k 2021

Investigation of interactions of ortho- and para-N-aryl-substituted 2-trifluoromethylcinnamanilides

PINDJAKOVÁ, Dominika, Lucia VRÁBLOVÁ, Tomáš STRHÁRSKY, Jiří KOS, Josef JAMPÍLEK et. al.

Základní údaje

Originální název

Investigation of interactions of ortho- and para-N-aryl-substituted 2-trifluoromethylcinnamanilides

Autoři

PINDJAKOVÁ, Dominika, Lucia VRÁBLOVÁ, Tomáš STRHÁRSKY, Jiří KOS a Josef JAMPÍLEK

Vydání

The 25th International Electronic Conference on Synthetic Organic Chemistry, 2021

Další údaje

Jazyk

angličtina

Typ výsledku

Prezentace na konferencích

Obor

10400 1.4 Chemical sciences

Stát vydavatele

Švýcarsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

Organizační jednotka

Farmaceutická fakulta

Klíčová slova anglicky

N-arylcinnamamides; synthesis; lipophilicity determinations; structure-lipophilicity relationships

Příznaky

Mezinárodní význam, Recenzováno
Změněno: 14. 4. 2022 13:37, JUDr. Sabina Krejčiříková

Anotace

V originále

Unsubstituted (2E)-N-phenyl-3-[2-(trifluoromethyl)phenyl]prop-2-enamide and six other ortho- or para-halogen-substituted anilides of 2-(trifluoromethyl)cinnamic acid were prepared. As the benzene nucleus of cinnamic acid itself is substituted in C(2) position with a trifluoromethyl moiety that is spatially close to both the amide bond and the halogen (F, Cl, CF3) ortho-substitution of the anilide ring, interesting intramolecular interactions can be expected. Other derivatives are substituted at the para-position of the anilide ring, so that intermolecular interactions can be expected. Thus, it can be assumed that the predicted properties, especially lipophilicity, will differ significantly from the experimentally determined values. All the discussed compounds were analyzed using the reversed-phase high performance liquid chromatography method. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using an end-capped non-polar C18 stationary reversed-phase column. In the present study, the structure-lipophilicity relationships of the studied compounds are discussed.