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Synthesis, antioxidant activity, and HPLC enantioseparation of aryloxyaminopropanols derived from naphthalen-2-ol

R. Čižmáriková
R. Čižmáriková
, 
L. Habala
L. Habala
, 
J. Valentová
J. Valentová
, 
A. Némethy
A. Némethy
, 
K Bruchatá
K Bruchatá
 und 
K. Hroboňová
K. Hroboňová
   | 13. Sept. 2023
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Article Category: Original Paper
Online veröffentlicht: 13. Sept. 2023
Seitenbereich: 20 - 30
Eingereicht: 05. Aug. 2022
Akzeptiert: 06. Aug. 2023
DOI: https://doi.org/10.2478/afpuc-2023-0015
Schlüsselwörter
© 2023 R. Čižmáriková et al., published by Sciendo
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Scheme 1.

Synthesis of 2-[(naphthalen-2-yloxy)methyl]oxirane.
Synthesis of 2-[(naphthalen-2-yloxy)methyl]oxirane.

Scheme 2.

Synthesis of (2RS)-1-(2-naphthyloxy)-3-(substituted amino)propan-2-ols.
Synthesis of (2RS)-1-(2-naphthyloxy)-3-(substituted amino)propan-2-ols.

Figure 1.

HPLC chromatograms for enantioseparation of the compounds I (a) and VII (b) on Chiralpak AD-H column with the mobile phase B.
HPLC chromatograms for enantioseparation of the compounds I (a) and VII (b) on Chiralpak AD-H column with the mobile phase B.

Figure 2.

HPLC chromatogram for enantioseparation of the compound VIa on Chiralpak AD-H column with the mobile phase B.
HPLC chromatogram for enantioseparation of the compound VIa on Chiralpak AD-H column with the mobile phase B.

Figure 3.

HPLC chromatogram for enantioseparation of the compound VIIIa on Chiralpak AD-H column with the mobile phase D.
HPLC chromatogram for enantioseparation of the compound VIIIa on Chiralpak AD-H column with the mobile phase D.

Screening of antioxidant activities of salts and free bases of the prepared compounds.

Compound Working label Inhibition of ABTS (%) ± SD
I B2N IZP 90.90 ±1.90
Ib H2NIZP 31.66 ±2.73
II B2N4t 81.97 ±1.94
IIa F2N4t 9.33 ±3.77
IIIa F2NDMA 8.12 ±3.20
IVa F2N-CH 33.51 ±3.30
VIIa F2N pyrr 11.71 ±0.64
VIIb H2N pyrr 21.99 ± 0.81
VIII B2N-IMI 52.18 ±1.5
IX B2N-2IMI 57.10 ±6.60
Xa F2Npiper 6.01 ±1.09
XIa F2Nmorph 17.76 ±0.94
XII B2NCH3piper 92.92 ±1.16
XIIIa F2NMFP 41.71 ±9.50
XVI Imidazole Inactive
XVII 2-methylimidazole 5.42 ±1.30
XIV Naphthalen-1-ol 99.64 ±0.16
XV Naphthalen-2-ol 99.63 ±0.30
Propranolola Standard 97.48 ± 2.34

Chromatographic parameters of the derivatives of 2-naphthol on the chiral column Chiralpak AD-H.

Compound Mobile phase t1 t2 k1 k2 α Rs
I B 7.88 13.83 1.11 2.71 2.44 14.88
III B 10.41 12.90 1.70 2.35 1.38 4.15
IVa A 12.26 21.14 1.97 4.13 2.09 12.96
IVa B 10.44 17.77 1.69 3.58 2.12 12.01
V A 49.08 84.03 11.37 20.17 1.77 12.83
V B 37.82 64.31 8.49 15.13 1.78 12.32
VIa B 29.48 65.29 6.59 15.82 2.40 14.32
VII B 11.20 12.91 1.33 1.69 3.85 1.27
VIIIa D 17.72 20.87 4.54 5.52 0.82 3.50
VIIIa B 27.97 33.75 6.32 7.83 1.24 4.21
IX B 56.58 -- - - - -
IX D 41.44 - - - - -
XII B 13.45 18.05 2.60 3.80 6.35 1.46
XIIIa B 8.55 - - - - -
XIIIa C 7.75 - - - - -
XIIIa A 9.75 - - - - -

Chromatographic parameters of the derivatives of 2-naphthol on the chiral column Chirobiotic T.

Compound Mobile phase t1 t2 k1 k2 α Rs
III E 15.20 15.60 3.93 4.06 1.03 0.77
IV E 15.98 17.04 3.32 3.61 1.09 1.18
V E 3.18 - - - - -
VI E 17.53 19.80 3.74 4.36 1.17 2.67

List of the studied compounds.

Compound R Compound R
I -NHCH(CH3)2 X
II -NHC(CH3)3 XI
III -N(CH3)2 XII
IV XIII
V XIV
VI XV
VII XVI
VIII XVII
IX
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