355-28-2Relevant articles and documents
Incorporation of a 3-(2,2,2-Trifluoroethyl)-γ-hydroxy-γ-lactam motif in the side chain of 4-aminoquinolines. Syntheses and antimalarial activities
Cornut, Damien,Lemoine, Hugues,Kanishchev, Oleksandr,Okada, Etsuji,Albrieux, Florian,Beavogui, Abdoul Habib,Bienvenu, Anne-Lise,Picot, Stéphane,Bouillon, Jean-Philippe,Médebielle, Maurice
, p. 73 - 83 (2013/02/23)
In this paper we report the synthesis and antimalarial properties of two series of fluoroalkylated γ-lactams derived from 4-aminoquinoline as potent chemotherapeutic agents for malaria treatment. These molecules obtained in several steps resulted in the identification of very potent structures with in vitro activity against Plasmodium falciparum clones of variable sensitivity (3D7 and W2) in the range of 19-50 nM with resistance indices in the range of 1.0-2.5. In addition, selected molecules (50, 51, 58, 60, 63, 70, 72, 74, 78, 81, 84, and 87) that are representative of the two series of compounds did not show cytotoxicity in vitro when tested against human umbilical vein endothelial cells up to a concentration of 100 μM. The most promising compounds (82 and 84) showed significant IC50 values close to 26 and 19 nM against the chloroquino-sensitive strain 3D7 and 49 and 42 nM against the multi-drug-resistant strain W2. Furthermore, two model compounds (50 and 70) were found to be quite stable over 48 h at pH 7.4 and 5.2. Overall, our preliminary data indicate that this class of structures contains promising candidates for further study.
Aggregation Behavior of Mixed Fluorocarbon and Hydrocarbon Molecules in Aqueous Organic Solvents. Nonideality and Ideality of Mixing
Tung, Chen-Ho,Ji, Hai-Feng
, p. 8311 - 8316 (2007/10/02)
The emission spectra of naphthalene labeled hydrocarbons (NpHCn) and fluorocarbons (NpFCn) and anthracene labeled hydrocarbons (AnHCn) and fluorocarbons (AnFCn) in aqueous organic mixed solvents were investigated.The fluorescence spectrum of NpHC16 in dimethyl sulfoxide-water (DMSO-H2O) is dominated by excimer emission due to formation of aggregates.Addition of a fluorocarbon compound with chain length of seven perfluoromethylenes results in a reduction in the excimer emission and an enhancement of monomer emission, suggesting formation of coaggregates.In contrast, addition of a perfluorocarbon compound with chain length of 12 perfluoromethylenes results in no change in the fluorescence spectrum of NpHC16.Similarly, NpFC7 and NpFC12 in DMSO-H2) also exhibit excimer emission exclusively.Fluorescence studies show that hydrocarbon compounds coaggregate with NpFC7 but do not coaggregate with NpFC12.Selective excitation of the naphthalene moiety in the mixture solution of NpHC16 with AnFC7 or in the mixture solution of NpFC7 with AnHC12 exclusively leads to the emission of the anthracene moiety, suggesting that efficient energy transfer between the naphthalene and the anthracene chromophores occurs.On the other hand, for the mixture of NpHC16 with AnFC12 or NpFC12 with AnHC12, no energy tranfer was detected.All these observations indicate that fluorcarbon compounds with short chains can mix with hydrocarbon compounds ideally, while those with long chains behave nonideally.The mixed critical aggregation concentrations of NpHC16 with NpFC7 and with NpFC12 are measured as a function of overall composition of the mixtures, which give insight into yje magnitude of the nonideality of the mixings.
