Isoflavone derivatives, and salts thereof, and cancerocidal and

Details Isoflavone derivatives, and salts thereof, and cancerocidal and Isoflavone derivatives, and salts thereof, and cancerocidal and

1987-07-16

1989-06-20

Chan, Nicky

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549403, C07D31124

Patent

active

048410772

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention relates to new isoflavone derivatives and salts thereof having cancerocidal and immunosuppressive activity.


BACKGROUND OF THE INVENTION

We formerly found a cancerocidal substance in the product of Pseudomonus sp. YO-0170 strain (FERM-P8170) during a study in search for cancerocidal substances produced by microorganisms, identified it as genistein (chemical name: 5,7,4'-trihydroxyisoflavone,)--a compound reported in J.A.C.S. (on page 3447, 1951)--, and filed patent application on the manufacturing process of this compound and anticancer agents containing the same (Japanese Patent Publication No. 88235 and No. 89770, 1985).
The above paper reports that genistein has weak estrogenic action, but nothing is known about the cancerocidal and immunosuppressive activity of this compound.


DISCLOSURE OF THE INVENTION

A primary object of this invention is to provide useful compounds having cancerocidal and immunosuppressive activity. A further object of this invention is to provide useful compounds having inhibitory actions against tyrosine-specific protein kinase activity and against the growth of tumor cells, as well as imunosuppressive action. Another object of this invention is to provide drugs of low toxicity having cancerocidal and immunosuppressive activity.
In search for substances showing cancerocidal and immunosuppressive actions, we synthesized various compounds having isoflavone skeleton and found, after screening tests, that the new isoflavone derivatives represented by the general formula (I) and salts thereof exhibit inhibitory action against tyrosine-specific protein kinase activity and immunosupressive action and hence are useful as cancerocidal and immunosupressive agents. This invention was accomplished based on these findings.
Thus this invention relates to new isoflavone derivatives represented by the general formula (I) and salts thereof and to new cancerocidal and immunosuppressive agents containing the same; ##STR2## wherein R.sup.1 is a radical of a radical of -CONHR.sup.5, a radical of -A-S-R.sup.6, or a radical of -COOR.sup.7 ; A denotes a lower alkylene group; R.sup.3 and R.sup.4 are each a hydrogen atom, a lower alkyl, a cycloalkyl or a sulfur- and nitrogen-containing 5- or 6-membered heterocyclic groups which groups may optionally be substituted by one or two hydroxyl groups, or R.sup.3 and R.sup.4 may be taken together to form, in conjunction with the adjacent nitrogen, a pyrrolidine, piperidine or morpholine ring; R.sup.5 stands for hydrogen atom or a lower alkyl which may be substituted by one or two hydroxyl groups; R.sup.6 represents a lower alkyl or a sulfur- and nitrogen containing 5- or 6-membered heterocyclic radical which may optionally be substituted by one or two hydroxyl, carboxyl, or lower alkoxycarbonyl groups; R.sup.7 is a lower alkyl which may be substituted by one or two hydroxyl or lower alkoxy groups (a lower alkyl having a carbon number of 1 or 3 through 6, or a lower alkyl substituted by one or two hydroxyl or lower alkoxy groups, when R.sup.2 is hydroxyl or a lower alkoxy group); and R.sup.2 is hydroxyl, a lower alkoxy or an acyloxy group.
Unless otherwise specified, the term "lower" herein means a linear or branched chain of 1 to 6 carbon atoms. Hence, "lower alkyl radicals" represent linear or branched alkyl groups of 1 to 6 carbon atoms, illustrative examples including methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tertpentyl, 1-methylbutyl, 2-methylbutyl, 1,2-dimethylpropyl; 1-ethylpropyl, hexyl, isohexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 1-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-2-methylpropyl and 1-ethyl-1-methylpropyl.
As examples of "lower alkoxy radicals" there may be mentioned linear and branched alkoxy groups of 1 to 6 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy, h

REFERENCES:
patent: 3352754 (1967-11-01), Gazave
Edwards, J. Natural Products, 42, 85-91 (1979).
Szabo et al., C.A., 83, 178,724r (1975).

Affiliated with

Also associated with

Rating

Isoflavone derivatives, and salts thereof, and cancerocidal and does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Isoflavone derivatives, and salts thereof, and cancerocidal and , we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Isoflavone derivatives, and salts thereof, and cancerocidal and will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-526415