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Sci. Pharm.
Volume 69
Issue 4
10.3797/scipharm.aut-01-196
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Scientia Pharmaceutica is published by MDPI from Volume 84 Issue 3 (2016). Previous articles were published by another publisher in Open Access under a CC-BY (or CC-BY-NC-ND) licence, and they are hosted by MDPI on mdpi.com as a courtesy and upon agreement with Austrian Pharmaceutical Society (Österreichische Pharmazeutische Gesellschaft, ÖPhG).
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Article

Tetramethyltetrahydro-1,4-anthrachinonazobenzoesäure, ein 5-Lipoxygenase-Inhibitor mit zelldifferenzierender Aktivität.
Untersuchungen an 1,4-Naphthochinonen, 28. Mitt. 1)

by
G. Wurm
*,
R. Probst
and
S. Schwandt
Institut für Pharmazie der Freien Universität Berlin, Königin-Luise-Str. 2+4, D-14195 Berlin-Oahlem
*
Author to whom correspondence should be addressed.
Sci. Pharm. 2001, 69(4), 257-264; https://doi.org/10.3797/scipharm.aut-01-196
Submission received: 16 July 2001 / Accepted: 24 August 2001 / Published: 28 December 2001
Versions Notes

Abstract

The combination of 5-lipoxygenase (5-LOX) inhibition and retinoid activity in one molecule could be a suitable too1 for the topical psoriasis therapy. The anellation of the 5-LOX inhibitor 1 with the tetramethylcyclohexane moity to the arotinoid structure 2 does not fullfil this expectation. This compound was not able to differentiate HL-60 cells to granulocytes. The exchange of the 3,5-di-tertbutyl-
4-hydroxyphenyl substituent by benzoic acid and the synthesis of 8 resulted in the loss of 5-LOX inhibition also. The construction of 10 by the introduction of an azo spacer between the anthraquinone moity and benzoic acid of 8 finally led to the expected compound: 10 was potent 5-LOX inhibitor and concomitant differentiated HL-60 cells as measured by the NBT test.
Keywords: 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-1,4-anthraquinone Derivatives; Arotinoid Structure; 5-Lipoxygenase; HL-60 Differentiation 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-1,4-anthraquinone Derivatives; Arotinoid Structure; 5-Lipoxygenase; HL-60 Differentiation

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MDPI and ACS Style

Wurm, G.; Probst, R.; Schwandt, S. Tetramethyltetrahydro-1,4-anthrachinonazobenzoesäure, ein 5-Lipoxygenase-Inhibitor mit zelldifferenzierender Aktivität.
Untersuchungen an 1,4-Naphthochinonen, 28. Mitt. 1). Sci. Pharm. 2001, 69, 257-264. https://doi.org/10.3797/scipharm.aut-01-196

AMA Style

Wurm G, Probst R, Schwandt S. Tetramethyltetrahydro-1,4-anthrachinonazobenzoesäure, ein 5-Lipoxygenase-Inhibitor mit zelldifferenzierender Aktivität.
Untersuchungen an 1,4-Naphthochinonen, 28. Mitt. 1). Scientia Pharmaceutica. 2001; 69(4):257-264. https://doi.org/10.3797/scipharm.aut-01-196

Chicago/Turabian Style

Wurm, G., R. Probst, and S. Schwandt. 2001. "Tetramethyltetrahydro-1,4-anthrachinonazobenzoesäure, ein 5-Lipoxygenase-Inhibitor mit zelldifferenzierender Aktivität.
Untersuchungen an 1,4-Naphthochinonen, 28. Mitt. 1)" Scientia Pharmaceutica 69, no. 4: 257-264. https://doi.org/10.3797/scipharm.aut-01-196

APA Style

Wurm, G., Probst, R., & Schwandt, S. (2001). Tetramethyltetrahydro-1,4-anthrachinonazobenzoesäure, ein 5-Lipoxygenase-Inhibitor mit zelldifferenzierender Aktivität.
Untersuchungen an 1,4-Naphthochinonen, 28. Mitt. 1). Scientia Pharmaceutica, 69(4), 257-264. https://doi.org/10.3797/scipharm.aut-01-196

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