Surface Active Properties of Simple Cyclic and Heterocyclic Amines in Water.

Abstract

The surface tension of aqueous solutions of simple cyclic, heterocyclic and aromatic amines was measured with a Du Nöuy tensiometer at 25 degrees C and the results discussed in terms of structure-aggregation relationships. The simple compounds used in this study were piperazine, piperidine, morpholine, 3-methylpyridine, cyclohexylamine and benzylamine, with carbon numbers ranging from four to seven. Piperazine, piperidine and morpholine did not form micellar associations but cyclohexylamine, benzylamine and 3-methylpyridine did, indicating that more than six carbons are necessary to form micellar associations, at least for compounds having a six-membered ring.

Tunable Methacrylamides for Covalent Ligand Directed Release Chemistry

“…The aniline 1c was the least reactive, with t 1/2 = 66 h. Finally, 1j , which only underwent addition without elimination of its primary alcohol, was very slow to react with t 1/2 ≥ 100 h. Counterintuitively, the substituted methacrylamides were more reactive than the unsubstituted acrylamide. We observed a clear correlation between the p K a of the leaving group (p K b in the case of amines) − and the t 1/2 of the model compounds’ reaction with GSH (Figure B). In these reactions with GSH, we found no decomposition of the compounds under the reaction conditions (within the duration of the assay; >12 h).…”

Vipirinin, a Coumarin-based HIV-1 Vpr Inhibitor, Interacts with a Hydrophobic Region of VPR

“…The potency of the methylpiperazine substitute (10), however, was similar to that of 3, most likely because of the low solubility of this compound (32). The higher potency of vipirinin, the morpholine analog, may be due, at least in part, to the aqueous miscibility associated with its morpholine moiety and to its higher surface activity compared with piperidine (38). Surface activity, although not solely responsible, corresponds to biological activity in many drugs (39).…”