SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF TRIAZINE

96 Pages·2015·2.44 MB·English

Electronic Supplementary Material (ESI) for RSC Advances.
This journal is © The Royal Society of Chemistry 2016

SYNTHESIS ANDANTIMICROBIAL ACTIVITY OF TRIAZINE

DENDRIMERS WITH DABCO GROUPS

R. S. Sreeperumbuduru, Z.M. Abid, H.-H. Chen, S. M. McGillivray*, E. E. Simanek*
Departments of Chemistry and Biology, Texas Christian University, Fort Worth TX, 76129

1
Contributions

A majority of the synthesis work was accomplished by R.S.S. Z.M.A. contributed to the synthetic effort.
Both R.S.S. and Z.M.A. collected the biological data. Z.M.A. maintained the cell preparations. H.H.C.
contributed to the design of the study and one synthetic compound. S.M.G. supervised the biological
assays. E.E.S. supervised the synthetic efforts. R.S.S. and Z.M.A. assembled the manuscript. S.M.G. and
E.E.S. supervised communication of the efforts.

Table of Contents

General Experimental 5
Compound 1-Me
Experimental 6
SI Figure 1. 1H NMR spectrum of 1-Me 7
SI Figure 2. 13C NMR spectrum of 1-Me 8
Compound 1-Bz
Experimental 9
SI Figure 3. 1H NMR spectrum of 1-Bz 10
SI Figure 4. 13C NMR spectrum of 1-Bz 11
Compound 1-C
12
Experimental 12
SI Figure 5. 1H NMR spectrum of 1-C 13
12
SI Figure 6. 13C NMR spectrum of 1-C 14
12
Compound 1-Me
2
Experimental 15
SI Figure 7. 1H NMR spectrum of 1-Me 16
2
SI Figure 8. 13C NMR spectrum of 1-Me 17
2
Compound 1-Bz
2
Experimental 18
SI Figure 9. 1H NMR spectrum of 1-Bz 19
2
SI Figure 10. 13C NMR spectrum of 1-Bz 20
2
Compound 1-(C )
12 2
Experimental 21
SI Figure 11. 1H NMR spectrum of 1-(C ) 22
12 2
SI Figure 12. 13C NMR spectrum of 1-(C ) 23
12 2
Compound 8a
Experimental 24
SI Figure 13. 1H NMR spectrum of 8a 25
SI Figure 14. 13C NMR spectrum of 8a 26
SI Figure 15. Mass Spectra spectrum of 8a 27
Compound 8c
Experimental 28
SI Figure 16. 1H NMR spectrum of 8c 29
SI Figure 17. 13C NMR spectrum of 8c 30
SI Figure 18. Mass Spectra spectrum of 8c 31
Compound 2-Me
Experimental 32
SI Figure 19. 1H NMR spectrum of 2-Me 33
SI Figure 20. 13C NMR spectrum of 2-Me 34
2
Compound 2-Bz
Experimental 35
SI Figure 21. 1H NMR spectrum of 2-Bz 36
SI Figure 22. 13C NMR spectrum of 2-Bz 37
Compound 2-C
12
Experimental 38
SI Figure 23. 1H NMR spectrum of 2-C 39
12
SI Figure 24. 13C NMR spectrum of 2-C 40
12
Compound 9a
Experimental 41
SI Figure 25. 1H NMR spectrum of 9a 42
SI Figure 26. 13C NMR spectrum of 9a 43
SI Figure 27. Mass Spectra spectrum of 9a 44
Compound 9c
Experimental 45
SI Figure 28. 1H NMR spectrum of 9c 46
SI Figure 29. 13C NMR spectrum of 9c 47
SI Figure 30. Mass Spectra spectrum of 9c 48
Compound 3-Me
Experimental 49
SI Figure 31. 1H NMR spectrum of 3-Me 50
SI Figure 32. 13C NMR spectrum of 3-Me 51
Compound 3-Bz
Experimental 52
SI Figure 33. 1H NMR spectrum of 3-Bz 53
SI Figure 34. 13C NMR spectrum of 3-Bz 54
Compound 3-C
12
Experimental 55
SI Figure 35. 1H NMR spectrum of 3-C 56
12
SI Figure 36. 13C NMR spectrum of 3-C 57
12
Compound 10a
Experimental 58
SI Figure 37. 1H NMR spectrum of 10a 59
SI Figure 38. 13C NMR spectrum of 10a 60
SI Figure 39. Mass spectra spectrum of 10a 61
Compound 10c
Experimental 62
SI Figure 40. 1H NMR spectrum of 10c 63
SI Figure 41. 13C NMR spectrum of 10c 64
SI Figure 42. Mass spectra spectrum of 10c 65
Compound 4-Me
Experimental 66
SI Figure 43. 1H NMR spectrum of 4-Me 67
SI Figure 44. 13C NMR spectrum of 4-Me 68
Compound 4-Bz
Experimental 69
SI Figure 45. 1H NMR spectrum of 4-Bz 70
SI Figure 46. 13C NMR spectrum of 4-Bz 71
Compound 4-C
12
Experimental 72
SI Figure 47. 1H NMR spectrum of 4-C 73
12
3
SI Figure 48. 13C NMR spectrum of 4-C 74
12
Compound 11a
Experimental 75
SI Figure 49. 1H NMR spectrum of 11a 76
SI Figure 50. 13C NMR spectrum of 11a 77
SI Figure 51. Mass Spectra spectrum of 11a 78
Compound 11c
Experimental 79
SI Figure 52. 1H NMR spectrum of 11c 80
SI Figure 53. 13C NMR spectrum of 11c 81
SI Figure 54. Mass Spectra spectrum of 11c 82
Compound 6-Me
Experimental 83
SI Figure 55. 1H NMR spectrum of 6-Me 84
SI Figure 56. 13C NMR spectrum of 6-Me 85
Compound 6-Bz
Experimental 86
SI Figure 57. 1H NMR spectrum of 6-Bz 87
SI Figure 58. 13C NMR spectrum of 6-Bz 88
Compound 6-C
12
Experimental 89
SI Figure 59. 1H NMR spectrum of 6-C 90
12
SI Figure 60. 13C NMR spectrum of 6-C 91
12

