Naphthoquinone antitumor compound and method

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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5483021, 514393, 514510, 514617, 514622, 514628, 514630, 560 45, 560 47, 560 48, A61K 31415

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057894310

ABSTRACT:
The invention provides 1,4-naphthoquinone compounds and a method for inhibiting tumor cell growth in a subject by administering such compounds. The compounds are represented by the structures: ##STR1## where R.sub.1 is lower alkyl, halogenated lower alkyl, phenyl, benzyl, phenethyl, or --(CH.sub.2).sub.m COOX where m is 2 or 3 and X is H, methyl, or ethyl; R.sub.2 is halo or NHY, where Y is hydrogen, lower alkyl, halogenated lower alkyl, hydroxylated lower alkyl, lower dialkylaminoalkyl, phenyl, benzyl, or phenethyl; R.sub.3 is lower alkyl, halogenated lower alkyl, phenyl, benzyl, phenethyl, or --(CH.sub.2).sub.m COOX, where m and X are as defined for R.sub.1 above; and R.sub.4 is hydrogen, lower alkyl, lower aminoalkyl, halogenated lower alkyl, phenyl, benzyl, or phenethyl.

REFERENCES:
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Green-Buckley, G., and Griffiths, J., "Napthoquinone Colouring Matters. J. chem. Soc., Perkin Trans 1, pp. 702-707 (1979).
Hoover, J.R.E., and Day, A.R., "Preparation of Some Imidazole Derivatives of 1,4-Naphthoquinone," J. Am. Chem. Soc. 76:4148-4152 (1954).
Lin, A.J., et al., "Quinones as Anticancer Agents: Potential Bioreductive Alkylating Agents," Cancer Chemotherap Reports Part 2 4(4):23-35 (1974).
Pickering, M.V., et al., "Synthesis and Biochemical Evaluation of Nucleosides of Naphthoquinone Heterocycles," Journal of Midicinal Chemistry 20(6):818-821 (1977).
Cleaveland et al., Biochem. Pharmacol. (1995), 49(7), 947-54, Mar. 1995.

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