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1 Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications. This journal is The Royal Society of Chemistry 2014 Supporting information Naphthoquinone-based Chalcone Hybrids and derivatives: Synthesis and Potent Activity Against Cancer Cell Lines Guilherme A. M. Jardim, a Tiago T. Guimarães, b Maria do Carmo F. R. Pinto, c Bruno C. Cavalcanti, d Kaio M. de Farias, d Claudia Pessoa d Divya K. Nair, e Irishi N. N. Namboothiri, e* and Eufrânio N. da Silva Júnior a* a Institute of Exact Sciences, Department of Chemistry, Federal University of Minas Gerais, CEP , Belo Horizonte-MG, Brazil. Phone: ; Fax: ; b Instituto Nacional de Câncer, Hospital do Câncer - Unidade I - Seção de Medicina Nuclear, , Rio de Janeiro, RJ, Brazil; c Núcleo de Pesquisas de Produtos Naturais, UFRJ, , Rio de Janeiro, RJ, Brazil; d Departamento de Fisiologia e Farmacologia, UFC, , Fortaleza, CE, Brazil; e Department of Chemistry, Indian Institute of Technology Bombay, Mumbai , India. Phone: ; Fax: Fax: eufranio@ufmg.br and irishi@iitb.ac.in Contents A) NMR spectra of unpublished compounds S2 B) NMR spectra of previously published compounds S12 S1
2 1) Compound 10 Figure 1. 1 H NMR spectrum (500 MHz, CDCl 3 ) of compound 10. Figure C-APT NMR spectrum (125 MHz, CDCl 3 ) of compound 10. S2
3 2) Compound 11 Figure 3. 1 H NMR spectrum (400 MHz, CDCl 3 ) of compound 11. Figure C-APT NMR spectrum (100 MHz, CDCl 3 ) of compound 11. S3
4 3) Compound 12 Figure 5. 1 H NMR spectrum (400 MHz, CDCl 3 ) of compound 12. Figure C-APT NMR spectrum (100 MHz, CDCl 3 ) of compound 12. S4
5 4) Compound 13 Figure 7. 1 H NMR spectrum (400 MHz, CDCl 3 ) of compound Figure C NMR spectrum (100 MHz, CDCl 3 ) of compound 13. S5
6 5) Compound 14 Figure 9. 1 H NMR spectrum (400 MHz, CDCl 3 ) of compound 14. Figure C-APT NMR spectrum (100 MHz, CDCl 3 ) of compound 14. S6
7 6) Compound 15 Figure H NMR spectrum (400 MHz, CDCl 3 ) of compound 15. Figure C-APT NMR spectrum (100 MHz, CDCl 3 ) of compound 15. S7
8 7) Compound 30 Figure H NMR spectrum (200 MHz, CDCl 3 ) of compound 30. Figure C NMR spectrum (50 MHz, CDCl 3 ) of compound 30. S8
9 8) Compound 35 Figure H NMR spectrum (200 MHz, CDCl 3 ) of compound 35. Figure C NMR spectrum (50 MHz, CDCl 3 ) of compound 35. S9
10 9) Compound 37 Figure H NMR spectrum (200 MHz, CDCl 3 ) of compound 37. Figure C NMR spectrum (50 MHz, CDCl 3 ) of compound 37. S10
11 10) Compound 39 Figure H NMR spectrum (200 MHz, CDCl 3 ) of compound 39. Figure C NMR spectrum (50 MHz, CDCl 3 ) of compound 39. S11
12 11) Compound 1 Figure H NMR spectrum (300 MHz, CDCl 3 ) of compound 1. Figure C-APT NMR spectrum (50 MHz, CDCl 3 ) of compound 1. S12
13 12) Compound 2 Figure H NMR spectrum (300 MHz, CDCl 3 ) of compound Figure C NMR spectrum (50 MHz, CDCl 3 ) of compound 2. S13
