Open Access

Synthesis, antimicrobial and antiradical activity of (3-alkoxymethyl-4-hydroxyphenyl)propan-1-ones, intermediates of biologically active compounds and activity comparison with 3-(alkoxymethyl)-4-(alkylamino-2-hydroxypropoxyphenyl)alkanones type of beta blockers

R. Čižmáriková
R. Čižmáriková
, 
M. Markuliak
M. Markuliak
, 
L. Habala
L. Habala
, 
J. Valentová
J. Valentová
 and 
A. Bilková
A. Bilková
   | Mar 11, 2021
European Pharmaceutical Journal's Cover Image
About this article
Previous Article
Next Article
Cite
Article Category: Original Paper
Published Online: Mar 11, 2021
Page range: 34 - 44
Received: Jan 23, 2021
DOI: https://doi.org/10.2478/afpuc-2020-0012
Keywords
© 2020 Čižmáriková R. et al., published by Sciendo
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Figure 1

Synthetic route for derivatives of propiophenone and chemical structures of derivatives of acetophenone.
Synthetic route for derivatives of propiophenone and chemical structures of derivatives of acetophenone.

Antimicrobial activity of (2RS)- bis [3-(4-propionyl-2-alkoxymethyl)phenoxy-2-hydroxypropyl]isopropylammonium fumarate.

Description R1 R2 MIC(mmol/L) E. coli MIC(mmol/L) S. aureus MIC(mmol/L) C. albicans
FpP4n3i CH3CH2 (CH2)3CH3 N 0.61 n
FpP5n3i CH3CH2 (CH2)4CH3 N 0.35 n
FpP6n3i CH3CH2 (CH2)5CH3 0.34 0.08 0.23
FpP7n3i CH3CH2 (CH2)6CH3 0.22 0.03 0.07
FpP9n3i CH3CH2 (CH2)8CH3 0.20 0.01 0.01
FpA5n3i CH3 (CH2)4CH3 N 0.61 n
FpA6n3i CH3 (CH2)5CH3 0.35 0.08 0.24
FpA7n3i CH3 (CH2)7CH3 0.23 0.07 0.23
FpA8n3i CH3 (CH2)7CH3 0.22 0.03 0.08
FpA9n3i CH3 (CH2)8CH3 0.21 0.01 0.02
ciprofloxacin 3.10−4 6.89.10−4 n

Antioxidative activity of (2RS)-bis [3-(4-acetyl-2-alkoxymethyl)phenoxy-2-hydroxypropyl]isopropylammonium fumarate exhibiting beta-blocking activity.

Description R1 R2 Inhibition DPPH [%]±SD Inhibition ABTS [%]±SD
FA23i CH3 CH2CH3 N 99.0±1.3
FA5n3i CH3 (CH2)4CH3 N 48.5±0.8
FA5i3i CH3 CH2CH2CH(CH3)2 N 67.2±1.4
FA7n3i CH3 (CH2)6CH3 0.4±0.04 52.2±1.3
FA8n3i CH3 (CH2)7CH3 N 89.8±3.7
FA9n3i CH3 (CH2)8CH3 N 86.7±5.3
FAB3i CH3 CH2phenyl 1.6±0.04 n
Propranolol 4.6±1.9 97.5±2.3

Overview of the studied 1-[3-(alkoxymethyl)-4-hydroxyphenyl]alkanones.

Substance Number Description R1 R2
1 EP1 CH2CH3 CH3
2 EP2 CH2CH3 CH2CH3
3 EP3 CH2CH3 (CH2)2CH3
4 EP3i CH2CH3 CH(CH3)2
5 EP4n CH2CH3 (CH2)3CH3
6 EP4i CH2CH3 CH2 CH (CH3)2
7 EP5n CH2CH3 (CH2)4CH3
8 EP5i CH2CH3 (CH2)2 CH(CH3)2
9 EP6n CH2CH3 (CH2)5CH3
10 EP7n CH2CH3 (CH2)6CH3
11 EP8n CH2CH3 (CH2)7CH3
12 EP9n CH2CH3 (CH2)8CH3
13 EP10n CH2CH3 (CH2)9CH3
14 EP5c CH2CH3 Cyclopentyl
15 EPbenz CH2CH3 CH2phenyl
16 EA1 CH3 CH3
17 EA2 CH3 CH2CH3
18 EA3n CH3 CH2CH2CH3
19 EA3i CH3 CH(CH3)2
20 EA4n CH3 (CH2)3CH3
21 EA5n CH3 (CH2)4CH3
22 EA7n CH3 (CH2)6CH3
23 EA8n CH3 (CH2)7CH3
24 EA9n CH3 (CH2)8CH3
25 EA5c CH3 Cyclopentyl
26 EAbenz CH3 CH2phenyl
27 4-OHacet
28 EAch

Antimicrobial activity of 1-[3-(alkoxymethyl)-4-hydroxyphenyl]alkanones.

Substance Number Description MIC (mmol/L) E.coli MIC (mmol/L) S. aureus
2 EP2 5.01 5.01
3 EP3n 2.46 n
6 EP4i 1.06 n
9 EP6n 0.38 n
12 EP9n 1.43 1.43
13 EP10n 0.77 0.13
14 EP5c 1.29 0.65
15 EPbenz 1.25 0.31
1a 4OHPr n n
18 EA4n 0.31 n
20 EA7n 0.94 n
21 EA8n 0.09 n
22 EA5c 4.11 2.05
28 EAch 0.53 n

Antioxidant activities of 1-[3-(alkoxymethyl)-4-hydroxyphenyl]alkanones.

Substance Number Description Inhibition DPPH [%]±SD Inhibition ABTS [%]±SD
1 EP1 n 3.9 ±0.04
2 EP2 2.5±0.1 8.5±0.4
3 EP3n 0.6±0.01 11.9±0.4
4 EP3i 3.7±0.02 28.1±0.3
6 EP4i 2.4±0.7 10.2±0.2
7 EP5n 1.8±1.3 1.3 ±0.4*
8 EP5i 12.6±0.6 5.8±0.7*
11 EP8n 6.2±0.7 n
13 EP10n 6.3±2.1 n
14 EP5c 3.3±0.03 25.0±1.6
15 EPbenzyl 3.3±0.9 1.5 ±0.3*
16 EA1 n 6.1±0.2
17 EA2 n 1.4±1.0
18 EA3n n 6.1±0.7
19 EA3i n 7.5±0.2
20 EA4n n 1.5± 1.0
21 EA5n 3.9±0.8 24.8±0.8
22 EA7n n 0.9±0.2*
23 EA8n n n
24 EA9n 3.9±0.7 n
25 EA5c n 8.4±0.7
26 EAbenzyl 1.59±1.4 16.7±0.7
27 4-OHacet n 0.9±0.01
28 EAch 4.32±2.5 8.2±0.4*
eISSN:
2453-6725
Language:
English
Publication timeframe:
2 times per year
Journal Subjects:
Pharmacy, other
Journal RSS Feed