Supplementary Information

Inhibition of Zika Virus Replication by Synthetic Bis-Naphthoquinones

Daniel T. G. Gonzaga,a,b

Rafaela S. P. Gomes,c Roberta K. F. Marra,

a Fernando C. da Silva,

a Max W.

L. Gomes,c Davis F. Ferreira,

d,e Raissa M. A. Santos,

a Ana M. V. Pinto,

f Norman Arthur Ratcliffe,

g

Claudio C. Cirne-Santos,c Caroline S. Barros,

c Vitor F. Ferreira*,a

and Izabel Christina N. P. Paixão *,c

aInstituto de Química, Universidade Federal Fluminense, 24020-141 Niteroi-RJ, Brazil

bInstituto Biomédico, Centro Universitário Estadual da Zona Oeste, 23070-200 Rio de Janeiro-RJ, Brazil

cInstituto de Biologia, Universidade Federal Fluminense, 24020-141 Niteroi-RJ, Brazil

dInstituto de Microbiologia Prof. Paulo de Góes, Universidade Federal do Rio de Janeiro, 21941-599

Rio de Janeiro-RJ, Brazil

eDepartment of Molecular and Structural Biochemistry, North Carolina State University,

120 W Broughton Dr, Raleigh, 27607 NC, USA

fUnidade de Farmácia, Universidade Federal Fluminense, 24210-130 Niteroi-RJ, Brazil

gDepartment of Biociences, College of Science Swansea University, SA2 8PP Swansea, UK

____________________________________________________

*e-mail: izabeluff@gmail.com, vitorferreira@id.uff.br

Figure S1. FTIR (KBr) spectrum of compound 13a.

Figure S2. 1H NMR spectrum (500 MHz, CDCl3) of compound 13a.

Figure S3. 13

C NMR spectrum (125 MHz, CDCl3) of compound 13a.

Figure S4. Mass spectrum of compound 13a.

Figure S5. FTIR (KBr) spectrum of compound 13c.

Figure S6. 1H NMR spectrum (500 MHz, CDCl3) of compound 13c.

Figure S7. 13

C NMR spectrum (100 MHz, DMSO-d6) of compound 13c.

Figure S8. Mass spectrum of compound 13c.

Figure S9. FTIR (KBr) spectrum of compound 13d.

Figure S10. 1H NMR spectrum (500 MHz, CDCl3) of compound 13d.

Figure S11. 13

C NMR spectrum (100 MHz, DMSO-d6) of compound 13d.

Figure S12. Mass spectrum of compound 13d.

Figure S13. FTIR (KBr) spectrum of compound 13e.

Figure S14. 1H NMR spectrum (500 MHz, CDCl3) of compound 13e.

Figure S15. 13

C NMR spectrum (100 MHz, DMSO-d6) of compound 13e.

Figure S16. Mass spectrum of compound 13e.

Figure S17. FTIR (KBr) spectrum of compound 13f.

Figure S18. 1H NMR spectrum (500 MHz, CDCl3) of compound 13f.

Figure S19. 13

C NMR spectrum (100 MHz, DMSO-d6) of compound 13f.

Figure S20. Mass spectrum of compound 13f.

Figure S21. FTIR (KBr) spectrum of compound 13g.

Figure S22. 1H NMR spectrum (500 MHz, CDCl3) of compound 13g.

Figure S23. 13

C NMR spectrum (100 MHz, DMSO-d6) of compound 13g.

Figure S24. Mass spectrum of compound 13g.

Figure S25. FTIR (KBr) spectrum of compound 13h.

Figure S26. 1H NMR spectrum (500 MHz, CDCl3) of compound 13h.

Figure S27. 13

C NMR spectrum (100 MHz, DMSO-d6) of compound 13g.

Figure S28. 13

C NMR spectrum (100 MHz, DMSO-d6) of compound 13h.

Figure S29. FTIR (KBr) spectrum of compound 13i.

Figure S30. 1H NMR spectrum (500 MHz, CDCl3) of compound 13i.

Figure S31. 13

C NMR spectrum (100 MHz, DMSO-d6) of compound 13i.

Figure S32. Mass spectrum of compound 13i.

Figure S33. FTIR (KBr) spectrum of compound 13j.

Figure S34. 1H NMR spectrum (500 MHz, CDCl3) of compound 13j.

Figure S35. 13

C NMR spectrum (100 MHz, DMSO-d6) of compound 13j.

Figure S36. Mass spectrum of compound 13j.

Figure S37. FTIR (KBr) spectrum of compound 13k.

Figure S38. 1H NMR spectrum (500 MHz, CDCl3) of compound 13k.

Figure S39. 13

C NMR spectrum (100 MHz, DMSO-d6) of compound 13k.

Figure S40. Mass spectrum of compound 13l.

Figure S41. FTIR (KBr) spectrum of compound 13l.

Figure S42. 1H NMR spectrum (500 MHz, CDCl3) of compound 13l.

Figure S43. 13

C NMR spectrum (100 MHz, DMSO-d6) of compound 13l.

Figure S44. Mass spectrum of compound 13l.

Figure S45. FTIR (KBr) spectrum of compound 13m.

Figure S46. 1H NMR spectrum (500 MHz, CDCl3) of compound 13m.

Figure S47. 13

C NMR spectrum (100 MHz, DMSO-d6) of compound 13m.

Figure S48. Mass spectrum of compound 13m.

Figure S49. FTIR (KBr) spectrum of compound 13n.

Figure S50. 1H NMR spectrum (500 MHz, CDCl3) of compound 13n.

Figure S51. 13

C NMR spectrum (100 MHz, DMSO-d6) of compound 13n.

Figure S52. Mass spectrum of compound 13n.