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Synthesis and Correlation of Aggregation and Antimicrobial Properties of Homochiral Quaternary Ammonium Bromides Derived from Camphoric Acid Cover

Synthesis and Correlation of Aggregation and Antimicrobial Properties of Homochiral Quaternary Ammonium Bromides Derived from Camphoric Acid

European Pharmaceutical Journal
Volume 68 (2021): Issue 1 (January 2021)
By: ,   and    
Open Access
|Apr 2021
Figures & tables

Figures & Tables

Figure 1

Synthesis of QASs derived from (1R,3S)-(+)-camphoric acid.

Table 1

Characterization of camphoric acid-derived QAS 1.

CompoundFormula / [α]D21 (conc[g/100 mL]., solvent)wi(calc.)/%
wi(found)/%		YieldM.p.
CHN%°C
1aC26H49BrN2O2/+7.99 (0.85, CHCl3)62.26
62.34		9.85
9.81		5.58
5.61		8082–83.5
1bC28H53BrN2O2/+6.75 (0.809, CHCl3)63.50
63.26		10.09
9.96		5.29
5.15		8785–85.5
1cC30H57BrN2O2/+7.2 (c = 0.799, CHCl3)64.61
64.36		10.30
9.96		5.02
4.85		8495–96.8
1dC32H61BrN2O2/+6,7d (c = 0.80, CHCl3)65.62
65.68		10.50
10.45		4.78
4.82		8596.8–97.5
Table 2

Spectroscopic data of camphoric acid-derived QASs 1.

CompoundSpectral data
1aIR, ν˜ /cm−1: 2921, 2843, 1723, 1669, 1469, 1373, 1343, 1332, 1179, 1002, 929, 823, 724
1H NMR (300 MHz, CDCl3) δ: 0.88 (t, 3H, J = 7.04 Hz), 0.95 (s, 3H), 0.99 (s, 3H), 1.20 (s, 3H), 1.26 (s, 13H), 1.37 (s, 4H), 1.77 (s, 2H, broad), 1.88–2.11 (m, 4H), 2.17–2.29 (m, 1H), 2.74 (d, 1H, J = 7.04 Hz), 3.51 (s, 6H), 3.60–3.70 (m, 4H), 4.11 (t, 2H, J = 8.21 Hz)
13C NMR (75 MHz, CDCl3) δ: 13.9; 14.1; 19.5; 21.9; 22.7; 22.8; 25.1; 26.2; 29.2; 29.3; 29.4; 29.5; 29.6 (2C); 31.9; 32.9; 34.0; 44.7; 51.7 (2C); 54.6; 56.2; 60.0; 64.1; 176.0; 178.2
1bIR, ν˜ /cm−1: 2919, 2849, 1723, 1668, 1469, 1373, 1344, 1331, 1179, 989, 927, 822, 723
1H NMR (300 MHz, CDCl3) δ: 0.89 (t, 3H, J = 6.45 Hz), 0.96 (s, 3H), 0.99 (s, 3H), 1.21 (s, 3H), 1.27 (s, 15H), 1.38 (s, 4H), 1.74–2.12 (m, 8H), 2.19–2.33 (m, 1H), 2.76 (d, 1H, J = 6.45 Hz), 3.52 (s, 6H), 3.59–3.70 (m, 4H), 4.11 (t, 2H, J = 7.62 Hz)
13C NMR (75 MHz, CDCl3) δ: 13.9; 14.2; 19.5; 21.9; 22.7; 22.8; 25.1; 26.2; 29.3; 29.4 (2C); 29.5; 29.7 (4C); 31.9; 32.9; 34.0; 44.7; 51.8 (2C); 54.6; 56.2; 60.0; 64.1; 176.0; 178.3
1cIR, ν˜ /cm−1: 2918, 2849, 1723, 1669, 1469, 1373, 1344, 1331, 1179, 990, 925, 820, 722
1H NMR (300 MHz, CDCl3) δ: 0.88 (t, 3H, J = 6.45 Hz), 0.95 (s, 3H), 0.99 (s, 3H), 1.20 (s, 3H), 1.25 (s, 21H), 1.37 (s, 4H), 1.77 (s, 2H, broad), 1.85–2.11 (m, 4H), 2.17–2.30 (m, 1H), 2.75 (d, 1H, J = 6.45 Hz), 3.51 (s, 6H), 3.56–3.70 (m, 4H), 4.11 (t, 2H, J = 7.62 Hz)
13C NMR (75 MHz, CDCl3) δ: 13.9; 14.1; 19.5; 21.9; 22.7; 22.8; 25.1; 26.2; 29.3; 29.4 (2C); 29.5; 29.7 (6C); 31.9; 32.9; 34.0; 44.6; 51.7 (2C); 54.5; 56.2; 60.0; 64.1; 176.0; 178.2
1dIR, ν˜ /cm−1: 2918, 2848, 1723, 1668, 1469, 1373, 1344, 1331, 1179, 1001, 927, 820, 721
1H NMR (300 MHz, CDCl3) δ: 0.88 (t, 3H, J = 6.45 Hz), 0.95 (s, 3H), 0.99 (s, 3H), 1.20 (s, 3H), 1.25 (s, 27H), 1.37 (s, 2H), 1.77 (s, 2H, broad), 1.85–2.11 (m, 4H), 2.17–2.30 (m, 1H), 2.74 (d, 1H, J = 6.45 Hz), 3.51 (s, 6H), 3.59–3.70 (m, 4H), 4.11 (t, 2H, J = 7.04 Hz)
13C NMR (75 MHz, CDCl3) δ: 13.9; 14.1; 19.5; 21.9; 22.7; 22.8; 25.1; 26.2; 29.2; 29.4 (2C); 29.5; 29.7 (8C); 31.9; 32.9; 34.0; 44.6; 51.7 (2C); 54.5; 56.2; 60.0; 64.1; 176.0; 178.2
Table 3

