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1 Supplementary Information J. Braz. Chem. Soc., Vol. 26, No. 6, S1-S29, Printed in Brazil Sociedade Brasileira de Química $ SI Marina Ritter,*,a Rosiane M. Martins, a Silvana A. Rosa, a Juliana L. Malavolta, b Rafael G. Lund, c Alex F. C. Flores d and Claudio M. P. Pereira*,a a Laboratory of Bioactive Heterocycles (LAHBBIO), Center of Chemical, Pharmaceutical and Food Sciences, Federal University of Pelotas, Capão do Leão-RS, Brazil b Federal University of Santa Maria, Santa Maria-RS, Brazil c Laboratory of Microbiology, School of Dentistry, Federal University of Pelotas, Pelotas-RS, Brazil d School of Chemistry and Food, Federal University of Rio Grande, Rio Grande-RS, Brazil Data of chalcones 3a-n (E)-1,3-Diphenylprop-2-en-1-one (3a) mp C; IR (KBr) n max / cm , , , , , , , , , ; 1 H NMR (400 MHz, CDCl 3 ) d (m, 3H, Ph-H), (m, 2H, Ph H), 7.50 (d, 1H, J Hz, Hα), (m, 3H, Ar), 7,79 (d, 1H, J Hz, Hβ), (m, 2H, Ph-H); 13 C NMR (100 MHz, CDCl 3 ) d , , , , , , , , , ; GC-MS m/z, observed: ; C 15 H 12 O [M] + requires: Figure S1. Mass spectrum of compound 3a. * mritter.quimica@gmail.com, claudio.martin@pq.cnpq.br
2 S2 J. Braz. Chem. Soc. Figure S2. FTIR (KBr) spectrum of compound 3a. Figure S3. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 3a.
3 Vol. 26, No. 6, 2015 Ritter et al. S3 Figure S4. 13 C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 3a. (E)-3-(4-Methoxyphenyl)-1-phenylprop-2-en-1-one (3b) mp C; IR (KBr) n max / cm , , , , , , , , , , , , , , ; 1 H NMR (400 MHz, CDCl 3 ) d 3.80 (s, 3H, CH 3 ), 6.90 (d, 2H, J 8.69 Hz, Ar), 7.38 (d, 1H, J Hz, Hα), (m, 5H, Ph H), 7.76 (d, 1H, J Hz, Hβ), 7.98 (d, 2H, J 7.29 Hz, Ph-H); 13 C NMR (100 MHz, CDCl-d 6 ) d 54.88, , , , , , , , , , , ; GC-MS m/z, observed: ; C 16 H 14 O 2 [M] + requires: Figure S5. Mass spectrum of compound 3b.
4 S4 J. Braz. Chem. Soc. Figure S6. FTIR (KBr) spectrum of compound 3b. Figure S7. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 3b.
5 Vol. 26, No. 6, 2015 Ritter et al. S5 Figure S8. 13 C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 3b. (E)-3-(4-Fluorophenyl)-1-phenylprop-2-en-1-one (3c) mp C; IR (KBr) n max / cm , , , , , , , , , ; 1 H NMR (400 MHz, CDCl 3 ) d 7.09 (t, 2H, Ar), 7.45 (d, 1H, J Hz, Hα), (m, 5H, Ph-H), 7.76 (d, 1H, J Hz, Hβ), 8.01 (d, 2H, J 8.21 Hz, Ph-H); 13 C NMR (100 MHz, CDCl 3 ) d (d, 2C, J 2 CF Hz, Ph-F), , , , , (d, 2C, J Hz, Ph-F), (d, 1C, CF J4 CF 3.32 Hz, Ph-F), , , , (d, 1C, J Hz, Ph-F), ; GC-MS m/z, observed: [M + 1], ; C H FO CF [M]+ requires: Figure S9. Mass spectrum of compound 3c.
6 S6 J. Braz. Chem. Soc. Figure S10. FTIR (KBr) spectrum of compound 3c. Figure S11. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 3c.
7 Vol. 26, No. 6, 2015 Ritter et al. S7 Figure S C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 3b. (E)-3-(4-Bromophenyl)-1-phenylprop-2-en-1-one (3d) mp C; IR (KBr) n max / cm , , , , , , , , , ; 1 H NMR (400 MHz, CDCl 3 ) d (m, 7H, Ph-H), 7.47 (d, 1H, J Hz, Hα), 7.69 (d, 1H, J Hz, Hβ), (m, 2H, Ph-H); 13 C NMR (100 MHz, CDCl 3 ) d , , , , , , , , , , ; GC-MS m/z, observed: [M+2], ; C 15 H 11 BrO [M] + requires: Figure S13. Mass spectrum of compound 3d.
8 S8 J. Braz. Chem. Soc. Figure S14. FTIR (KBr) spectrum of compound 3d. Figure S15. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 3d.
