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Quinones and Hydroxyquinones. Target Molecules and Building Blocks in Organic Synthesis

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (30 June 2009) | Viewed by 38013

Keywords

  • Chemistry of hypervalent iodonium organic compounds and applications in synthesis
  • Transition metals in organic synthesis
  • Chemistry of hydroxyquinones

Published Papers (3 papers)

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63 KiB  
Article
Quinones as Key Intermediates in Natural Products Synthesis. Syntheses of Bioactive Xanthones from Hypericum perforatum
by George A. Kraus and John Mengwasser
Molecules 2009, 14(8), 2857-2861; https://doi.org/10.3390/molecules14082857 - 03 Aug 2009
Cited by 15 | Viewed by 11073
Abstract
Two bioactive xanthones from Hypericum perforatum have been synthesized by direct routes. Benzo[c]xanthone 5 can be prepared from intermediate 4. Full article
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268 KiB  
Article
Synthesis and Antitumor Evaluation of Novel Bis-Triaziquone Derivatives
by Cheng Hua Huang, Hsien-Shou Kuo, Jia-Wen Liu and Yuh-Ling Lin
Molecules 2009, 14(7), 2306-2316; https://doi.org/10.3390/molecules14072306 - 29 Jun 2009
Cited by 13 | Viewed by 14475
Abstract
Aziridine-containing compounds have been of interest as anticancer agents since late 1970s. The design, synthesis and study of triaziquone (TZQ) analogues with the aim of obtaining compounds with enhanced efficacy and reduced toxicity are an ongoing research effort in our group. A series [...] Read more.
Aziridine-containing compounds have been of interest as anticancer agents since late 1970s. The design, synthesis and study of triaziquone (TZQ) analogues with the aim of obtaining compounds with enhanced efficacy and reduced toxicity are an ongoing research effort in our group. A series of bis-type TZQ derivatives has been prepared and their cytotoxic activities were investigated. The cytotoxicity of these bis-type TZQ derivatives were tested on three cancer lines, including breast cancer (BC-M1), oral cancer (OEC-M1), larynx epidermal cancer (Hep2) and one normal skin fibroblast (SF). Most of these synthetic derivatives displayed significant cytotoxic activities against human carcinoma cell lines, but weak activities against SF. Among tested analogues the bis-type TZQ derivative 1a showed lethal effects on larynx epidermal carcinoma cells (Hep2), with an LC50 value of 2.02 mM, and also weak cytotoxic activity against SF cells with an LC50 value over 10 mM for 24 hr treatment. Comparing the viability of normal fibroblast cells treated with compound 1a and TZQ, the LC50 value of the latter was 2.52 mM, indicating more toxicity than compound 1a. This significantly decreased cytotoxicity of compound 1a towards normal SF cells, while still maintaining the anticancer activity towards Hep2 cells is an interesting feature. Among the seven compounds synthesized, compound 1c has similar toxicity effects on the three cancer cell lines and SF normal cells as the TZQ monomer. Full article
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270 KiB  
Article
Brominated Thiophenes as Precursors in the Preparation of Brominated and Arylated Anthraquinones
by Thies Thiemann, Yasuko Tanaka and Jesus Iniesta
Molecules 2009, 14(3), 1013-1031; https://doi.org/10.3390/molecules14031013 - 04 Mar 2009
Cited by 13 | Viewed by 12003
Abstract
Brominated anthraquinones can be synthesized directly from bromothiophenes when these are reacted with 1,4-naphthoquinones in the presence of meta-chloroperoxybenzoic acid. The bromoanthraquinones are versatile building blocks in the preparation of arylated anthraquinones and of extended π-systems with interspersed anthraquinone units. Full article
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