Supplementary Information SIJ. Braz. Chem. Soc., Vol. 26, No. 9, S1-S20, 2015.

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*e-mail: sandrogreco.ufes@gmail.com

Synthesis, Antitumor Activity and Docking of 2,3-(Substituted)-1,4-Naphthoquinone Derivatives Containing Nitrogen, Oxygen and Sulfur

Maicon Delarmelina,a Renata D. Daltoé,c Murilo F. Cerri,c Klesia P. Madeira,c Leticia B. A. Rangel,c Valdemar Lacerda Júnior,a Wanderson Romão,b Alex G. Tarantod

and Sandro J. Greco*,a

aLaboratório de Síntese Orgânica & Medicinal and bLaboratório de Petroleômica e Química Forense, Departamento de Química, Universidade Federal do Espírito Santo, 29075-910 Vitória-ES, Brazil

cLaboratório de Biologia Celular do Câncer Humano, Departamento de Ciências Farmacêuticas, Universidade Federal do Espírito Santo, 29040-090 Vitória-ES, Brazil

dLaboratório de Modelagem Molecular, Universidade Federal de São João Del-Rei, 35501-296 Divinópolis-MG, Brazil

Figure S1. Infrared spectrum (KBr) of compound. 5a.

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Figure S2. 1H NMR spectrum (400 MHz, CDCl3) of compound 5a.

Figure S3. 13C NMR spectrum (101 MHz, CDCl3) of Compound 5a.

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Figure S4. Infrared spectrum (KBr) of compound 5b.

Figure S5. 1H NMR spectrum (400 MHz, CDCl3) of compound 5b.

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Figure S6. Infrared spectrum (KBr) of compound 5c.

Figure S7. 1H NMR spectrum (400 MHz, CDCl3) of compound 5c.

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Figure S8. 13C NMR spectrum (101 MHz, CDCl3) of compound 5c.

Figure S9. Infrared spectrum (KBr) of compound 5d.

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Figure S10. 1H NMR spectrum (400 MHz, CDCl3) of compound 5d.

Figure S11. 13C NMR spectrum (101 MHz, CDCl3) of compound 5d.

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Figure S12. Infrared spectrum (KBr) of compound 5e.

Figure S13. 1H NMR spectrum (400 MHz, CDCl3) of compound 5e.

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Figure S14. 13C NMR spectrum (101 MHz, CDCl3) of Compound 5e.

Figure S15. Infrared spectrum (KBr) of compound 5f.

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Figure S16. 1H NMR spectrum (400 MHz, CDCl3) of compound 5f.

Figure S17. 13C NMR spectrum (101 MHz, CDCl3) of compound 5f.

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Figure S18. Infrared spectrum (KBr) of compound 5g.

Figure S19. 1H NMR spectrum (400 MHz, CDCl3) of compound 5g.

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Figure S20. 13C NMR spectrum (101 MHz, CDCl3) of compound 5g.

Figure S21. Infrared spectrum (KBr) of compound 2.

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Figure S22. 1H NMR spectrum (400 MHz, CDCl3) of compound 2.

Figure S23. Infrared spectrum (KBr) of compound 6a.

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Figure S24. 1H NMR spectrum (400 MHz, CDCl3) of compound 6a.

Figure S25. 13C NMR spectrum (101 MHz, CDCl3) of compound 6a.

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Figure S26. Infrared spectrum (KBr) of compound 6b.

Figure S27. 1H NMR spectrum (400 MHz, CDCl3) of compound 6b.

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Figure S28. Infrared spectrum (KBr) of compound 6c.

Figure S29. 1H NMR spectrum (400 MHz, CDCl3) of compound 6c.

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Figure S30. Infrared spectrum (KBr) of compound 8.

Figure S31. 1H NMR spectrum (400 MHz, CDCl3) of compound 8.

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Figure S32. 13C NMR spectrum (101 MHz, CDCl3) of compound 8.

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Figure S33. ESI(+)-FT-ICR MS spectra for compounds 5a-d.

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Figure S34. ESI(±)-FT-ICR MS spectra for compounds 5e-g.

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Figure S35. ESI(+)-FT-ICR MS spectra for compounds 6a-c and 8.