positive bacterium are 5,8-quinolinedione antibiotics, like: streptonigrin, lavendamycin and streptonigron. The all compounds exhibit high anticancer, antimicrobial and antiviral activity. Unfortunately due to high toxicity this alkaloids did not find place in the therapy. The mechanism of action depends on interaction of compounds with the nicotinamide quinone oxidoreductase 1 (NQO1). The 5,8-quinolinedione can be reduced by the NAD(P)H as a cofactor to form the semiquinone or hydroquinone intermediates. These compounds can react with oxygen yielding a regenerated 5,8-quinolinedione fragment and creating the hydroxyl radicals, which are ultimately responsible for the DNA strands cleavage. The structure–activity relationship study has shown that the most important part of the molecule is the 5,8-quinolinedione moiety. Furthermore, it was found, that the introduction of amine, hydroxyl or thiol substituents at position 6 or 7 of the 5,8-quinolinedione moiety results in an enhanced biological activity. A lot of synthetic derivatives of 5,8-quinolinediones which containing amine, alkoxyl and thiol groups at the C-6 or/and C-7 positions have been obtained during the last few years. Commonly this compounds are obtained in the reaction of 6,7-dichloro-5,8-quinolinedione with nucleophilic factor. Depending on the reaction conditions, mono- or di-substituted derivatives are obtained. Most of synthesized compounds exhibit high biological activity, like: anticancer, antibacterial, antiviral, anti-inflammatory.

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Aktywność biologiczna związków acetylenowych pochodzenia naturalnego

Kadela-Tomanek M., Chrobak E., Bębenek E., Lubczyńska A., Siudak S., Wójcik A., Otulakowska A.

Wiadomości Chemiczne

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2016

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[Z] 70, 9-10

613--632

EN

The natural acetylenic products containing at least one a carbon-carbon triple bond, are important class of compounds widely distributed in the environment. Development of spectroscopic techniques and methods for the isolation of metabolites allowed the extraction of natural acetylenic compounds. The most of these substances have been obtained from marine organisms, such as: cyanobacteria, algae and sponges. The next source of metabolites are herbal plants, which were used in the Chinese traditional medicine. A many of them show interesting biological activity. The first isolated natural compound possessing an acetylenic unit was dehydromatricaria ester, which was obtained from rhizome European goldenrod (Solidago virgaurea). To present day have been found and researched more than 2000 natural acetylenic metabolites. Due to the chemical structure, natural acetylenic compounds were divided into six groups: peptides, aromatic compounds, enediyne antibiotics, sterols, carotenoids, and poliacetylenic compounds . This article focuses natural acetylenic substances, which exhibit interesting biological properties, particularly anticancer ones. The review presents many of such metabolites, including fatty alcohols, ketones, acids, ethers, and carotenoids.

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The Reaction of Some Dithiinodiquinolines with Potassium Methoxide as a Source of 4-Quinolinones with 3-Sulfide Function

Maślankiewicz M., Bębenek E.

Polish Journal of Chemistry

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1999

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Vol. 73, nr 11

1783-1789

EN

Reaction of thioquinanthrene 1 and isothioquinanthrene 6 with 6 molar excess of potassium methoxide produces dipotassium salts 3-A and 8-A respectively, which were converted after 3'- (or 4')-alkylation followed by neutralization into 3,4'- or 3,3'-diquinolinyl sulfides 4 or 9 with total yield up to 99%. 4-Quinolinones 4 were N1-alkylated in DMSO/aqueous alkaline solution to N,S-dialkyl derivatives 5.