Molecules 2018, 23, 774; doi:10.3390/molecules23040774 www.mdpi.com/journal/molecules Supplementary Materials
In vitro Anti-Toxoplasma gondii and Antimicrobial Activity of Amides Derivated From Cinnamic Acid
Graziela Rangel Silveira1,*, Karoline Azerêdo Campelo1, Gleice Rangel Silveira Lima1, Lais Pessanha Carvalho2, Solange Silva Samarão3, Olney Vieira-da-Motta3, Leda Mathias1, Carlos
Roberto Ribeiro Matos1, Ivo José Curcino Vieira1, Edesio José Tenório de Melo2, Edmilson José Maria1
1 Laboratório de Ciências Químicas, Centro de Ciências e Tecnologia, Universidade Estadual do Norte Fluminense-Darcy Ribeiro, Av. Alberto Lamego, 2000 - Parque Califórnia, Campos dos Goytacazes/RJ, 28013-602, Brasil; graziela_sil@hotmail.com (G. R. S.); karolcampelo16@yahoo.com.br (K. A. C.);
gleice.sil@hotmail.com (G. R. S. L.); leddam8@gmail.com (L. M.); matos@uenf.br (C. R. R. M.);
curcino@uenf.br (I. J. C. V.); edmilson_maria@yahoo.com.br (E. J. M.).
2 Laboratório de Biologia Celular e Tecidual, Centro de Biociências e Biotecnologia, Universidade Estadual do Norte Fluminense-Darcy Ribeiro, Av. Alberto Lamego, 2000 - Parque Califórnia, Campos dos Goytacazes/RJ,28013-602, Brasil; lais_pessanha@hotmail.com (L. P. C.); ejtm1202@gmail.com (E. J. T. M.).
3 Laboratório de Sanidade Animal, Centro de Ciências e Tecnologias Agropecuárias, Universidade Estadual do Norte Fluminense-Darcy Ribeiro, Av. Alberto Lamego, 2000 - Parque Califórnia, Campos dos Goytacazes/RJ, 28013-602, Brasil; solangesamarao@gmail.com (S. S. S.); olney.motta@gmail.com (O.
V.dM.).
* Corresponding author: graziela_sil@hotmail.com; Tel.: +55-022-2728-6167
Figure S1. 1H NMR spectrum of compound 1 (CDCl3, 500 MHz).
Figure S2. 13C NMR spectrum of compound 1 (CDCl3, 125 MHz).
Figure S3. HMBC spectrum of compound 1 (CDCl3, 500 MHz).
001 HSQC.ESP
8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5
F2 Chemical Shif t (ppm)
-10 0 10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210
F1 Chemical Shift (ppm)
Figure S4. HSQC spectrum of compound 1 (CDCl3, 500 MHz).
40 60 80 100 120 140 160 180 200 220 240 260 280 300 320 340 0
200000 400000 600000 800000 1000000 1200000 1400000 1600000 1800000 2000000 2200000 2400000 2600000 2800000 3000000 3200000
m /z-->
Abundance
Scan 1852 (21.348 m in): 001.D \data.m s (-1834) (-) 134.0
103.0 77.0
51.0 160.1180.9 207.0230.1252.9 281.0 314.9 341.0
Figure S5. Mass spectrum of compound 1 (CH2Cl2).
Figure S6. IR spectrum (KBr) of compound 1.
Figure S7. 1H NMR spectrum of compound 2 (CDCl3, 500 MHz).
Figure S8. 13C NMR spectrum of compound 2 (CDCl3, 125 MHz).
Figure S9. HMBC spectrum of compound 2 (CDCl3, 500 MHz).
002 HSQC.ESP
8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5
F2 Chemical Shif t (ppm)
-10 0 10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210
F1 Chemical Shift (ppm)
Figure S10. HSQC spectrum of compound 2 (CDCl3, 500 MHz).
