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THE SYNTHESIS OF AZOPYRIMIDINES AND THEIR METALLIZED DERIVATIVES

Date

1960-08

Journal Title

Journal ISSN

Volume Title

Publisher

ORCID

Type

Degree Level

Masters

Abstract

The production of a tumor-like proliferation by a chemical compound was first demonstrated by Fischer in 1906, by the injection of a solution of scarlet red into the ears of rabbits (1). A further impetus to chemotherapeutic investigations in cancer is credited to Von Wasserman and his associates who reported, in 1911, the inhibitory effect of subcutaneously or intravenously injected selenium and eosin in certain animal tumors (2). Following Haddow's observation that certain carcinogenic hydrocarbons possess the ability to inhibit the growth of certain tumors in animals (3), a large number of substances having a structural resemblance to these carcinogenic hydrocarbons was studied. Among such compounds that were studied was a number of azo compounds, and several of these gave evidence of a significant inhibition of growth of certain tumors in animals. The pyrimidine ring occurs as a constituent of many naturally occurring substances. In particular, it occurs in the living cell in the form of nucleic acids. Also, many important therapeutic agents, such as certain of the sulfas, barbiturates, certain vitamins, and anti-thyroid agents, contain the pyrimidine ring. Therefore, some interest has been shown in the effect that compounds of the azopyrimidine type might have on tumor growth. Toxicity to enzymes and fungi by metal chelating agents has been postulated as being due to the removal of the essential metals (4, 3, 6). Certain metal chelates themselves have been shown to be active pharmacologically, for example, as antibacterial and antitubercular agents (7, 8, 9, 10), and as antitumor agents (81). Foye et al. (U) felt that azo compounds which were capable of chelation might act as transporting agents for introducing metal ions at the site of tumor growth. The presence of the metal might be of value in inhibiting tumor growth, or it might act as an indicator of the enzyme systems involved in the process of tumor formation and growth. The present work has therefore been undertaken to prepare azopyrimidines having one or two hydroxy groups in a position ortho to the azo linkage, and to prepare metal chelates of these compounds. In an attempt to learn something of the structure of the metal chelates of these azopyrimidines, compounds were chosen which would have, other than the one or two o-hydroxy groups, no other reactive groups present which might interfere with, or take part in, the chelation.

Description

Keywords

carcinogenic hydrocarbons, metal chelating agents, azo compounds

Citation

Degree

Master of Science (M.Sc.)

Department

Pharmacy

Program

Committee

Part Of

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DOI

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