Compounds of the anthraquinone series

Details Compounds of the anthraquinone series Compounds of the anthraquinone series

1990-02-26

1991-03-05

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Polycyclo ring system containing anthracene configured ring...

552290, C07C14936

Patent

active

049979612

ABSTRACT:
Anthralin analogues containing a thio-substituent, especially in one or more of the positions 2-, 7- and 10- of the anthralin ring. They may be made by reacting an anthralin derivative (e.g. 10-bromoanthralin) with a thiol or a compound containing a group convertible to a thio-group. Alternatively, a 1,8-dihydroxy anthraquinone containing a thio-substituent may be reduced. Reactive intermediates may be made by introducing one or more nuclear allylic groups into a 1,8-dihydroxy anthraquinone and then converting them into a reactive form, e.g. by epoxydation or halide addition. The intermediate can then be reduced to the oxidation state corresponding to anthralin.
Additional compounds, having the 10-carbon atom of the anthralin ring as part of a heterocyclic ring, may be made by oxidising anthralins containing various substituted thioalkyl groups as the 10-substituent.
The compounds are useful for treatment of psoriasis, and may be formulated in the conventional vehicles for topical application, especially petrolatum.

REFERENCES:
Synthesis, Journal of Synthetic Organic Chemistry, No. 5, May 1986 (Stuttgart DE), M.d'Ischia et al.: "Synthesis of 10-Alkylthio-and Arylthio-1,8-Dihydroxy-9-Anthrone, a New Class of Anthracene Derivatives of Potential Pharmacological Interest", pp. 430-431.

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