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Open AccessArticle

Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits—Synthesis and Antitumor Activity

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Department of Organic Chemistry, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, 4 Jagiellońska Str., 41-200 Sosnowiec, Poland
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Department of Cell Biology, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, 8 Jedności Str., 41-200 Sosnowiec, Poland
*
Author to whom correspondence should be addressed.
Academic Editor: Diego Muñoz-Torrero
Molecules 2017, 22(3), 447; https://doi.org/10.3390/molecules22030447
Received: 21 January 2017 / Revised: 5 March 2017 / Accepted: 8 March 2017 / Published: 11 March 2017
(This article belongs to the Section Medicinal Chemistry)
The compounds produced by a living organism are most commonly as medicinal agents and starting materials for the preparation of new semi-synthetic derivatives. One of the largest groups of natural compounds consists of products containing a 1,4-benzoquinone subunit. This fragment occurs in three enediyne antibiotics, dynemicin A, deoxydynemicin A, and uncilamicin, which exhibit high biological activity. A series of alkoxy derivatives containing 1,4-naphthoquinone, 5,8-quinolinedione, and 2-methyl-5,8-quinolinedione moieties was synthesized. Moreover, the 1,4-benzoquinone subunit was contacted with an enediyne fragment. All obtained compounds were characterized by spectroscopy and spectrometry methods. The resulting alkane, alkene, alkyne and enediyne derivatives were tested as antitumor agents. They showed high cytotoxic activity depending on the type of 1,4-benzoquinone subunit and the employed tumor cell lines. The synthesized derivatives fulfill the Lipinski Rule of Five and have low permeability through the blood–brain barrier. View Full-Text
Keywords: alkoxy substituent; 1,4-benzoquinone; enediyne; antiproliferative activity; Lipinski Rule of Five; blood–brain barrier alkoxy substituent; 1,4-benzoquinone; enediyne; antiproliferative activity; Lipinski Rule of Five; blood–brain barrier
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MDPI and ACS Style

Kadela-Tomanek, M.; Bębenek, E.; Chrobak, E.; Latocha, M.; Boryczka, S. Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits—Synthesis and Antitumor Activity. Molecules 2017, 22, 447.

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