Synthesis and reactions of polyhedral compounds. 29. Synthesis and antibacterial activity of 1,3-diazaadamantane derivatives

Abstract

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.

Antibacterial Activity Exerted by some Diazabicyclo-steroid Derivatives Against Staphylococcus Aureus and Streptococcus Pneumoniae

“…There are reports which indicate the preparation of diazahicyclo derivatives as antibacterial agents; nevertheless, expensive reagents and special conditions are required [9][10][11][12][13][14][15][16][17] . Therefore, in this study three diazahicyclo-steroid derivatives were synthetized using several strategies to evaluate the biological activity against Staphylococcus aureus and Streptococcus pneumoniae.…”

“…Also, other report showed the preparation of 1,4-diazabicyclo-[2.2.2]octane with antibacterial activity against a Staphylococcus aureus strain 13 . Additionaly, other report shown that the diazabycycle derivative (1,3-diazaadamante) exerted antibacterial activity against Staphylococcus aureus 14 .…”

Theoretical Study on Molecular Structure and Electronic Properties of New 1,3-Diaza-adamantan-6-ones Derivatives

“…It consists of a polycyclic cage molecule with high symmetry representing diamondoids-hydrogen-terminated hydrocarbons with a diamond-like structure [7][8]. Among these derivatives, 1,3-Diaza-adamantane derivatives have attracted great attention due to their interesting properties [9] such as antibacterial, and psychotropic activity [10][11]. Sharabi-Ronen et al have reported the anti-neoplastic activity of 1,3-Diaza-2-functionalized-adamantan-6-one compounds against melanoma cells [12].…”

Synthesis of fragrant 1,3-diazaadamantan-6-ones

“…A renewed interest in chemistry of 1,3 diazaadaman tane (1,3 diazatricyclo[3.3.1.1 3,7 ]decane) 1 is explained not only by the presence of various physiological activity in its derivatives, 2-6 but also by the recent discovery of three alkaloids acosmine (1), acosmine acetate (2), and pana cosmine (3) with the structure of 1,3 diazaadamantane. 7 1,3 Diazaadamantan 6 ones are the most available de rivatives of 1,3 diazaadamantane, which are obtained by the condensation of hexamethylenetetramine with ketones of the formula RCH 2 COCH 2 R´ (Scheme 1).…”