The antibacterial activity of 1,3-diazaadamantane derivatives was studied; a degree of relationship between chemical structure and the antibacterial activity of the compounds synthesized was identified. The results obtained here showed that some of the study compounds were active against Gram-positive and Gram-negative microorganisms. 180091-150X/08/4201-0018 XVIII 4.65 s (1H, NCHN), 3.48 d (1H, J 5.4, OCH), 3.30 dd (1H, J 1 12.8, J 2 2.6, CH 2 N), 3.03 dd (1H, J 1 13.1, J 2 2.1, CH 2 N), 2.98 dd (1H, J 1 13.1, J 2 2.6, CH 2 N), 2.87 dd (1H, J 1 13.0, J 2 2.0, CH 2 N), 2.77 dd (1H, J 1 13.2, J 2 3.0, CH 2 N), 2.71 dd (1H, J 1 12.8, J 2 1.3, CH 2 N), 2.53 -2.45 m (2H, CH 2 N). 7.01 d (1H, J 1.0, 2'-H), 6.99 d (1H, J 1.0, 6¢-H), 6.70 d (1H, J 7.9, 5¢-H), 5.92 s (2H, OCH 2 O), 4.24 d (1H, J 5.4, OH), 1.31 dq (1H, J 1 13.8, J 2 7.5, CH 2 ), 1.00 -1.21 m (2H, CH 2 ), 0.73 m (1H, CH 2 ), 0.83 t (3H, J 7.5, CH 3 ), 0.65 t (3H, J 7.2, CH 3 ). XIX 4.74 s (1H, NCHN), 3.48 dt (1H, J 1 5.4, J 2 1.4, OCH), 3.23 dd (1H, J 1 12.8, J 2 2.9, CH 2 N), 2.99 dd (1H, J 1 13.0, J 2 2.4, CH 2 N), 2.93 dd (1H, J 1 13.0, J 2 2.4, CH 2 N), 2.90 dd (1H, J 1 13.0, J 2 2.9, CH 2 N), 2.84 dd (1H, J 1 13.0, J 2 3.1, CH 2 N), 2.68 dt (1H, J 1 12.9, J 2 1.6, CH 2 N), 2.61 dt (1H, J 1 13.1, J 2 1.6, CH 2 N), 2.54 dd (1H, J 1 13.2, J 2 3.2, CH 2 N). 7.36 d (1H, J 1.7, 5¢-H), 6.32 dd (1H, J 1 3.2, J 2 1.7, 4¢-H), 6.21 d (1H, J 3.2, 3¢-H), 4.33 d (1H, J 5.4, OH), 1.30 dq (1H, J 1 13.8, J 2 7.6, CH 2 ), 1.18 dq (1H, J 1 13.8, J 2 7.3, CH 2 ), 1.04 dq (1H, J 1 13.8, J 2 7.3, CH 2 ), 0.83 dq (1H, J 1 13.8, J 2 7.6, CH 2 ), 0.82 t (3H, J 7.6, CH 3 ), 0.68 t (3H, J 7.3, CH 3 ). XX 5.03 s (1H, NCHN), 3.54 d (1H, J 5.4, OCH), 3.34 dd (1H, J 1 12.8, J 2 3.1, CH 2 N), 3.15 dd (1H, J 1 13.0, J 2 2.3, CH 2 N), 3.02 dd (1H, J 1 13.0, J 2 3.1, CH 2 N), 2.98 dd (1H, J 1 13.1, J 2 2.2, CH 2 N), 2.90 -2.81 m (2H, CH 2 N), 2.69 dt (1H, J 1 12.8, J 2 1.4, CH 2 N), 2.58 dd (1H, J1 13.0, J 2 3.1, CH 2 N). 10.27 br s (1H, NH), 7.88 d (1H, J 8.1, 7¢-H), 7.12 d (1H, J 7.9, 4¢-H), 6.85 ddd (1H, J 1 7.8, J 2 7.1, J 3 1.3, 6¢-H), 6.75 ddd (1H, J 1 8.1, J 2 7.1, J 3 1.3, 5¢-H), 4.12 d (1H, J 5.4, OH), 2.46 s (3H, 2¢-CH 3 ), 1.31 dq (1H, J 1 13.9, J 2 7.5, CH 2 ), 1.23 -1.03 m (2H, CH 2 ), 0.68 m (1H, CH 2 ), 0.85 t (3H, J 7.5, CH 3 ), 0.65 t (3H, J 7.5, CH 3 ).* Prime marks identify protons of aromatic groups at position 2 of the 1,3-diazaadamantane nucleus.

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A number of new 1,3-diazaadamantane derivatives containing quinoline fragments on C 2 have been synthesized by condensation of 1,5-dialkyl-3,7-diazabicyclo[3.3.1]nonan-9-one, 1,5-dimethyl-3,7-diazabicyclo-[3.3.1]nonan-9-ol, and 1,5-dimethyl-3,7-diazabicyclo[3.3.1]nonane with 2-oxo-1,2-dihydroquinoline-3-carbaldehyde, 2-chloro-and 2-iodoquinoline-3-carbaldehyde, and quinoline-2-carbaldehyde.