Minimal inhibitory concentrations [μmol L−1] of prepared QAS 1.

CompoundS. aureus CNCTC 29/58E. coli CNCTC 377/79NC. albicans CCM 8186
1a6.124.312.2
1b0.75.80.7
1c0.65.50.6
1d324.1665.8324.1
BAB2626026
Figure 2

Surface tension versus the logarithm of the aqueous molar concentration of 1a–1d at 25°C.

Table 4

CMC, g(CMC) and pC20 values of prepared QASs calculated from tensiometry measurements.

1a1b1c1d
CMC [molL−1]5.07×10−3±0.23×10−39.13×10−4±0.98×10−40.97×10−4±0.05×10−48.09×10−6±1.13×10−6
γ(CMC) [mNm−1]36.3637.3238.4942.51
pC203.54.15.15.5
Figure 3

Variation of log CMC with chain length of 1a–1d at 25°C.

Figure 4

Correlation of CMC [mmolL−1] and MIC [mmolL−1] of QASs 1a–1d for a) S. aureus; b) E. coli; c) C. albicans.

DOI: https://doi.org/10.2478/afpuc-2020-0017 | Journal eISSN: 2453-6725 (formerly 1338-6786) | Journal ISSN: 0301-2298
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Language: English
Page range: 10 - 16
Submitted on: Nov 25, 2020
Accepted on: Feb 12, 2021
Published on: Apr 23, 2021
Published by: Comenius University in Bratislava, Faculty of Pharmacy
In partnership with: Paradigm Publishing Services
Keywords:
quaternary ammonium salts,
antimicrobial activity,
camphoric acid,
critical micelle concentration
Related subjects:
Pharmacy,
Pharmacy, other

© 2021 R. Mikláš, N. Miklášová, M. Bukovský, published by Comenius University in Bratislava, Faculty of Pharmacy
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Volume 68 (2021): Issue 1 (January 2021)
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