9 Vol. 26, No. 6, 2015 Ritter et al. S9 Figure S C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 3d. (E)-3-(4-Chlorophenyl)-1-phenylprop-2-en-1-one (3e) mp C; IR (KBr) n max / cm , , , , , , , , , , ; 1 H NMR (400 MHz, CDCl 3 ) d 7.34 (d, 2H, J 8.48 Hz, Ph-H), (m, 5H, Ph-H), d 7.46 (d, 1H, J Hz, Hα), 7.71 (d, 1H, J Hz, Hβ), 7.98 (d, 2H, J 7.15 Hz, Ph-H); 13 C NMR (100 MHz, CDCl 3 ) d , , , , , , , , , , ; GC-MS m/z, observed: [M + 1], ; C 15 H 11 ClO [M] + requires: Figure S17. Mass spectrum of compound 3e.
10 S10 J. Braz. Chem. Soc. Figure S18. FTIR (KBr) spectrum of compound 3e. Figure S19. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 3e.
11 Vol. 26, No. 6, 2015 Ritter et al. S11 Figure S C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 3e. (E)-1-Phenyl-3-p-tolylprop-2-en-1-one (3f) mp C; IR (KBr) n max / cm , , , , , , , , , 816,59, ; 1 H NMR (400 MHz, CDCl 3 ) d 2.36 (s, 3H, CH 3 ), 7.19 (d, 2H, J 7.95 Hz, Ph-H), 7.47 (d, 1H, J Hz, Hα), (m, 5H, Ph-H), 7.78 (d, 1H, J Hz, Hβ), 8.00 (d, 2H, J 7.04 Hz, Ph-H); 13 C NMR (100 MHz, CDCl 3 ) d 21.41, , , , 128,47, , , , , , , ; GC-MS m/z, observed: ; C 16 H 14 O [M] + requires: Figure S21. Mass spectrum of compound 3f.
12 S12 J. Braz. Chem. Soc. Figure S22. FTIR (KBr) spectrum of compound 3f. Figure S23. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 3f.
13 Vol. 26, No. 6, 2015 Ritter et al. S13 Figure S C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 3f. (E)-3-(3-Methoxyphenyl)-1-phenylprop-2-en-1-one (3g) mp C; IR (KBr) n max / cm , , , , , , , , , , , ; 1 H NMR (400 MHz, CDCl 3 ) d 3.81 (s, 3H, CH 3 ), (m, 1H, Ph-H), (m, 1H, Ph-H), (m, 1H, Ph-H), 7.30 (t, 1H, Ph-H), (m, 3H, Ph-H), 7.48 (d, 1H, J Hz, Hα), 7.74 (d, 1H, J Hz, Hβ), 7.99 (d, 2H, J 7.02 Hz, Ph-H); 13 C NMR (100 MHz, CDCl 3 ) d 55.19, , , , , , , , , , , , , , ; GC-MS m/z, observed: ; C 16 H 14 O 2 [M] + requires: Figure S25. Mass spectrum of compound 3g.
14 S14 J. Braz. Chem. Soc. Figure S26. FTIR (KBr) spectrum of compound 3g. Figure S27. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 3g.
15 Vol. 26, No. 6, 2015 Ritter et al. S15 Figure S C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 3g. (E)-3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one (3h) mp C; IR (KBr) n max / cm , , , , , , , , , , , ; 1 H NMR (400 MHz, CDCl 3 ) d (m, 1H, Ph-H), d (m, 3H, Ph-H), d 7.40 (d, 1H, J Hz, Hα), (m, 3H, Ph-H), 7.82 (d, 1H, J Hz, Hβ), (m, 1H, Ph-H); 13 C NMR (100 MHz, CDCl 3 ) d , , , , , , , , , , ; GC-MS m/z, observed: ; C 13 H 10 OS [M] + requires: Figure S29. Mass spectrum of compound 3h.
16 S16 J. Braz. Chem. Soc. Figure S30. FTIR (KBr) spectrum of compound 3h. Figure S31. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 3h.
17 Vol. 26, No. 6, 2015 Ritter et al. S17 Figure S C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 3h. (E)-3-(4-Methoxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one (3i) mp C; IR (KBr) n max / cm , , , , , , , , , , ; 1 H NMR (400 MHz, CDCl 3 ) d 3.81 (s, 3H, CH 3 ), (m, 2H, Ph-H), (m, 1H, Ph-H), 7.23 (d, 1H, J Hz, Hα), (m, 3H, Ph-H), 7.79 (d, 1H, J Hz, Hβ), (m, 1H, Ph-H); 13 C NMR (100 MHz, CDCl 3 ) d 55.33, , , , , , , , , , , , ; GC-MS m/z, observed: ; C 14 H 12 O 2 S [M] + requires: Figure S33. Mass spectrum of compound 3i.
18 S18 J. Braz. Chem. Soc. Figure S34. FTIR (KBr) spectrum of compound 3i. Figure S35. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 3i.