14 13) Compound 3 Figure H NMR spectrum (300 MHz, CDCl 3 ) of compound 3. Figure C NMR spectrum (50 MHz, CDCl 3 ) of compound 3. S14
15 14) Compound 4 Figure H NMR spectrum (300 MHz, CDCl 3 ) of compound 4. Figure C NMR spectrum (50 MHz, DMSO-d 6 ) of compound 4. S15
16 15) Compound 5 Figure H NMR spectrum (300 MHz, CDCl 3 ) of compound 5. Figure C NMR spectrum (50 MHz, CDCl 3 ) of compound 5. S16
17 16) Compound 6 Figure H NMR spectrum (300 MHz, CDCl 3 ) of compound 6. Figure C-APT NMR spectrum (75 MHz, CDCl 3 ) of compound 6. S17
18 17) Compound 16 Figure H NMR spectrum (500 MHz, CDCl 3 ) of compound 16. Figure C NMR spectrum (125 MHz, CDCl 3 ) of compound 16. S18
19 18) Compound 17 Figure H NMR spectrum (500 MHz, CDCl 3 ) of compound 17. Figure C NMR spectrum (125 MHz, CDCl 3 ) of compound 17. S19
20 19) Compound 18 Figure H NMR spectrum (500 MHz, CDCl 3 ) of compound 18. Figure C NMR spectrum (125 MHz, CDCl 3 ) of compound 18. S20
21 20) Compound 19 Figure H NMR spectrum (500 MHz, CDCl 3 ) of compound 19. Figure C NMR spectrum (125 MHz, CDCl 3 ) of compound 19. S21
22 21) Compound 20 Figure H NMR spectrum (500 MHz, CDCl 3 ) of compound 20. Figure C NMR spectrum (125 MHz, CDCl 3 ) of compound 20. S22
23 22) Compound 21 Figure H NMR spectrum (500 MHz, CDCl 3 ) of compound 21. Figure C NMR spectrum (125 MHz, CDCl 3 ) of compound 21. S23
24 23) Compound 22 Figure H NMR spectrum (500 MHz, CDCl 3 ) of compound 22. Figure C NMR spectrum (125 MHz, CDCl 3 ) of compound 22. S24
25 24) Compound 23 Figure H NMR spectrum (500 MHz, CDCl 3 ) of compound 23. Figure C NMR spectrum (125 MHz, CDCl 3 ) of compound 23. S25
26 25) Compound 24 Figure H NMR spectrum (500 MHz, CDCl 3 ) of compound 24. Figure C NMR spectrum (125 MHz, CDCl 3 ) of compound 24. S26
27 26) Compound 25 Figure H NMR spectrum (500 MHz, CDCl 3 ) of compound 25. Figure C NMR spectrum (125 MHz, CDCl 3 ) of compound 25. S27
28 27) Compound 29 Figure H NMR spectrum (200 MHz, CDCl 3 ) of compound 29. Figure C NMR spectrum (50 MHz, CDCl 3 ) of compound 29. S28
29 28) Compound 31 Figure H NMR spectrum (200 MHz, CDCl 3 ) of compound Figure C NMR spectrum (50 MHz, CDCl 3 ) of compound 31. S29
30 29) Compound 33 Figure H NMR spectrum (200 MHz, CDCl 3 ) of compound 33. Figure C NMR spectrum (50 MHz, CDCl 3 ) of compound 33. S30
31 30) Compound 41 Figure H NMR spectrum (300 MHz, DMSO-d 6 ) of compound 41. Figure C-APT NMR spectrum (75 MHz, DMSO-d 6 ) of compound 41. S31
32 31) Compound 42 Figure H NMR spectrum (300 MHz, DMSO-d 6 ) of compound 42. Figure C-APT NMR spectrum (75 MHz, DMSO-d 6 ) of compound 42. S32
33 32) Compound 43 Figure H NMR spectrum (300 MHz, DMSO-d 6 ) of compound 43. Figure C-APT NMR spectrum (75 MHz, DMSO-d 6 ) of compound 43. S33
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