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

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

European Pharmaceutical Journal

Volume 70 (2023): Issue 2 (December 2023)

By: R. Čižmáriková, L. Habala, J. Valentová, A. Némethy, K Bruchatá and K. Hroboňová

Open Access

|Sep 2023

Figures & Tables

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

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

HPLC chromatograms for enantioseparation of the compounds I (a) and VII (b) 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.

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
Propranolol^a	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

DOI: https://doi.org/10.2478/afpuc-2023-0015 | Journal eISSN: 2453-6725

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Language: English

Page range: 20 - 30

Submitted on: Aug 5, 2022

Accepted on: Aug 6, 2023

Published on: Sep 13, 2023

Published by: Comenius University in Bratislava, Faculty of Pharmacy

In partnership with: Paradigm Publishing Services

Publication frequency: 2 issues per year

Keywords:

β-sympatolytiká,

aryloxyaminopropanoly,

antiradikálová aktivita,

HPLC-enantioseparácia

Related subjects:

Pharmacy, other

© 2023 R. Čižmáriková, L. Habala, J. Valentová, A. Némethy, K Bruchatá, K. Hroboňová, published by Comenius University in Bratislava, Faculty of Pharmacy
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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