Synthesis of 2-thia-4-azabicyclo[3.3.1]non-3-en-3-amine – bridged nitric oxide synthase inhibitor with enhanced lipophilicity

2-Thia-4-azabicyclo[3.3.1]non-3-en-3-amine was synthesized as a lipophilic analogue of NO-synthase inhibitor 2-amino-5,6-dihydro- 4 H -1,3-thiazine and found to be a potent inhibitor of inducible NO-synthase in vitro . The crystal structure of the key intermediate 2-thia-4-azabicyclo[3.3.1]nonane-3-thione (obtained by cyclization of trans -3-bromocyclohexylamine with carbon disulfide) was determined by X-ray analysis.