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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: [email protected], [email protected]
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Figure S1. FTIR (KBr) spectrum of compound 13a.
Figure S2. 1H NMR spectrum (500 MHz, CDCl3) of compound 13a.
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Figure S3. 13
C NMR spectrum (125 MHz, CDCl3) of compound 13a.
Figure S4. Mass spectrum of compound 13a.
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Figure S5. FTIR (KBr) spectrum of compound 13c.
Figure S6. 1H NMR spectrum (500 MHz, CDCl3) of compound 13c.
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Figure S7. 13
C NMR spectrum (100 MHz, DMSO-d6) of compound 13c.
Figure S8. Mass spectrum of compound 13c.
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Figure S9. FTIR (KBr) spectrum of compound 13d.
Figure S10. 1H NMR spectrum (500 MHz, CDCl3) of compound 13d.
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Figure S11. 13
C NMR spectrum (100 MHz, DMSO-d6) of compound 13d.
Figure S12. Mass spectrum of compound 13d.
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Figure S13. FTIR (KBr) spectrum of compound 13e.
Figure S14. 1H NMR spectrum (500 MHz, CDCl3) of compound 13e.
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Figure S15. 13
C NMR spectrum (100 MHz, DMSO-d6) of compound 13e.
Figure S16. Mass spectrum of compound 13e.
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Figure S17. FTIR (KBr) spectrum of compound 13f.
Figure S18. 1H NMR spectrum (500 MHz, CDCl3) of compound 13f.
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Figure S19. 13
C NMR spectrum (100 MHz, DMSO-d6) of compound 13f.
Figure S20. Mass spectrum of compound 13f.
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Figure S21. FTIR (KBr) spectrum of compound 13g.
Figure S22. 1H NMR spectrum (500 MHz, CDCl3) of compound 13g.
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Figure S23. 13
C NMR spectrum (100 MHz, DMSO-d6) of compound 13g.
Figure S24. Mass spectrum of compound 13g.
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Figure S25. FTIR (KBr) spectrum of compound 13h.
Figure S26. 1H NMR spectrum (500 MHz, CDCl3) of compound 13h.
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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.
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Figure S29. FTIR (KBr) spectrum of compound 13i.
Figure S30. 1H NMR spectrum (500 MHz, CDCl3) of compound 13i.
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Figure S31. 13
C NMR spectrum (100 MHz, DMSO-d6) of compound 13i.
Figure S32. Mass spectrum of compound 13i.
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Figure S33. FTIR (KBr) spectrum of compound 13j.
Figure S34. 1H NMR spectrum (500 MHz, CDCl3) of compound 13j.
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Figure S35. 13
C NMR spectrum (100 MHz, DMSO-d6) of compound 13j.
Figure S36. Mass spectrum of compound 13j.
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Figure S37. FTIR (KBr) spectrum of compound 13k.
Figure S38. 1H NMR spectrum (500 MHz, CDCl3) of compound 13k.
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Figure S39. 13
C NMR spectrum (100 MHz, DMSO-d6) of compound 13k.
Figure S40. Mass spectrum of compound 13l.
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Figure S41. FTIR (KBr) spectrum of compound 13l.
Figure S42. 1H NMR spectrum (500 MHz, CDCl3) of compound 13l.
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Figure S43. 13
C NMR spectrum (100 MHz, DMSO-d6) of compound 13l.
Figure S44. Mass spectrum of compound 13l.
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Figure S45. FTIR (KBr) spectrum of compound 13m.
Figure S46. 1H NMR spectrum (500 MHz, CDCl3) of compound 13m.
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Figure S47. 13
C NMR spectrum (100 MHz, DMSO-d6) of compound 13m.
Figure S48. Mass spectrum of compound 13m.
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Figure S49. FTIR (KBr) spectrum of compound 13n.
Figure S50. 1H NMR spectrum (500 MHz, CDCl3) of compound 13n.
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Figure S51. 13
C NMR spectrum (100 MHz, DMSO-d6) of compound 13n.
Figure S52. Mass spectrum of compound 13n.