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Supplementary Information
Anti-Parasite and Cytotoxic Activities of Chloro and Bromo L-Tyrosine Derivatives
Manuel Pastrana Restrepo,a Elkin Galeano Jaramillo,*
,a Alejandro Martínez Martínez,
a
Ana Mesa Arangob and Sara Robledo Restrepo
c
aProductos Naturales Marinos, Departamento de Farmacia,
Facultad de Ciencias Farmacéuticas y Alimentarias, Universidad de Antioquia (UdeA),
Calle 70 No. 52-21, Laboratorio 2-131, 050010 Medellín, Colombia
bGrupo de Investigación Dermatológica, Facultad de Medicina, Universidad de Antioquia (UdeA),
050010 Medellín, Colombia
cPrograma de Estudio y Control de Enfermedades Tropicales (PECET),
Facultad de Medicina, Universidad de Antioquia (UdeA), Calle 62 No. 52-59,
Laboratorio 632, 050010 Medellín, Colombia
Figure S1. 1H NMR spectra (300 MHz, CDCl3) of Int1, methyl (S)-3-(3-bromo-4-hydroxyphenyl)-
2-((tert-butoxycarbonyl)-amino)-propanoate.
______________________________
*e-mail: [email protected]
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Figure S2. 1H NMR spectra (300 MHz, CDCl3) of Int2, methyl (S)-2-((tert butoxycarbonyl)-amino)-
3-(3,5-dibromo-4-hydroxyphenyl)-propanoate.
Figure S3. 1H NMR spectra (300 MHz, CDCl3) of Int3, methyl (S)-3-(3-chloro-4-hydroxyphenyl)-
2-((tert-butoxycarbonyl)-amino)-propanoate.
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Figure S4. 1H NMR spectra (300 MHz, CDCl3) of Int4, methyl (S)-2-((tert-butoxycarbonyl)-amino)-
3-(3,5-dichloro-4-hydroxyphenyl)-propanoate.
Figure S5. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 4, (S)-2-amino-3-(3-bromo-
4-hydroxyphenyl)-propanoic acid.
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Figure S6. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 4, (S)-2-amino-3-(3-bromo-
4-hydroxyphenyl)-propanoic acid.
Figure S7. ESI-Q-Tof-HRMS of compound 4, (S)-2-amino-3-(3-bromo-4-hydroxyphenyl)-propanoic acid.
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Figure S8. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 5, (S)-2-amino-3-(3,5-dibromo-
4-hydroxyphenyl)-propanoic acid.
Figure S9. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 5, (S)-2-amino-3-(3,5-dibromo-
4-hydroxyphenyl)-propanoic acid.
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Figure S10. ESI-Q-Tof-HRMS of compound 5, (S)-2-amino-3-(3,5-dibromo-4-hydroxyphenyl)-propanoic
acid.
Figure S11. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 6, (S)-2-amino-3-(3-chloro-
4-hydroxyphenyl)-propanoic acid.
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Figure S12. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 6, (S)-2-amino-3-(3-chloro-
4-hydroxyphenyl)-propanoic acid.
Figure S13. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 7, (S)-2-amino-3-(3,5-dichloro-
4-hydroxyphenyl)-propanoic acid.
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Figure S14. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 7, (S)-2-amino-3-(3,5-dichloro-
4-hydroxyphenyl)-propanoic acid.
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Figure S15. ESI-Q-Tof-HRMS of compound 7, (S)-2-amino-3-(3,5-dichloro-4-hydroxyphenyl)-propanoic
acid.
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Figure S16. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 8, (S)-2-amino-3-(3-bromo-
4-methoxyphenyl)-propanoic acid.
Figure S17. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 8, (S)-2-amino-3-(3-bromo-
4-methoxyphenyl)-propanoic acid.
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Figure S18. ESI-Q-Tof-HRMS of compound 8, (S)-2-amino-3-(3-bromo-4 methoxyphenyl)-propanoic acid.