19 Vol. 26, No. 6, 2015 Ritter et al. S19 Figure S C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 3i. (E)-3-(4-Fluorophenyl)-1-(thiophen-2-yl)prop-2-en-1-one (3j) mp C; IR (KBr) n max / cm , , , , , , , , , , , ; 1 H NMR (400 MHz, CDCl 3 ) d (m, 2H, Ph-H), (m, 1H, Ph-H), 7.31 (d, 1H, J Hz, Hα), (m, 3H, Ph-H), 7.76 (d, 1H, J Hz, Hβ), (m, 1H, Ph-H); 13 C NMR (100 MHz, CDCl 3 ) d (d, 2C, J Hz, Ph-F), (d, 1C, CF J4 CF 2.45 Hz, Ph-F), , , , , , (d, 2C, J Hz, Ph-F), , , (d, 1C, C-F J1 C-F Hz, Ph-F), , ; GC-MS m/z, observed: ; C 13 H 9 FOS [M] + requires: Figure S37. Mass spectrum of compound 3j.
20 S20 J. Braz. Chem. Soc. Figure S38. FTIR (KBr) spectrum of compound 3j. Figure S39. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 3j.
21 Vol. 26, No. 6, 2015 Ritter et al. S21 Figure S C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 3j. (E)-3-(4-Bromophenyl)-1-(thiophen-2-yl)prop-2-en-1-one (3k) mp C; IR (KBr) n max / cm , , , , , , , , , , , ; 1 H NMR (400 MHz, CDCl 3 ) d (m, 1H, Ph-H), 7.35 (d, 1H, J Hz, Hα), (m, 4H, Ph-H), (m, 1H, Ph-H), 7.71 (d, 1H, J Hz, Hβ), (m, 1H, Ph-H); 13 C NMR (100 MHz, CDCl 3 ) d , , , , , , , , , , ; GC-MS m/z, observed: [M+2], ; C 13 H 9 BrOS [M]+ requires: Figure S41. Mass spectrum of compound 3k.
22 S22 J. Braz. Chem. Soc. Figure S42. FTIR (KBr) spectrum of compound 3k. Figure S43. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 3k.
23 Vol. 26, No. 6, 2015 Ritter et al. S23 Figure S C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 3k. (E)-3-(4-Chlorophenyl)-1-(thiophen-2-yl)prop-2-en-1-one (3l) mp C; IR (KBr) n max / cm , , , , , , , , , , , , ; 1 H NMR (400 MHz; CDCl 3 ) d (m, 1H, Ph-H), (m, 2H, Ph-H), 7.34 (d, 1H, J Hz, Hα), (m, 3H, Ph-H), 7.72 (d, 1H, J Hz, Hβ), 7.82 (m, 1H, Ph-H); 13 C NMR (100 MHz, CDCl 3 ) d , , , , , , , , , , ; GC-MS m/z, observed: [M+1], ; C 13 H 9 ClOS [M] + requires: Figure S45. Mass spectrum of compound 3l.
24 S24 J. Braz. Chem. Soc. Figure S46. FTIR (KBr) spectrum of compound 3l. Figure S47. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 3l.
25 Vol. 26, No. 6, 2015 Ritter et al. S25 Figure S C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 3l. (E)-1-(Thiophen-2-yl)-3-p-tolylprop-2-en-1-one (3m) mp C; IR (KBr) n max / cm , , , , , , , , ; 1 H NMR (400 MHz, CDCl 3 ) d 2.34 (s, 3H, CH 3 ), 7.13 (t, 1H, Ph-H), 7.18 (d, 2H, J 7.91 Hz, Ph-H), 7.35 (d, 1H, J Hz, Hα), 7.50 (d, 2H, J 8.04 Hz, Ph-H), 7.62 (d, 1H, J 4.95 Hz, Ph-H), 7.80 (d, 1H, J Hz, Hβ), 7.82 (d, 1H, J 4.19 Hz, Ph-H); 13 C NMR (100 MHz; CDCl 3 ) d 21.38, , , , , , , , , , , ; GC-MS m/z, observed: ; C 14 H 12 OS [M] + requires: Figure S49. Mass spectrum of compound 3m.
26 S26 J. Braz. Chem. Soc. Figure S50. FTIR (KBr) spectrum of compound 3m. Figure S51. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 3m.
27 Vol. 26, No. 6, 2015 Ritter et al. S27 Figure S C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 3m. (E)-3-(3-Methoxyphenyl)-1-(thiophen-2-yl) prop-2-en-1-one (3n) mp C; IR (KBr) n max / cm , , , , , , , , , , , , , ; 1 H NMR (400 MHz, CDCl 3 ) d 3.81 (s, 3H, CH 3 ), (m, 1H, Ph-H), (m, 2H, Ph-H), 7.19 (d, J 7.53 Hz, 1H, Ph-H), 7.29 (t, 1H, Ph-H), 7.36 (d, 1H, J Hz, Hα), (m, 1H, Ph-H), 7.77 (d, 1H, J Hz, Hβ), (m, 1H, Ph-H); 13 C NMR (100 MHz, CDCl 3 ) d 55.20, , , , , , , , , , , , , ; GC-MS m/z, observed: ; C 14 H 12 O 2 S [M] + requires: Figure S53. Mass spectrum of compound 3n.
28 S28 J. Braz. Chem. Soc. Figure S54. FTIR (KBr) spectrum of compound 3n. Figure S55. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 3n.
29 Vol. 26, No. 6, 2015 Ritter et al. S29 Figure S C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 3n.
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