Azacycloalkanes. XXVII. Synthesis and antianginal activity of nonachlazine stereoisomers

The preparation nonachlazine, which is the dihydrochloride of 10-[~-N-(l,4-diazabicyclo [4.3.0]nonanyl)propionyl]-2-chlorophenothiazine (I), was synthesized in the Institute of Pharmacology of the Academy of Medical Sciences of the USSR (AMN SSSR) and is used in medical practice as an antianginal agent [2, 3]. The diazabicyclic fragment of nonachlazine contains an asymmetric carbon atom as a result of which nonachlazine may exist as two optical antipodes. The present work is devoted to the synthesis of these optical antipodes, the establishment of their absolute configuration, and also the clarification of certain problems of the relationship between chemical structure and antianginal activity in a series of N-aminoacyl derivatives of phenothiazine.