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Figure S19. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 9, (S)-2-amino-3-(3,5-dibromo-
4-methoxyphenyl)-propanoic acid.
Figure S20. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 9, (S)-2-amino-3-(3,5-dibromo-
4-methoxyphenyl)-propanoic acid.
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Figure S21. ESI-Q-Tof-HRMS of compound 9, (S)-2-amino-3-(3,5-dibromo-4-methoxyphenyl)-propanoic
acid.
Figure S22. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 10, (S)-2-amino-3-(3-chloro-
4-methoxyphenyl)-propanoic acid.
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Figure S23. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 10, (S)-2-amino-3-(3-chloro-
4-methoxyphenyl)-propanoic acid.
Figure S24. ESI-Q-Tof-HRMS of compound 10, (S)-2-amino-3-(3-chloro-4 methoxyphenyl)-propanoic acid.
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Figure S25. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 11, (S)-2-amino-3-(3,5-dichloro-
4-methoxyphenyl)-propanoic acid.
Figure S26. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 11, (S)-2-amino-3-(3,5-dichloro-
4-methoxyphenyl)-propanoic acid.
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Figure S27. ESI-Q-Tof-HRMS of compound 11, (S)-2-amino-3-(3,5-dichloro-4-methoxyphenyl)-propanoic
acid.
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Figure S28. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 12, (S)-3-(3-bromo-
4-hydroxyphenyl)-2-(dimethylamino)-propanoic acid.
Figure S29. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 12, (S)-3-(3-bromo-
4-hydroxyphenyl)-2-(dimethylamino)-propanoic acid.
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Figure S30. ESI-Q-Tof-HRMS of compound 12, (S)-3-(3-bromo-4-hydroxyphenyl)-2-(dimethylamino)-
propanoic acid.
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Figure S31. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 13, (S)-3-(3-chloro-
4-hydroxyphenyl)-2-(dimethylamino)-propanoic acid.
Figure S32. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 13, (S)-3-(3-chloro-
4-hydroxyphenyl)-2-(dimethylamino)-propanoic acid.
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Figure S33. ESI-Q-Tof-HRMS of compound 13, (S)-3-(3-chloro-4-hydroxyphenyl)-2-(dimethylamino)-
propanoic acid.
Figure S34. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 14, (S)-3-(3,5-dichloro-
4-hydroxyphenyl)-2-(dimethylamino)-propanoic acid.
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Figure S35. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 14, (S)-3-(3,5-dichloro-
4-hydroxyphenyl)-2-(dimethylamino)-propanoic acid.
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Figure S36. ESI-Q-Tof-HRMS of compound 14, (S)-3-(3,5-dichloro-4-hydroxyphenyl)-2-(dimethylamino)-
propanoic acid.
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Figure S37. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 15, (S)-3-(3-bromo-
4-methoxyphenyl)-2-(dimethylamino)-propanoic acid.
Figure S38. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 15, (S)-3-(3-bromo-
4-methoxyphenyl)-2-(dimethylamino)-propanoic acid.
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Figure S39. ESI-Q-Tof-HRMS of compound 15, (S)-3-(3-bromo-4-methoxyphenyl)-2-(dimethylamino)-
propanoic acid.
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Figure S40. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 16, (S)-3-(3,5-dibromo-
4-methoxyphenyl)-2-(dimethylamino)-propanoic acid.
Figure S41. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 16, (S)-3-(3,5-dibromo-
4-methoxyphenyl)-2-(dimethylamino)-propanoic acid.
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Figure S42. ESI-Q-Tof-HRMS of compound 16, (S)-3-(3,5-dibromo-4-methoxyphenyl)-2-(dimethylamino)-
propanoic acid.
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Figure S43. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 17, (S)-3-(3-chloro-
4-methoxyphenyl)-2-(dimethylamino)-propanoic acid.
Figure S44. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 17, (S)-3-(3-chloro-
4-methoxyphenyl)-2-(dimethylamino)-propanoic acid.
