Conformational state of β-hydroxynaphthylamides: Barriers for the rotation of the amide group around CN bond and dynamics of the morpholine ring

In vitro antifungal activity of organic compounds derived from amino alcohols against onychomycosis

“…Thus, the discovery of novel antifungal compounds is urgently necessary to develop more effective, economical therapies with fewer side effects. Amine and amide groups are significant functional groups in medications due to their reactive and chemical properties, 27 and these groups comprise peptides found in various proteins 28 . Our previous data show that amino alcohols have antimicrobial and immunological activities against Trypanosoma cruzi 29, 30, 31, 32.…”

Intramolecular Hydrogen Bonds in Selected Aromatic Compounds: Recent Developments

“…Therefore, a detailed description of the conformation of systems with the amide moiety is very important. In the papers [66][67][68][69], it was shown that salicylamides can form two types of hydrogen bonds-intramolecular in 5-chloro-2-hydroxy-benzamide and intermolecular in 2-hydroxy-N,N-diethylbenzamide in the solid state ( Figure 14). Studies of the IR, NMR (Nuclear Magnetic Resonance), and UV-Vis spectra, recorded as a function of temperature in non-polar, proton-accepting, and proton-donating solvents [68,69], prove the existence of an equilibrium between intramolecular and intermolecular hydrogen bonds.…”

“…In the papers [66][67][68][69], it was shown that salicylamides can form two types of hydrogen bonds-intramolecular in 5-chloro-2-hydroxy-benzamide and intermolecular in 2-hydroxy-N,N-diethylbenzamide in the solid state ( Figure 14). Studies of the IR, NMR (Nuclear Magnetic Resonance), and UV-Vis spectra, recorded as a function of temperature in non-polar, proton-accepting, and proton-donating solvents [68,69], prove the existence of an equilibrium between intramolecular and intermolecular hydrogen bonds. It is noteworthy that the ease of breaking the strong intramolecular hydrogen bond (e.g., for 4-chloro-2-hydroxybenzamide d(O … O) = 2.526 Å) in 2-hydroxy-N,N-diethylbenzamide is the result of a strong steric effect of ethyl groups and weakened π-electronic coupling between the phenyl and amide fragments [67].…”

“…In Ref. [68], the equilibrium between the intermolecular and intramolecular hydrogen bonds, as well as the rotation of the dimethylamine, morpholine, or pyrrolidine groups, were analysed. In Ref.…”

“…In Ref. [68], the 1 H and 13 C NMR spectra of 2-hydroxy-N,N-diethylbenzamide, measured as a function of temperature and solvent polarity, showed the existence of a dynamic effect resulting from the orientation of ethyl groups. On the basis of the temperature-dependent 1 H and 13 C NMR spectra ( Figure 15) and DFT calculations, it was found that the intramolecular hydrogen bond can be observed in aprotic solvents for β-hydroxy naphthalene amides, whereas, in protic solvents (based Studies of the IR, NMR (Nuclear Magnetic Resonance), and UV-Vis spectra, recorded as a function of temperature in non-polar, proton-accepting, and proton-donating solvents [68,69], prove the existence of an equilibrium between intramolecular and intermolecular hydrogen bonds.…”