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

R. Mikláš
R. Mikláš
, 
N. Miklášová
N. Miklášová
 e 
M. Bukovský
M. Bukovský
   | 23 apr 2021
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Article Category: Original Paper
Pubblicato online: 23 apr 2021
Pagine: 10 - 16
Ricevuto: 25 nov 2020
Accettato: 12 feb 2021
DOI: https://doi.org/10.2478/afpuc-2020-0017
Parole chiave
© 2021 R. Mikláš et al., published by Sciendo
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Figure 1

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

Figure 2

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

Figure 3

Variation of log CMC with chain length of 1a–1d at 25°C.
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.
Correlation of CMC [mmolL−1] and MIC [mmolL−1] of QASs 1a–1d for a) S. aureus; b) E. coli; c) C. albicans.

Characterization of camphoric acid-derived QAS 1.

Compound Formula / [α]D21 (conc[g/100 mL]., solvent) wi(calc.)/%wi(found)/% Yield M.p.
C H N % °C
1a C26H49BrN2O2/+7.99 (0.85, CHCl3) 62.2662.34 9.859.81 5.585.61 80 82–83.5
1b C28H53BrN2O2/+6.75 (0.809, CHCl3) 63.5063.26 10.099.96 5.295.15 87 85–85.5
1c C30H57BrN2O2/+7.2 (c = 0.799, CHCl3) 64.6164.36 10.309.96 5.024.85 84 95–96.8
1d C32H61BrN2O2/+6,7d (c = 0.80, CHCl3) 65.6265.68 10.5010.45 4.784.82 85 96.8–97.5

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

Compound S. aureus CNCTC 29/58 E. coli CNCTC 377/79N C. albicans CCM 8186
1a 6.1 24.3 12.2
1b 0.7 5.8 0.7
1c 0.6 5.5 0.6
1d 324.1 665.8 324.1
BAB 26 260 26

Spectroscopic data of camphoric acid-derived QASs 1.

Compound Spectral data
1a IR, ν˜ \tilde \nu /cm−1: 2921, 2843, 1723, 1669, 1469, 1373, 1343, 1332, 1179, 1002, 929, 823, 7241H 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
1b IR, ν˜ \tilde \nu /cm−1: 2919, 2849, 1723, 1668, 1469, 1373, 1344, 1331, 1179, 989, 927, 822, 7231H 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
1c IR, ν˜ \tilde \nu /cm−1: 2918, 2849, 1723, 1669, 1469, 1373, 1344, 1331, 1179, 990, 925, 820, 7221H 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
1d IR, ν˜ \tilde \nu /cm−1: 2918, 2848, 1723, 1668, 1469, 1373, 1344, 1331, 1179, 1001, 927, 820, 7211H 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

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

1a 1b 1c 1d
CMC [molL−1] 5.07×10−3±0.23×10−3 9.13×10−4±0.98×10−4 0.97×10−4±0.05×10−4 8.09×10−6±1.13×10−6
γ(CMC) [mNm−1] 36.36 37.32 38.49 42.51
pC20 3.5 4.1 5.1 5.5
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