Studies on the anti-psoriatic activity and spectroscopy of 10- benzylthio-anthralin and its deuterated analogs

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Abstract

Antipsoriatic anthrones are among the most commonly used topical agents for the treatment of psoriasis. 10-Arylthio-derivatives of anthralin [dithranol; 1,8-dihydroxy-9(10H)-antracenone] are of interest in the search for new antipsoriatic agents. The synthesis of 10-benzylthio-1,8-dihydroxy- 9(10H)-antracenone and its deuterated analogs is described. The application of this information to the design of novel anthrones has resulted in compounds with diminished oxygen radical generating properties which may permit a separation of antipsoriatic and inflammatory effects. The structures of these compounds were confirmed on the basis of 13C NMR and DEPT experiment studies, which also led to the revised assignment of the 1H NMR spectrum. The compounds were evaluated for their ability to inhibit the growth of the human keratinocyte cell line HaCaT. Biological tests showed that 10-benzylthio-1,8-dihydroxy-9(10H)-antracenone slightly inhibited the HaCaT cells.

Original languageEnglish
Pages (from-to)267-276
Number of pages10
JournalChinese Pharmaceutical Journal
Volume50
Issue number5
Publication statusPublished - Oct 1998
Externally publishedYes

Fingerprint

Anthracenes
Anthralin
Spectrum Analysis
Nuclear magnetic resonance
Spectroscopy
Keratinocytes
Psoriasis
Reactive Oxygen Species
Cells
Derivatives
Cell Line
Oxygen
Growth
Experiments

Keywords

  • Anthralin
  • Anthrone
  • Antipsoriatic agents
  • DEPT experiment
  • HaCaT cells
  • Inflammatory effect
  • Keratinocyte cells
  • Psoriasis

ASJC Scopus subject areas

  • Bioengineering
  • Pharmaceutical Science

Cite this

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title = "Studies on the anti-psoriatic activity and spectroscopy of 10- benzylthio-anthralin and its deuterated analogs",
abstract = "Antipsoriatic anthrones are among the most commonly used topical agents for the treatment of psoriasis. 10-Arylthio-derivatives of anthralin [dithranol; 1,8-dihydroxy-9(10H)-antracenone] are of interest in the search for new antipsoriatic agents. The synthesis of 10-benzylthio-1,8-dihydroxy- 9(10H)-antracenone and its deuterated analogs is described. The application of this information to the design of novel anthrones has resulted in compounds with diminished oxygen radical generating properties which may permit a separation of antipsoriatic and inflammatory effects. The structures of these compounds were confirmed on the basis of 13C NMR and DEPT experiment studies, which also led to the revised assignment of the 1H NMR spectrum. The compounds were evaluated for their ability to inhibit the growth of the human keratinocyte cell line HaCaT. Biological tests showed that 10-benzylthio-1,8-dihydroxy-9(10H)-antracenone slightly inhibited the HaCaT cells.",
keywords = "Anthralin, Anthrone, Antipsoriatic agents, DEPT experiment, HaCaT cells, Inflammatory effect, Keratinocyte cells, Psoriasis",
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AB - Antipsoriatic anthrones are among the most commonly used topical agents for the treatment of psoriasis. 10-Arylthio-derivatives of anthralin [dithranol; 1,8-dihydroxy-9(10H)-antracenone] are of interest in the search for new antipsoriatic agents. The synthesis of 10-benzylthio-1,8-dihydroxy- 9(10H)-antracenone and its deuterated analogs is described. The application of this information to the design of novel anthrones has resulted in compounds with diminished oxygen radical generating properties which may permit a separation of antipsoriatic and inflammatory effects. The structures of these compounds were confirmed on the basis of 13C NMR and DEPT experiment studies, which also led to the revised assignment of the 1H NMR spectrum. The compounds were evaluated for their ability to inhibit the growth of the human keratinocyte cell line HaCaT. Biological tests showed that 10-benzylthio-1,8-dihydroxy-9(10H)-antracenone slightly inhibited the HaCaT cells.

KW - Anthralin

KW - Anthrone

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KW - Inflammatory effect

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KW - Psoriasis

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