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

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

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

Table 2

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

[i] n = non-measurable values, compounds not active against Candida albicans

Table 3

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^*

* concentration 10⁻³ mol.dm⁻³ n = non-measurable values

Table 4

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

[i] n = non-measurable values

Table 5

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

[i] n = non-measurable values

References

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Articles in this issue

DOI: https://doi.org/10.2478/afpuc-2020-0012 | Journal eISSN: 2453-6725 (formerly 1338-6786) | Journal ISSN: 0301-2298

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Language: English

Page range: 34 - 44

Submitted on: Apr 4, 2020

Published on: Mar 11, 2021

Published by: Comenius University in Bratislava, Faculty of Pharmacy

In partnership with: Paradigm Publishing Services

Keywords:

substituted phenols,

antimicrobial activity,

antioxidant activity,

antiradical activity

Related subjects:

Pharmacy,

Pharmacy, other

© 2021 R. Čižmáriková, M. Markuliak, L. Habala, J. Valentová, A. Bilková, published by Comenius University in Bratislava, Faculty of Pharmacy
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Volume 67 (2020): Issue 2 (May 2020)

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

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Table 5

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