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Figure S45. ESI-Q-Tof-HRMS of compound 17, (S)-3-(3-chloro-4-methoxyphenyl)-2-(dimethylamino)-
propanoic acid.
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Figure S46. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 18, (S)-3-(3,5-dichloro-
4-methoxyphenyl)-2-(dimethylamino)-propanoic acid.
Figure S47. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 18, (S)-3-(3,5-dichloro-
4-methoxyphenyl)-2-(dimethylamino)-propanoic acid.
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Figure S48. ESI-Q-Tof-HRMS of compound 18, (S)-3-(3,5-dichloro-4-methoxyphenyl)-2-(dimethylamino)-
propanoic acid.
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Figure S49. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 19, (S)-1-carboxy-2-(3-chloro-
4-hydroxyphenyl)-N,N,N-trimethylethan-1-aminium.
Figure S50. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 19, (S)-1-carboxy-2-(3-chloro-
4-hydroxyphenyl)-N,N,N-trimethylethan-1-aminium.
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Figure S51. ESI-Q-Tof-HRMS of compound 19, (S)-1-carboxy-2-(3-chloro-4-hydroxyphenyl)-
N,N,N-trimethylethan-1-aminium
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Figure S52. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 20, (S)-1-carboxy-2-(3,5-dichloro-
4-hydroxyphenyl)-N,N,N-trimethylethan-1-aminium.
Figure S53. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 20, (S)-1-carboxy-2-(3,5-dichloro-
4-hydroxyphenyl)-N,N,N-trimethylethan-1-aminium.
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Figure S54. ESI-Q-Tof-HRMS of compound 20, (S)-1-carboxy-2-(3,5-dichloro-4-hydroxyphenyl)-
N,N,N-trimethylethan-1-aminium.
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Figure S55. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 21, (S)-2-(3-bromo-
4-methoxyphenyl)-1-carboxy-N,N,N-trimethylethan-1-aminium.
Figure S56. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 21, (S)-2-(3-bromo-
4-methoxyphenyl)-1-carboxy-N,N,N-trimethylethan-1-aminium.
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Figure S57. ESI-Q-Tof-HRMS of compound 21, (S)-2-(3-bromo-4-methoxyphenyl)-1-carboxy-
N,N,N-trimethylethan-1-aminium.
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Figure S58. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 22, (S)-1-carboxy-2-(3,5-dibromo-
4-methoxyphenyl)-N,N,N-trimethylethan-1-aminium.
Figure S59. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 22, (S)-1-carboxy-2-(3,5-dibromo-
4-methoxyphenyl)-N,N,N-trimethylethan-1-aminium.
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Figure S60. ESI-Q-Tof-HRMS of compound 22, (S)-1-carboxy-2-(3,5-dibromo-4-methoxyphenyl)-
N,N,N-trimethylethan-1-aminium.
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Figure S61. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 23, (S)-2-(3-chloro-
4-methoxyphenyl)-1-carboxy-N,N,N-trimethylethan-1-aminium.
Figure S62. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 23, (S)-2-(3-chloro-
4-methoxyphenyl)-1-carboxy-N,N,N-trimethylethan-1-aminium.
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Figure S63. ESI-Q-Tof-HRMS of compound 23, (S)-2-(3-chloro-4-methoxyphenyl)-1-carboxy-
N,N,N-trimethylethan-1-aminium.
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Figure S64. 1H NMR spectra (300 MHz, D2O, DMSO-d6) of compound 24, (S)-1-carboxy-2-(3,5-dichloro-
4-methoxyphenyl)-N,N,N-trimethylethan-1-aminium.
Figure S65. 13
C NMR spectra (75 MHz, D2O, DMSO-d6) of compound 24, (S)-1-carboxy-2-(3,5-dichloro-
4-methoxyphenyl)-N,N,N-trimethylethan-1-aminium.
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Figure S66. ESI-Q-Tof-HRMS of compound 24, (S)-1-carboxy-2-(3,5-dichloro-4-methoxyphenyl)-
N,N,N-trimethylethan-1-aminium.
