THE SYNTHESIS OF BETA-MERCAPTOETHYLAMINES OF VARYING BASICITY AND LIPOSOLUBILITY.
Final rept., June 59-Aug 63,
MASSACHUSETTS COLL OF PHARMACY BOSTON
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Derivatives of 2-mercaptoethylamine MEA and 2mercaptoethylguanidine MEG have been synthesized to provide radioprotective compounds of lower toxicity than MEA and MEG and which exhibit a fairly wide range of liposolubility. The derivatives have included acyl thioesters, where the acyl groups are derived from straight chain aliphatic acids and alpha-amino acids, as well as straight chain N-alkyl derivatives of chain length up to fourteen carbons. These derivatives were generally less toxic than the parent compounds, and in several of them good radioprotective activity was retained. Trithiocarbonates of MEA and MEG and some of their derivatives have been prepared and found to have good antiradiation properties. The toxicity of MEA trithiocarbonate is significantly less than that of MEA. Di- or trisubstitution of the nitrogens resulted in reduced activity. Dithiocarbamates of a number of amines and diamines gave radioprotection of a lower order than provided by the mercaptan bases. Other compounds synthesized where little or no activity has been found include mercaptoethyl and dithiocarbamate derivatives of strongly basic heterocycles, and derivatives of mercaptobiacetyl and bithiourea. Author