MIC ASSAY- Graphical Representation 92-96

4
General Experimental
Microwave: A CEM SP Discovery microwave was utilized for these experiments. Reactions
were performed in dynamic mode wherein microwave power is modulated to maintain the set point
temperature.
Automated Chromatography: A Combiflash RF Automated Chromatographer (Teledyne
ISCO) was used for these experiments. All the purifications were performed using a solid loading
method.

5
Compound 1-Me:
Methyl iodide (0.5 ml, 8.9 mmol) was added slowly to a solution of DABCO (1 g, 8.9 mmol) in
hexane (25 ml) at 0oC and stirred for 1 hr at room temperature. The solvent was evaporated, and
residue was washed with hexanes (100 ml) and dried to yield a pale yellow solid (1.02 g, 90%).
1H NMR (400 MHz, CD OD) δ 3.50 (t,  6H,  DABCO),  δ 3.25 (t,  6H,  DABCO),  δ 3.15 (t, 3H, -
3
CH ); 13C NMR (100 MHz, D O) 54.0, 44.3 (DABCO), 51.7 (-CH ).
3 2 3

6
SI Figure 1. 1H NMR spectrum of 1-Me

7
SI Figure 2. 13C NMR spectrum of compound 1-Me

8
Compound 1-Bz:

Benzyl Chloride (5.13 ml, 44.6 mmol) is added slowly to the solution of DABCO (5.03 g, 44.6
mmol) in THF (50 ml) at room temperature and a white precipitate is formed after 10 min. The
solvent was evaporated and the precipitate was washed with ethyl acetate and hexane and dried
to yield a white solid (10.25 g, 96.24%). 1H NMR (400 MHz, DMSO) δ 7.52 (C H ), δ 4.63
6 5
(C H -CH ), δ 3.40 (t,  6H,  DABCO),  δ 3.01 (t, 6H, DABCO); 13C NMR (100 MHz, D O) 133.0,
6 5 2 2
130.8, 129.2, 126.0 (C H -), 68.3 (C H -CH ), 51.9, 44.2 (DABCO).
6 5 6 5 2

9
SI Figure 3. 1H NMR spectrum of compound 1-Bz

10