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, University of Osijek, Vladimira Preloga 1, HR–31000 Osijek, 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 , 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