- Design and evaluation of switchable-hydrophilicity solvents
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Switchable-hydrophilicity solvents (SHSs) are solvents that can switch reversibly between one form that is miscible with water to another that forms a biphasic mixture with water. For these SHSs, we use CO2 at 1 bar as a stimulus for triggering the transformation to the water-miscible form and removal of CO2 to achieve the reverse. We now report the identification of 13 new SHSs, including the first secondary amine SHSs, and a comparison of all known SHSs in terms of safety and environmental impacts. Amines which include another functional group, especially oxygen-containing groups, are less hazardous than alkylamines. Secondary amines can have improved switching speeds relative to tertiary amines. The variety of SHSs identified suggests that amine SHSs can be designed to have ideal properties for a given application.
- Vanderveen, Jesse R.,Durelle, Jeremy,Jessop, Philip G.
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- Carbon isosteres of the 4-aminopyridine substructure of chloroquine: Effects on pKa, hematin binding, inhibition of hemozoin formation, and parasite growth
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Unlike diprotic chloroquine (CQ), its two 4-aminoquinoline carbon isosteres (1, 2) are monoprotic at physiological pH. Compared to CQ, hematin binding affinity of 1 decreased 6.4-fold, and there was no measurable binding for 2. Although 1 was a weak inhibitor of hemozoin formation, neither isostere inhibited P. falciparum in vitro. Evidently, the CQ-hematin interaction is largely a function of its pyridine substructure, but inhibition of hemozoin formation and parasite growth depends on its 4-aminopyridine substructure.
- Cheruku, Srinivasa R.,Maiti, Souvik,Dorn, Arnulf,Scorneaux, Bernard,Bhattacharjee, Apurba K.,Ellis, William Y.,Vennerstrom, Jonathan L.
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- Process for the preparation of 4-amino-chloroquinolines
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4-Amino-chloroquinolines of the formula: STR1 in which R1 represents a hydrogen atom or an alkyl radical (1 to 5 carbon atoms), and R2 represents an alkyl radical (1 to 5 carbon atoms) optionally substituted by a dialkylamino group, or a phenyl radical optionally substituted by one or more carboxy and hydroxy radicals and alkyl radicals (1 to 4 carbon atoms) optionally substituted by a dialkylamino group, are prepared by the condensation of an amine of the formula: STR2 with a chloro-1,2,3,4-tetrahydroquinolin-4-one of the formula: STR3 with aromatization of the tetrahydroquinoline, the reaction being carried out in the presence of a ruthenium based catalyst on a support. The 4-amino-chloroquinoline products are useful as pharmaceuticals.
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