Synthesis of 2-methyl-4-selenoquinazolone, 2-phenylbenzoselenazole, and its derivatives: Dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Faculty of Pure Science of Columbia UniversityChen, Yü-Gwan
Science
Synthesis of 2-methyl-4-selenoquinazolone, 2-phenylbenzoselenazole, and its derivatives: Dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Faculty of Pure Science of Columbia University
Chen, Yü-Gwan
Organic compounds -- Synthesis; Selenium; Thesis (Ph. D.)
Duhamel and Rebiere(6)(7) showed that an injection of a trace of red
colloidal selenium into rabbits increased urea excretion regularly. In
other cases satisfactory results were claimed and the liver showed some
lesions. The histological modifications produced by injections into
rabbits are most apparent in the liver and kidneys. In the distribution
of colloidal preparations in the animal body by injection, Duhamel and
Juillard(8) found that the liver contained the greatest amount. Six
years later the former(9) used a similar preparation introduced into
the animal intravenously, and selenium was again found in the liver,
although in smaller quantity.
Sulphur compounds have similar physiological action. It is known that
triphenylstibine sulphide, or sulphoform, (C₆H₅)₃SbS, has a curative
effect in skin diseases, as it liberates “nascent” sulphur on the
skin. It is equally natural to expect some organic selenium compound
which liberates finely divided selenium to exert a remedial influence
on animal bodies. The selenoquinazolone prepared in the course of this
research and described more fully in another section of the paper, has
this prospect. The quinazolone has the following structure:
N
/\ / \\
| | C-CH₃
| | |
| | NH
\/ \ /
C
Se
Experiments were carried on at L’Institut Pasteur in Paris under the
supervision of M. Borel for the treatment of cancer in mice. No human
subjects were experimented upon, although results were claimed by using
selenides and their oxidized salts.
Selenium dyes were found to be medicinals, although no relation has yet
been established between constitution of these organic dyes and their
therapeutic value. Wassermann(10) made several eosin preparations,
by coupling the sodium derivative with potassium selenocyanide. The
red dyestuff thus prepared is stated to be easily soluble in water.
Wassermann, Keysser and Wassermann(11) made experiments with it,
chemotherapeutically, on animal tumors. When the solution was injected
into mice tumors the latter turned red, accompanied by the softening
of the tumor after the third injection and complete resorption after
ten injections, unless the dose used was too great for the animal. In
that case death often occurred. Good results were also reported, in
connection with this experiment, on four different strains of mouse
carcinoma and one strain of mouse sarcoma. In the latter case, relief
was found sooner but the former disappeared more slowly. Another
preparation was made later(12) and introduced into mice intravenously
and again found to have good results.
The following is the structure of 2-selenocyanideanthraquinone--
O
C SeCN
/\ / \ /\ /
| | | |
| | | |
\/ \ / \/
C
O
which has also been reported to have medicinal uses(13).
P. Ehrlich and Hugo Bauer(14) synthesized from p.p′-diamino-diphenyl-
methane the red dye 3,6-diaminoselenopyronine.
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