Polycations. 18. The synthesis of polycationic lipid materials based on the diamine 1,4-diazabicyclo[2.2.2]octane

Third-generation ionic liquids with N-alkylated 1,4-diazabicyclo[2.2.2]octane cations and pelargonate anions

“…The obtained product was dried for 24 h in a vacuum oven at 60 C. The rst step was the quaternization of bicyclic tertiary diamine (DABCO), which allowed preparing the 1-alkyl-1azonia-4-azabicyclo[2.2.2]octane bromides according to the described methodology. 42 The synthesized monoalkyl bromides, precursors of the ILs, were characterized in an earlier report, in which the physicochemistry of the compounds and their antimicrobial properties were presented. 33 In the second step, the bromide anions were replaced with hydroxide anions in the exchange reaction.…”

Synthesis and structure–activity relationship of novel 1,4-diazabicyclo[2.2.2]octane derivatives as potent antimicrobial agents

“…1 H NMR (DMSO-d 6 , 400 MHz): δ = 0.86 (br.t., 6H, CH 3 (CH 2 ) 17 N + ); 1.25 (m, 60H, CH 3 (CH 2 ) 15 (CH 2 ) 2 N + ); 1.40 (m, 2H, + N(CH 2 ) 2 CH 2 (CH 2 ) 2 N + ); 1.72 (m, 4H, CH 3 (CH 2 ) 15 CH 2 CH 2 N + ); 1.85 (m, 4H, + NCH 2 CH 2 CH 2 CH 2 CH 2 N + ); 3.54 (m, 4H, CH 3 (CH 2 ) 16 CH 2 N + ); 3.67 (m, 4H, + NCH 2 (CH 2 ) 3 CH 2 N + ); 3.95-3.99 (m, 24H, + N(CH 2 CH 2 ) 3 N + ). 13 C NMR (DMSO-d 6 , 100 MHz): δ = 14.33 (CH 3 (CH 2 ) 17 N + ); 21.32 ( + NCH 2 CH 2 CH 2 CH 2 CH 2 N + ); 21.82 (CH 3 (CH 2 ) 15 CH 2 CH 2 N + ); 22.49 (CH 3 (CH 2 ) 14 CH 2 (CH 2 ) 2 N + ); 22.88 ( + N(CH 2 ) 2 CH 2 (CH 2 ) 2 N + ); 26.04 (CH 3 (CH 2 ) 13 CH 2 (CH 2 ) 3 N + ); 28.89 (CH 3 (CH 2 ) 12 CH 2 (CH 2 ) 4 N + ); 29.09 (CH 3 (CH 2 ) 11 CH 2 (CH 2 ) 5 N + ); 29.20 (CH 3 (CH 2 ) 10 CH 2 (CH 2 ) 6 N + ); 29.46 (CH 3 (CH 2 ) 9 CH 2 (CH 2 ) 7 N + , CH 3 (CH 2 ) 8 CH 2 (CH 2 ) 8 N + , CH 3 (CH 2 ) 7 CH 2 (CH 2 ) 9 N + , CH 3 (CH 2 ) 6 CH 2 (CH 2 ) 10 N + , CH 3 (CH 2 ) 5 CH 2 (CH 2 ) 11 N + , CH 3 (CH 2 ) 4 CH 2 (CH 2 ) 12 N + , CH 3 (CH 2 ) 3 CH 2 (CH 2 ) 13 N + , CH 3 (CH 2 ) 2 CH 2 (CH 2 ) 14 N + , CH 3 CH 2 CH 2 (CH 2 ) 15 N + ); 31.71 (CH 3 CH 2 (CH 2 ) 16 N + ); 50.94 and 51.04 ( + N(CH 2 CH 2 ) 3 N + ); 63.52 (CH 3 (CH 2 ) 16 CH 2 N + ); 64.08 ( + NCH 2 (CH 2 ) 3 CH 2 N + ). Anal.…”

“…13 400 MHz): δ = 0.85 (br.t., 6H, CH 3 (CH 2 ) 8 N + ); 1.27-1.34 (m, 26H, CH 3 (CH 2 ) 6 (CH 2 ) 2 N + , + N(CH 2 ) 2 CH 2 (CH 2 ) 2 N + ); 1.70 (m, 4H, CH 3 (CH 2 ) 6 CH 2 CH 2 N + ); 1.82 (m, 4H, + NCH 2 CH 2 CH 2 CH 2 CH 2 N + ); 3.56 (m, 4H, CH 3 (CH 2 ) 7 CH 2 N + ); 3.67 (m, 4H, + NCH 2 (CH 2 ) 3 CH 2 N + ); 3.96-3.99 (m, 24H, + N(CH 2 CH 2 ) 3 N + ). 13 C NMR (DMSO-d 6 , 100 MHz): δ = 13.96 (CH 3 (CH 2 ) 8 N + ); 20.79 ( + NCH 2 CH 2 CH 2 CH 2 CH 2 N + ); 21.30 (CH 3 (CH 2 ) 6 CH 2 CH 2 N + ); 22.08 (CH 3 (CH 2 ) 5 CH 2 (CH 2 ) 2 N + ); 22.28 ( + N(CH 2 ) 2 CH 2 (CH 2 ) 2 N + ); 25.50 (CH 3 (CH 2 ) 4 CH 2 (CH 2 ) 3 N + ); 28.42 (CH 3 (CH 2 ) 3 CH 2 (CH 2 ) 4 N + ); 28.56 (CH 3 (CH 2 ) 2 CH 2 (CH 2 ) 5 N + );…”

“…Recently, the variety of QACs based on 1,4-diazabicyclo[2.2.2]octane (DABCO) such as mono-and dialkylated DABCO derivatives, polycationic glycosides, DABCO units covalently attached to wool and silk surfaces were synthesized and evaluated against a series of bacteria [19][20][21][22]. Antibacterial and antifungal activities have been noted for the incorporation of lipid chains of 12 and 16 carbons directly attached to nitrogen of a DABCO unit [15].…”

Polycations XXII. Ru(bpy)2L2 and Ru(phen)2L2 Systems with Cationic 4,4’-Bipyridine Ligands: Syntheses, Characteristics, and Interactions with DNA

“…As has been noted in prior investigations, the use of ethyl acetate as a medium for the quaternization facilitates immediate precipitation of the mono-alkylated species, thereby preventing additional alkylation. [4] Syntheses, spectrophotometric, and analytical data for the newly synthesized cationic ligands are exhibited in Table 1. All materials prepared are mildly hydroscopic but can be rendered anhydrous readily under high vacuum at ambient temperature.…”