Supporting Information
An Improved, Efficient Method for the Quaternization of Nicotinamide and Antifungal Activities of Its Derivatives
Tamara Siber1, Valentina Bušić2, Dora Zobundžija2, Sunčica Roca3, Dražen Vikić-Topić3, Karolina Vrandečić1 andDajana Gašo-Sokač2*
1 Faculty of Agrobiotechnical Sciences, Josip Juraj Strossmayer University of Osijek, Vladimira Preloga 1, HR–31000 Osijek, Croatia 2 Faculty of Food Technology, Josip Juraj Strossmayer University of Osijek, Kuhačeva 20, HR–31000 Osijek, Croatia 3 NMR Centre, Ruđer Bošković Institute, Bijenička cesta 54, HR–10000 Zagreb, Croatia Department of Natural and Health Sciences, Juraj Dobrila University of Pula, Zagrebačka 30, HR– 52100 Pula, Croatia *Correspondence: [email protected]; Tel.: +385-31-224327.
Contents
I) Copies of 1H- and 13C-NMR spectra ...... 1 II) Copies of 1H-1H COSY NMR spectra of compounds (2) and (8) ...... 11 III) Copy of 1H-13C HMQC NMR spectrum of compound (8) ...... 12 IV) Copies of 1H-13C HMBC NMR spectra of compounds (2), (3) and (9) ...... 13
I) Copies of 1H- and 13C-NMR spectra
I
(1)
1 Figure S1. H NMR (600 MHz, DMSO-d6) spectrum of the compound (1).
13 Figure S2. C APT NMR (150 MHz, DMSO-d6) spectrum of the compound (1).
1
Br
(2)
1 Figure S3. H NMR (600 MHz, DMSO-d6) spectrum of the compound (2).
13 Figure S4. C APT NMR (150 MHz, DMSO-d6) spectrum of the compound (2).
2
Br
(3)
1 Figure S5. H NMR (600 MHz, DMSO-d6) spectrum of the compound (3).
13 Figure S6. C APT NMR (150 MHz, DMSO-d6) spectrum of the compound (3).
3
Br
(4)
1 Figure S7. H NMR (600 MHz, DMSO-d6) spectrum of the compound (4).
13 Figure S8. C APT NMR (150 MHz, DMSO-d6) spectrum of the compound (4).
4
Br
(5)
1 Figure S9. H NMR (600 MHz, DMSO-d6) spectrum of the compound (5).
13 Figure S10. C APT NMR (150 MHz, DMSO-d6) spectrum of the compound (5).
5
Br
(6)
1 Figure S11. H NMR (600 MHz, DMSO-d6) spectrum of the compound (6).
13 Figure S12. C APT NMR (150 MHz, DMSO-d6) spectrum of the compound (6).
6
Br
(7)
1 Figure S13. H NMR (600 MHz, DMSO-d6) spectrum of the compound (7).
13 Figure S14. C APT NMR (150 MHz, DMSO-d6) spectrum of the compound (7).
7
Br
(8)
1 Figure S15. H NMR (600 MHz, DMSO-d6) spectrum of the compound (8).
13 Figure S16. C APT NMR (150 MHz, DMSO-d6) spectrum of the compound (8).
8
Br
(9)
1 Figure S17. H NMR (600 MHz, DMSO-d6) spectrum of the compound (9).
13 Figure S18. C APT NMR (150 MHz, DMSO-d6) spectrum of the compound (9).
9
Br
(10)
1 Figure S19. H NMR (600 MHz, DMSO-d6) spectrum of the compound (10).
13 Figure S20. C APT NMR (150 MHz, DMSO-d6) spectrum of the compound (10).
10
II) Copies of 1H-1H COSY NMR spectra of compounds (2) and (8)
Br
(2)
1 1 Figure S21. H- H COSY NMR (600 MHz, DMSO-d6) spectrum of the compound (2). The one-dimensional 1H NMR spectra are shown at the top and at the left-hand edge.
CONH2
N+ Br
O (8)
1 1 Figure S22. H- H COSY NMR (600 MHz, DMSO-d6) spectrum of the compound (8). The one-dimensional 1H NMR spectra are shown at the top and at the left-hand edge.
11
III) Copy of 1H-13C HMQC NMR spectrum of compound (8)
Br
(8)
1 13 Figure S23. H- C HMQC NMR spectrum of compound (8) in DMSO-d6. The one-dimensional 600 MHz 1H NMR spectrum is shown at the top edge and the 150 MHz 13C NMR spectrum at the left-hand edge.
12
IV) Copies of 1H-13C HMBC NMR spectra of compounds (2), (3) and (9)
CONH2
Cl N+ Br
O
(2)
1 13 Figure S24. H- C HMBC NMR spectrum of compound (2) in DMSO-d6. The one-dimensional 600 MHz 1H NMR spectrum is shown at the top edge and the 150 MHz 13C NMR spectrum at the left- hand edge.
13
Br
(3)
1 13 Figure S25. H- C HMBC NMR spectrum of compound (3) in DMSO-d6. The one-dimensional 600 MHz 1H NMR spectrum is shown at the top edge and the 150 MHz 13C NMR spectrum at the left- hand edge.
14
Br
(9)
1 13 Figure S26. H- C HMBC NMR spectrum of compound (9) in DMSO-d6. The one-dimensional 600 MHz 1H NMR spectrum is shown at the top edge and the 150 MHz 13C NMR spectrum at the left- hand edge.
15