86579-60-4Relevant academic research and scientific papers
Spermicidal, anti-HIV, and micellar properties of di- and trihydroxylated cationic surfactants
Wong, Yue-Ling,Curfman, Christopher L,Doncel, Gustavo F,Patricia Hubieki,Dudding, Travis C,Savle, Prashant S,Gandour, Richard D
, p. 45 - 54 (2002)
The syntheses of 2-hydroxy-N-(2-hydroxyethyl)-N,N-dimethyl-1-alkanaminium 1(p) and 2-hydroxy-N,N-bis(2-hydroxyethyl)-N-methyl-1-alkanaminium 2(p) bromides are described for the homologous series, tetradecanaminium (p=14) through octadecaminium (p=18). The critical micelle concentrations (cmc's), measured by conductivity at 25 and 37°C, of the even-numbered members of the series show the expected linear dependence on chain length. All compounds display spermicidal and virucidal activity. Plots of minimum effective concentration (MEC) versus chain length in the Sander-Cramer spermicidal assay of 1 and 2 show a cut-off effect and a parabolic relationship, respectively. The best compounds - 1(17) and 1(18) - have MECs (～0.12mg mL-1) slightly lower than that of the commercial spermicide nonoxynol-9 (N-9). Compounds 1(16) and 2(17) show the best anti-HIV activity in in-vitro, cell-free and cell-associated virus inactivation assays. Both are highly effective at 0.1mg mL-1 in the cell-free assay and 0.5mg mL-1 in the cell-associated assay. Compound 1(16) shows the best combination of dual activity against sperm and HIV. In summary, hydroxylated cationic surfactants, 1 and 2, show promise as inexpensive topical, contraceptive microbicides.
Micellar Catalysis of Organic Reactions. 27. Micellar Bound Meisenheimer Complexes
Broxton, Trevor J.,Chung Roland P.-T.
, p. 3886 - 3890 (2007/10/02)
Reactions of nitro activated aryl halides with base in the presence of dihydroxy micelles of cetyl(2,3-dihydroxypropyl)dimethylammonium bromide (CDHPDAB) give rise to spiro Meisenheimer complexes that are covalently bound to the micelles.From the large fluorine/chlorine rate ratios observed for these reactions, we conclude that the initial attack on the aryl halide by the micellar hydroxyl group is the rate-determining step for the formation of the Meisenheimer complex.For the subsequent decomposition of the complex the rate of reaction is dependent on hydroxide concentration if the complex contains only one ortho substituent.This indicates that the breakdown of the aryl micellar ether formed in the first step of the decomposition is the rate-determining step.However, for complexes containing two ortho substituents, the rate of decomposition is almost independent of the hydroxide concentration, indicating for these complexes that the rate-determining step is the initial unimolecular breakdown of the Meisenheimer complex to form the micellar ether.It is proposed that this change is caused by the built-in solvation effect of Bunnett et al. in which the positive charge on the side chain of the complex is stabilized by an electrostatic interaction with either the negatively charged carboxylate group or the dipolar nitro group.
