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Synthesis of Sterically Rigid Cystamine Derivatives.
Final rept. 1 Jun 69-31 Aug 71,
CINCINNATI UNIV OHIO
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The possibility exists that the cystamine class of radiation protection drugs may be active only in certain conformations. If this should prove to be the case then cystamine derivatives that are rigidly held in the required conformation may be much more effective radiation protection agents than the freely rotating cystamine. This investigation has been directed toward the synthesis of bicyclic disulfides that can be converted into cystamine derivatives. One approach was directed towards the syntheses of the syn and anti isomers of 8-amino-2,3-dithiabicyclo3.2.1octane. A single isomer of 2,3-dithiabicyclo3.2.1octan-8-ol was prepared. A potential precursor for the anti isomer has been obtained in the form of trans-2,trans-6-dithioacetylcyclohex-r-l-yl acetate. The preparations of the p-toluenesulfonate and trifluoromethanesulfonate esters of syn-2,3-dithiabicyclo3.2.1octan-8-0l are described.
APPROVED FOR PUBLIC RELEASE