- Synthesis and cytotoxic effect of 1,3-dihydroxy-9,10-anthraquinone derivatives
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1,3-Dihydroxy-9,10-anthraquinone (4) was reacted with epichlorohydrin or 1,ω-dibromo-alkane to yield 1-hydroxy-3-(2,3-epoxypropoxy)-9,10-anthraquinone (5) and 1-hydroxy-3-(3-chloro-2-hydroxypropoxy)-9,10-anthraquinone (6) or 1-hydroxy-3-(ω-bromoalkoxy)-9,10-anthraquinone. Ring-opening of the epoxide (5) or 1-hydroxy-3-(ω-bromoalkoxy)-9,10-anthraquinones with appropriate amines, afforded various 1-hydroxy-3-(3-alkylamino-2-hydroxypropoxy)-9,10-anthraquinones. The synthetic compounds were tested in vitro inhibition of human T-24, Hep 3B, Hep G2, SiHa, HT-3, PLC/PRF/5 and 212 cells. Almost all compounds showed significant inhibitory activity against several different cancer cell lines. Structure - activity analysis indicated epoxidation of the hydroxyanthraquinone increased cytotoxicity against tumour cells, but ring-opening of the epoxide group with amine did not enhance the cytotoxic activity. The phosphatidylserine (PS) externalization and DNA fragmentation in SiHa cells were significantly observed after 48 h incubation with selected compound 19. The results show that 19 cause cell death by apoptosis.
- Wei, Bai-Luh,Wu, Szu-Huei,Chung, Mei-Ing,Won, Shen-Jeu,Lin, Chun-Nan
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- Intrinsically thermochromic fluorans
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A Suzuki coupling strategy has been employed to access a series of novel fluorans substituted with a phenolic moiety. These fluorans display good thermochromism in methyl stearate and obviate the need for traditional complex formulations containing acidic colour developers.
- Azizian, Farid,Field, Amanda J.,Heron, B. Mark,Kilner, Colin
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supporting information; experimental part
p. 750 - 752
(2012/02/02)
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- Synthesis and Structure - Activity Relationships of Sweet 2-Benzoylbenzoic Acid Derivatives
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Twenty-four analogues of the sweet compound 2-(4-methoxybenzoyl)benzoic acid 1 were synthesized and tasted. The structure-sweet taste relationships were studied by means of principal component analysis and by comparison with the existing sweet receptor models. Three possible glucophores were identified, which could correspond to the sites B, E1, and E2 of the Tinti - Nofre model. Some similarities between this class of compounds and isovanillic sweeteners were found.
- Arnoldi, Anna,Bassoli, Angela,Borgonovo, Gigliola,Merlini, Lucio,Morini, Gabriella
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p. 2047 - 2054
(2007/10/03)
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- High molecular weight piperidine derivatives as UV stabilizers
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Substituted high molecular weight hindered spiropiperidine compounds and polymer compositions stabilized by these compounds. The spiropiperidine compounds are prepared by reacting hindered 4-piperidinone hydrochloride with an activated benzene, such as resorcinol, in an acid medium.
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