Synthesis of Potential Anti-Vesicant Compounds.
Annual rept. 19 Dec 90-31 Dec 91,
ASH STEVENS INC DETROIT MI
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Four classes of compounds have been proposed to inactivate sulfur mustard. Each class is comprised of a carrier molecule type containing a bis thiol which is capable of forming a five or six membered cyclic disulfide. The carrier molecule also contains hydroxyl or amino groups proximal to the thiols which are proposed to enhance thiolate formation and aid in binding of the molecule to phospholipid membranes. The first class is cysteine derivatives. It was originally proposed to prepare cysteinamide and cysteinol derivatives containing n-alkyl side chains from C-6 to C-18 to vary the lipophilicity of the compounds. The cysteine derivative class contains three types of molecules. In order or priority they are 2-amino-1,3-propanedithiol derivatives, cysteinol derivatives, and cysteinamides. Each type is proposed to be prepared from an S- and N-protected cysteine starting material. The lipophilicity of emphasis on non hygroscopic crystalline compounds to facilitate their testing as antivesicants. Cystine compounds are also included since they are often more crystalline and the sulfur is protected as its disulfide.
- Organic Chemistry
- Chemical, Biological and Radiological Warfare