760-21-4Relevant articles and documents
Vibrational and electronic circular dichroism studies on the axially chiral pyridine-N-oxide: trans-2,6-di-ortho-tolyl-3,4,5-trimethylpyridine-N-oxide
Teodorescu, Florina,Nica, Simona,Uncuta, Cornelia,Bartha, Emeric,Filip, Petru Ivan,Vanthuyne, Nicolas,Roussel, Christian,Mándi, Attila,Tóth, László,Kurtán, Tibor,Naubron, Jean-Valère,Man, Isabela-Costinela
, p. 1043 - 1049 (2015)
The absolute configuration of the resolved axially chiral pyridine-N-oxide derivative, (±)-trans-2,6-di-ortho-tolyl-3,4,5-trimethylpyridine-N-oxide, has been determined by VCD and ECD analyses supported by TD-DFT calculations carried out at different levels of theory. DFT calculations confirmed that in spite of the two biaryl axes, the compound is conformationally less flexible and the major conformer is stabilized by two weak hydrogen bonds formed between the hydrogen of the methyl group of the tolyl moieties and the nitroxide oxygen. The experimental VCD spectra of this compound and the previously studied (±)-2,6-di-sec-butyl-4-methylpyridine-N-oxide with two stereogenic centers were compared in the frequency range 1200-1300 cm-1. A (+,-,+)/(-,+,-) pattern of bands was observed in both cases. By replacing the sec-butyl moieties with tolyl ones, the VCD peaks shifted toward higher frequencies and the intensities were increased.
Original antileishmanial hits: Variations around amidoximes
Tabélé, Clémence,Fai?es, Viviane dos S.,Grimaud, Fabien,Torres-Santos, Eduardo Caio,Khoumeri, Omar,Curti, Christophe,Vanelle, Patrice
, p. 154 - 164 (2018/02/20)
In continuation to our previous findings on amidoximes' antiparasitic activities, a new series of 23 original derivatives was designed and obtained by convergent synthesis. First, new terminal alkenes were synthesized by cross-coupling reaction. Then, cyclization was performed between terminal alkenes and β-ketosulfones using manganese(III) acetate reactivity. Twenty-three amidoximes were tested for their in vitro activity against Leishmania amazonensis promastigotes and their toxicity on murine macrophages. Seven of the tested compounds exhibited an antileishmanial activity at lower than 10 μM with moderate to low toxicity. Six of these molecules showed activity at lower than 10 μM against promastigotes and toxicity at higher than 50 μM were selected and evaluated for their activity against intracellular Leishmania amazonensis amastigotes. Modulating chemical substituents in position 2 of dihydrofuran highly influenced their antileishmanial activities. The introduction of a methyl or trifluoromethyl group on the benzene ring of the benzyl group had a positive influence on activity without significantly increasing toxicity (52, 59, 60).
DIARYL AMINE ANTIOXIDANTS PREPARED FROM BRANCHED OLEFINS
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Paragraph 0058; 0059, (2017/02/09)
Diaryl amines are selectively alkylated by reaction with branched olefins, which olefins are capable of forming tertiary carbonium ions and can be conveniently prepared from readily available branched alcohols. The diaryl amine products are effective antioxidants and often comprise a high amount of di-alkylated diaryl amines and a low amount of tri- and tetra-alkylated diaryl amines.