40 60 80 100 120 140 160 180 200 220 240 260 280 300 320 340 0
500000 1000000 1500000 2000000 2500000 3000000 3500000 4000000 4500000 5000000 5500000 6000000
m /z-->
Abundance
Scan 1694 (19.854 m in): 002.D \data.m s 131.1
103.1
77.0
265.1
51.0 160.0
207.0 236.0 315.0 341.0
186.0 292.9
Figure S11. Mass spectrum of compound 2 (CH2Cl2).
Figure S12. IR spectrum (KBr) of compound 2.
Figure 13. 1H NMR spectrum of compound 3 (CDCl3, 500 MHz).
Figure S14. 13C NMR spectrum of compound 3 (CDCl3, 125 MHz).
Figure S15. HMBC spectrum of compound 3 (CDCl3, 500 MHz).
003 HSQC.ESP
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5
F2 Chemical Shif t (ppm)
0 10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180
F1 Chemical Shift (ppm)
Figure S16 HSQC spectrum of compound 3 (CDCl3, 500 MHz).
40 60 80 100 120 140 160 180 200 220 240 260 280 300 320 340 0
500000 1000000 1500000 2000000 2500000 3000000 3500000 4000000 4500000
m/z-->
Abundance
Scan 1817 (21.017 min):003.D\data.ms 131.1
103.0
77.0
160.0
285.1 51.0
207.0 253.0 341.0
181.0 229.0 315.0
Figure S17. Mass spectrum of compound 3 (CH2Cl2).
Figure S18. IR spectrum (KBr) of compound 3.
Figure S19. 1H NMR spectrum of compound 4 (CDCl3, 500 MHz).
Figure S20. 13C NMR spectrum of compound 4 (CDCl3, 125 MHz).
Figure S21. HMBC spectrum of compound 4 (CDCl3, 500 MHz).
004 HSQCED.ESP
12 11 10 9 8 7 6 5 4 3
F2 Chemical Shif t (ppm)
0 10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200
F1 Chemical Shift (ppm)
Figure S22. HSQC spectrum of compound 4 (CDCl3, 500 MHz).
60 80 100 120 140 160 180 200 220 240 260 280 300 320 340 0
500000 1000000 1500000 2000000 2500000 3000000 3500000 4000000 4500000 5000000
m/z-->
Abundance
Scan 2212 (24.752 min): 004.D\data.ms 131.1
103.0
77.0
160.0
296.1 51.0
207.0 253.0 341.0
181.0 232.1 317.0
Figure S23. Mass spectrum of compound 4 (CH2Cl2).
Figure S24. IR spectrum (KBr) of compound 4.
Figure S25. 1H NMR spectrum of compound 5 (CDCl3, 500 MHz).
Figure S26. 13C NMR spectrum of compound 5 (CDCl3, 125 MHz).
Figure S27. HMBC spectrum of compound 5 (CDCl3, 500 MHz).
005 HSQC.ESP
8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0
F2 Chemical Shif t (ppm)
0 10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200
F1 Chemical Shift (ppm)
Figure S28. HSQC spectrum of compound 5 (CDCl3, 500 MHz).
50 100 150 200 250 300 350 400 450 500 550 600 0
500000 1000000 1500000 2000000 2500000 3000000 3500000 4000000 4500000 5000000 5500000 6000000
m /z-->
Abundance
Scan 2047 (23.192 m in): 006.D \data.m s 164.1
103.0
311.1
51.0 207.0 253.0 355.0 429.1 503.1 553.1 627.1
Figure S29. Mass spectrum of compound 5 (CH2Cl2).
Figure S30. IR spectrum (KBr) of compound 5.
Figure S31. 1H NMR spectrum of compound 6 (CDCl3, 500 MHz).
Figure S32. 13C NMR spectrum of compound 6 (CDCl3, 125 MHz).
Figure S33. HMBC spectrum of compound 6 (CDCl3, 500 MHz).
006 HSQC.ESP
10 9 8 7 6 5 4 3
F2 Chemical Shif t (ppm)
-10 0 10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210
F1 Chemical Shift (ppm)
Figure S34. HSQC spectrum of compound 6 (CDCl3, 500 MHz).
