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.)
CH
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H₂N| | | |NH₂
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Se
The dye has been used upon mice and caused pronounced edema. The
toxicity of both the selenopyronine and the corresponding sulphur
compound was compared under similar conditions in the same experiment,
and it was found that the selenium dye was toxic in 1/3000 gram, but
the sulphur dye was toxic in 1/2500 gram per twenty gram weight of the
animal.
This physiological activity was noted years ago with the inorganic
compounds of selenium and Berzelius(15) described the poisonous effect
of hydrogen selenide quite impressively; “In order to get acquainted
with the smell of this gas I allowed a bubble not larger than a pea to
pass into my nostril; in consequence of its smell I so completely lost
my sense of smell for several hours that I could not distinguish the
odor of strong ammonia even when held under my nose. My sense of smell
returned after five or six hours, but severe irritation of the mucous
membrane set in and persisted for a fortnight.” The writer has been
working on the gas for some time and was also quite seriously affected
once, the injury persisting for many days. That it is more poisonous
than the hydrogen sulphide is well known.
Bruere(16) showed that when hydrogen sulphide was passed into blood
solution sulphemoglobin was produced in considerable quantity, due
to the chemical action of sulphur and hematin. He stated further
that sulphemoglobin may be found in animal blood when a large
amount of the gas has been inhaled. He made selenhemoglobin in the
same manner. Sixteen years later, Clarke and Hurtley also proved
that selenhemoglobin may be made by passing hydrogen selenide into
blood(17). These experiments may be interpreted to mean that the
oxy-hemoglobin is transformed into an organic complex of sulphur or
selenium, and that the transference may be more rapid and powerful in
the case of hydrogen selenide.
Biological investigations have sufficiently proved that dyestuffs of
the phenazine, oxazine, thiazine, acridine series show an injurious
effect on protozoa, especially those dyes containing substituted amino
groupings and of a simple structure(18). In the case of the thiazine
dyes of the methylene blue class, the physiological importance has well
recognized in their use as feeble antiseptics and analgesics. Ehrlich
and Guttmann(19) initiated the use of methylene blue as an antiperiodic
and its use in that line has been continued.
In the field of the selenazine dyes, pharmacologists have not yet paid
much attention to them, on account of the newness of the discovery, but
P. Karrer claims that they are indisputably “vital dyestuffs”(20). The
prospect of synthesizing selenazine dyes and their use as drugs seems
to be bright, judging from the fact that they are easily prepared and
capable of many combinations, especially of the ease with which they
form organic complexes with arsenic compounds.
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