Accession Number:

ADA002587

Title:

Synthesis of Sterically Rigid Cystamine Derivatives.

Descriptive Note:

Final rept. 1 Jun 69-31 Aug 71,

Corporate Author:

CINCINNATI UNIV OHIO

Personal Author(s):

• Wilson,R. Marshall
• Buchanan,Douglas N.

Report Date:

1974-07-01

Pagination or Media Count:

29.0

Abstract:

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.

Descriptors:

• *STEREOCHEMISTRY
• *POLYCYCLIC COMPOUNDS
• *RADIOPROTECTIVE AGENTS
• NUCLEAR MAGNETIC RESONANCE
• SYNTHESIS(CHEMISTRY)
• AMINES
• MOLECULAR STRUCTURE
• MOLECULAR ISOMERISM
• SULFIDES
• INFRARED SPECTRA
• HETEROCYCLIC COMPOUNDS
• ORGANIC SULFUR COMPOUNDS

Subject Categories:

• Radiobiology
• Organic Chemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE