Efficient microwave-assisted synthetic protocols and in silico behaviour prediction of per-substituted β-cyclodextrins.
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1 Efficient microwave-assisted synthetic protocols and in silico behaviour prediction of per-substituted β-cyclodextrins. K. Martina a, G. Cravotto a *, M. Caporaso a, L. Rinaldi a,b, C. Villalonga-Barber c and G. Ermondi b a Dipartimento di Scienza e Tecnologia del Farmaco, University of Turin, Via Pietro Giuria 9, Torino (Italy), Fax ; Tel: giancarlo.cravotto@unito.it. b Department of Molecular Biotechnology and Health Sciences, University of Torino, Via Nizza 52, Torino, c Institute of Biology, Medicinal Chemistry and Biotechnology, National Hellenic Research Foundation, 48. Vas. Constantinou Ave., Athens, Greece. Contents: Fig. 1: 1 H-NMR of per-(6-benzylamino-6-deoxy)-β-cd (2a) Fig. 2: 13 C-NMR of 2a Fig. 3: HMQC 1 H- 13 C spectrum of 2a Fig 4: MS (ESI) spectrum of 2a Fig. 5: 1 H-NMR of 2b Fig. 6: 13 C-NMR of per-(6-allylamino-6-deoxy)-β-cd (2b) Fig. 7: HMQC 1 H- 13 C spectrum of 2b Fig 8: MS (ESI) spectrum of 2b Fig. 9: 1 H-NMR of per-(6-butylamino-6-deoxy)-β-cd (2c) Fig. 10: 13 C-NMR of 2c Fig. 11: HMQC 1 H- 13 C spectrum of 2c Fig 12: MS (ESI) spectrum of 2c Fig. 13: 1 H-NMR of per-(6-anilino-6-deoxy)-β-cd (2d) Fig. 14: 13 C-NMR of 2d Fig. 15: HMQC 1 H- 13 C spectrum of 2d Fig 16: MS (ESI) spectrum of 2d Fig. 17: 1 H-NMR of per-(6-(2-chlorobenzylamino)-6-deoxy)-β-cd (2e) Fig. 18: 13 C-NMR of 2e Fig. 19: HMQC 1 H- 13 C spectrum of 2e Fig 20: MS (ESI) spectrum of 2e 1
2 Fig. 21: 1 H-NMR of per-(6-phenylethylamino-6-deoxy)-β-cd (2f) Fig. 22: 13 C-NMR of 2f Fig. 23: HMQC 1 H- 13 C spectrum of 2f Fig 24: MS (ESI) spectrum of 2f Fig. 25: 1 H-NMR of per-(6-methyl piperazino-6-deoxy)-β-cd (2g) Fig. 26: 13 C-NMR of 2g Fig. 27: HMQC 1 H- 13 C spectrum of 2g Fig 28: MS (ESI) spectrum of 2g Fig. 29: 1 H-NMR of per-(6-morpholino-6-deoxy)-β-cd (2h) Fig. 30: 13 C-NMR of 2h Fig. 31: HMQC 1 H- 13 C spectrum of 2h Fig 32: MS (ESI) spectrum of 2h Fig. 33: 1 H-NMR of per-(6-tetrahydroisoquinolino-6-deoxy)-β-cd (2i) Fig. 34: 13 C-NMR of 2i Fig. 35: HMQC 1 H- 13 C spectrum of 2i Fig 36: MS (ESI) spectrum of 2i Fig. 37: 1 H-NMR of per-(6(3-phenylureido)-6-deoxy)-β-cd (5a) Fig. 38: 13 C-NMR of 5a Fig. 39: HMQC 1 H- 13 C spectrum of 5a Fig 40: MS (ESI) spectrum of 5a Fig. 41: 1 H-NMR of per-(6(3-cyclohexylureido)-6-deoxy)-β-cd (5b) Fig. 42: 13 C-NMR of 5b Fig. 43: HMQC 1 H- 13 C spectrum of 5b Fig 44: MS (ESI) spectrum of 5b Fig. 45: 1 H-NMR of per-(6(3-benzylthioureido)-6-deoxy)-β-cd (6a) Fig. 46: 13 C-NMR of 6a Fig. 47: HMQC 1 H- 13 C spectrum of 6a Fig 48: MS (ESI) spectrum of 6a Fig. 49: 1 H-NMR of per-(6(3-phenylethylthioureido)-6-deoxy)-β-cd (6b) Fig. 50: 13 C-NMR of 6b Fig. 51: HMQC 1 H- 13 C spectrum of 6b Fig 52: MS (ESI) spectrum of 6b Fig. 53: 1 H-NMR of per-(6(3-butylthioureido)-6-deoxy)-β-cd (6c) Fig. 54: 13 C-NMR of 6c 2
3 Fig. 55: HMQC 1 H- 13 C spectrum of 6c Fig 56: MS (ESI) spectrum of 6c Fig 57: Chemical structure of the substituents Fig 58: PCA of the synthetized CD derivatives 3
4 Fig 1. 1 H-NMR of per-(6-benzylamino-6-deoxy)-β-cd (2a) 4
5 Fig C NMR of per-(6-benzylamino-6-deoxy)-β-cd (2a) Fig 3. HMQC spectrum (300 MHz for I H- 13 C, in DMSO-d 6 ) of per-(6-benzylamino-6-deoxy)-β-cd (2a) Fig 4. MS (ESI) spectrum of per-(6-benzylamino-6-deoxy)-β-cd (2a) 5
6 Fig 5. 1 H-NMR of per-(6-allylamino-6-deoxy)-β-cd (2b) Fig C NMR of per-(6-allylamino-6-deoxy)-β-cd (2b) 6
7 Fig 7. HMQC spectrum (300 MHz for 1 H- 13 C, in DMSO-d 6 ) of per-(6-allylamino-6-deoxy)-β-cd (2b) Fig 8. MS (ESI) spectrum of per-(6-allylamino-6-deoxy)-β-cd (2b) 7
8 Fig 9. 1 H-NMR of per-(6-butylamino-6-deoxy)-β-cd (2c) Fig C-NMR of per-(6-butylamino-6-deoxy)-β-cd (2c) 8
9 Fig 11. HMQC spectrum (300 MHz for 1 H- 13 C, in DMSO-d 6 ) of per-(6-butylamino-6-deoxy)-β-cd (2c) Fig 12. MS (ESI) spectrum of per-(6-butylamino-6-deoxy)-β-cd (2c) 9
10 Fig H-NMR of per-(6-anilino-6-deoxy)-β-cd (2d) Fig C-NMR of per-(6-anilino-6-deoxy)-β-cd (2d) 10
11 Fig 15. HMQC spectrum (300 MHz for 1 H- 13 C, in DMSO-d 6 ) of per-(6-anilino-6-deoxy)-β-cd (2d) Fig 16. MS (ESI) spectrum of per-(6-anilino-6-deoxy)-β-cd (2d) 11
12 Fig H-NMR of per-(6-(2-chlorobenzylamino)-6-deoxy)-β-cd (2e) Fig C-NMR of per-(6-(2-chlorobenzylamino)-6-deoxy)-β-cd (2e) 12
13 Fig 19. HMQC spectrum (300 MHz for 1 H- 13 C, in DMSO-d 6 ) of per-(6-(2-chlorobenzylamino)-6- deoxy)-β-cd (2e) Fig 20. ESI (MS) spectrum of per-(6-(2-chlorobenzylamino)-6-deoxy)-β-cd (2e) 13
14 Fig H-NMR of per-(6-phenylethylamino-6-deoxy)-β-cd (2f) Fig C-NMR of per-(6-phenylethylamino-6-deoxy)-β-cd (2f) 14
15 Fig 23. HMQC spectrum (300 MHz for 1 H- 13 C, in DMSO-d 6 ) of per-(6-phenylethylamino-6- deoxy)-β-cd (2f) Fig 24. ESI (MS) spectrum of per-(6-phenylethylamino-6-deoxy)-β-cd (2f) 15
16 Fig H-NMR of per-(6-methyl piperazino-6-deoxy)-β-cd (2g) Fig C-NMR of per-(6-methyl piperazino-6-deoxy)-β-cd (2g) 16
17 Fig 27. HMQC spectrum (300 MHz for 1 H- 13 C, in DMSO-d 6 ) of per-(6-methyl piperazino-6- deoxy)-β-cd (2g) Fig 28. MS (ESI) spectrum of per-(6-methyl piperazino-6-deoxy)-β-cd (2g) 17
18 Fig H-NMR of per-(6-morpholino-6-deoxy)-β-cd (2h) Fig C-NMR of per-(6-morpholino-6-deoxy)-β-cd (2h) 18
19 Fig 31. HMQC spectrum (300 MHz for 1 H- 13 C, in D 2 O) of per-(6-morpholino-6-deoxy)-β-cd (2h) Fig 32. MS (ESI) spectrum of per-(6-morpholino-6-deoxy)-β-cd (2h) 19
20 Fig H-NMR of per-(6-tetrahydroisoquinolino-6-deoxy)-β-cd (2i) Fig C NMR of per-(6-tetrahydroisoquinolino-6-deoxy)-β-cd (2i) 20
21 Fig 35. HMQC spectrum (300 MHz for I H- 13 C, in DMSO-d 6 ) of per-(6-tetrahydroisoquinolino-6- deoxy)-β-cd (2i) Fig 36. MS (ESI) spectrum of 2i 21
22 Fig H-NMR of per-(6(3-phenylureido)-6-deoxy)-β-cd (5a) Fig C NMR of per-(6(3-phenylureido)-6-deoxy)-β-cd (5a) 22
23 Fig 39. HMQC spectrum (300 MHz for I H- 13 C, in DMSO-d 6 ) of per-(6(3-phenylureido)-6-deoxy)- β-cd (5a) Fig 40. MS (ESI) spectrum of per-(6(3-phenylureido)-6-deoxy)-β-cd (5a) 23
24 Fig H-NMR of per-(6(3-cyclohexylureido)-6-deoxy)-β-cd (5b) Fig C NMR of per-(6(3-cyclohexylureido)-6-deoxy)-β-cd (5b) 24
25 Fig 43. HMQC spectrum (300 MHz for I H- 13 C, in CDCl 3 ) of per-(6(3-cyclohexylureido)-6-deoxy)- β-cd (5b) Fig 44. MS (ESI) spectrum of per-(6(3-cyclohexylureido)-6-deoxy)-β-cd (5b) 25
26 Fig H-NMR of per-(6(3-benzylthioureido)-6-deoxy)-β-cd (6a) Fig C NMR of per-(6(3-benzylthioureido)-6-deoxy)-β-cd (6a) 26
27 Fig 47. HMQC spectrum (300 MHz for I H- 13 C, in DMSO-d 6 ) of per-(6(3-benzylthioureido)-6- deoxy)-β-cd (6a) Fig 48. MS (ESI) spectrum of per-(6(3-benzylthioureido)-6-deoxy)-β-cd (6a) 27
28 Fig H-NMR of per-(6(3-phenylethylthioureido)-6-deoxy)-β-cd (6b) Fig C NMR of per-(6(3-phenylethylthioureido)-6-deoxy)-β-cd (6b) 28
29 Fig 51. HMQC spectrum (300 MHz for I H- 13 C, in DMSO-d 6 ) of per-(6(3-phenylethylthioureido)-6- deoxy)-β-cd (6b) Fig 52. MS (ESI) spectrum of per-(6(3-phenylethylthioureido)-6-deoxy)-β-cd (6b) 29
30 Fig H-NMR of per-(6(3-butylthioureido)-6-deoxy)-β-cd (6c) Fig C NMR of per-(6(3-butylthioureido)-6-deoxy)-β-cd (6c) 30
31 Fig 55. HMQC spectrum (300 MHz for I H- 13 C, in DMSO-d 6 ) of per-(6(3-butylthioureido)-6- deoxy)-β-cd (6c) Fig 56. MS (ESI) spectrum of per-(6(3-butylthioureido)-6-deoxy)-β-cd (6c) 31
32 c01 c02 c03 c04 c05 c06 c07 c08 c09 c10 c11 c12 c13 c14 c15 c16 c17 c18 c19 c20 c21 c22 c23 c24 c25 c26 c27 c28 c29 c30 c31 c32 c33 c34 c35 c36 c37 c38 c39 c40 c41 c42 c43 c44 c45 c46 c47 c48 c49 c50 c51 c52 c53 c54 c55 c56 c57 c58 c59 c60 c61 c62 c63 c64 c65 c66 c67 c68 Fig 57. Chemical structure of the substituents 32
33 PCA Substituents and CD Derivatives c15_cd c12 CD c04_cd c18_cd c60_cd PC 2 (21%) c14_cd c13_cd c39_cd c67_cd c05_cd c25_cd c38_cd c27_cd c46_cd PC 1 (27%) Fig. 58. PCA of the synthetized CD derivatives. VolSurf+ descriptors were calculated for low energy conformations of each CD, obtained as explained in the paper, and submitted to a PCA analysis. The score plot of the first two main PCs (in parenthesis the variance %) is reported. Each CD is shown with a different color and small rectangles with the same color represent the correspondent conformations. Such conformations can be grouped in the highlighted region of the score plot. The plot shows how CD derivatives can be clustered mainly on the basis of substituents properties. 33
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