4 0 6 0 8 0 1 0 0 1 2 0 1 4 0 1 6 0 1 8 0 2 0 0 2 2 0 2 4 0 2 6 0 2 8 0 3 0 0 3 2 0 3 4 0 3 6 0 3 8 0 4 0 0 4 2 0 4 4 0 0
5 0 0 0 0 1 0 0 0 0 0 1 5 0 0 0 0 2 0 0 0 0 0 2 5 0 0 0 0 3 0 0 0 0 0 3 5 0 0 0 0 4 0 0 0 0 0 4 5 0 0 0 0 5 0 0 0 0 0
m / z -->
A b u n d a n c e
S c a n 2 9 3 6 (3 1 .5 9 8 m in ): 0 0 9 .D \ d a ta .m s (-2 8 3 7 ) (-) 1 7 5 .9
1 0 2 .0
1 3 0 .1
6 3 .0 2 0 5 .0
3 7 4 .0
2 5 3 .0 2 8 1 .0 3 3 1 .1 4 0 6 .1 4 5 2 .1
Figure S35. Mass spectrum of compound 6 (CH2Cl2).
Figure S36. IR spectrum (KBr) of compound 6.
Figure S37. 1H NMR spectrum of compound 7 (CDCl3, 500 MHz).
Figure S38. 13C NMR spectrum of compound 7 (CDCl3, 125 MHz).
Figure S39. HMBC spectrum of compound 7 (CDCl3, 500 MHz).
007 HSQC.ESP
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0
F2 Chemical Shif t (ppm)
-10 0 10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210
F1 Chemical Shift (ppm)
Figure S40. HSQC spectrum of compound 7 (CDCl3, 500 MHz).
4 0 6 0 8 0 1 0 0 1 2 0 1 4 0 1 6 0 1 8 0 2 0 0 2 2 0 2 4 0 2 6 0 2 8 0 3 0 0 3 2 0 3 4 0 3 6 0 3 8 0 4 0 0 4 2 0 4 4 0 0
5 0 0 0 0 1 0 0 0 0 0 1 5 0 0 0 0 2 0 0 0 0 0 2 5 0 0 0 0 3 0 0 0 0 0 3 5 0 0 0 0 4 0 0 0 0 0
m /z-->
A b u n d a n c e
S c a n 3 8 6 2 (4 0 .3 5 3 m in ): 0 1 0 .D \d a ta .m s (-3 9 4 9 ) (-) 1 7 6 .0
2 0 5 .1 1 0 2 .0
1 2 9 .9
3 4 1 .1 5 1 .0
3 1 1 .1
2 8 3 .1 4 0 5 .1
2 5 4 .0 3 7 3 .0 4 5 1 .0
Figure S41. Mass spectrum of compound 7 (CH2Cl2).
Figure S42. IR spectrum (KBr) of compound 7.
Figure S43. 1H NMR spectrum of compound 8 (CDCl3, 500 MHz).
Figure S44. 13C NMR spectrum of compound 8 (CDCl3, 125 MHz).
Figure S45. HMBC spectrum of compound 8 (CDCl3, 500 MHz).
117.200.001.2rr.esp
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5
F2 Chemical Shif t (ppm)
8 16 24 32 40 48 56 64 72 80 88 96 104 112 120 128 136 144 152 160 168 176
F1 Chemical Shift (ppm)
Figure S46. HSQC spectrum of compound 8 (CDCl3, 500 MHz).
50 100 150 200 250 300 350 400 450 500 550 0
500000 1000000 1500000 2000000 2500000 3000000 3500000 4000000 4500000 5000000
m /z-->
A bundance
S can 1971 (22.473 m in): 011.D \data.m s (-1947) (-) 138.0
77.0
367.0 183.0
240.0
330.0
287.1 405.1 467.1503.1 554.2
Figure S47. Mass spectrum of compound 8 (CH2Cl2).
Figure S48. IR spectrum (KBr) of compound 8.
