Analytical Data of the Synthesized Compounds

ANALYTICAL DATA OF THE SYNTHESIZED COMPOUNDS

1. 3-(Pyridinyl)-propanals

P2PAL synthesis provided a yield of 82% and purity of 95% (LC-MS traces); MS: [M+H]+= 136.07; 1H-NMR (300 MHz, DMSO-d6): δ (ppm)2.79-2.89 (m, 2H), 3.00-3.09 (m, 2H), 7.15-7.23 (m, 1H), 7.28 (d, J=7.87 Hz, 1H), 7.68 (td, J=7.59, 1.83 Hz, 1H), 8.42-8.49 (m, 1H), 9.76 (s, 1H); 13C-NMR (300 MHz, DMSO-d6): δ (ppm) 21.6, 49.6, 121.2, 122.7, 136.3, 148.7, 159.7, 202.5. P3PAL synthesis provided a yield of 88% and purity of 97% (LC-MS traces); MS: [M+H]+= 136.07; 1H-NMR (300 MHz, DMSO-d6): δ (ppm) 2.77-2.91 (m, 4H), 7.30 (dd, J=7.68, 4.76 Hz, 1H), 7.65 (d, J=7.87 Hz, 1H), 8.40 (dd, J=4.76, 1.46 Hz, 1H), 8.46 (d, J=1.83 Hz, 1H), 9.71 (s, 1H); 13C-NMR (300 MHz, DMSO-d6): δ (ppm) 24.5, 43.7, 123.3, 135.7, 136.2, 147.1, 149.5, 202.3. P4PAL synthesis provided a yield of 87% and purity of 98% (LC-MS traces); MS: [M+H]+= 136.07;1H-NMR (300 MHz, DMSO-d6): δ (ppm) 2.80-2.90 (m, 4H), 7.16-7.31 (m, 2H), 8.37-8.51 (m, 2H), 9.71 (s, 1H);13C-NMR (300 MHz, DMSO-d6): δ (ppm) 26.5, 42.8, 123.7, 149.3, 202.1.

2. Dialkylacetals of purine-derived aldehydes: N-(2,2-dimethoxyethyl)-9H-purin-6-amine (Pu-AEAL dimethylacetal), N-(3,3-diethoxypropyl)-9H-purin-6-amine (Pu-APAL diethylacetal) and N-(4,4-diethoxybutyl)-9H-purin-6-amine (Pu-ABAL diethylacetal)

In the case of Pu-AAAL dimethylacetal, the procedure provided a yield of 44% and purity of 99% (LC-MS traces); MS: [M+H]+= 224.01;1H-NMR (300 MHz, DMSO-d6): δ(ppm) 3.29 (s, 6H), 3.58-3.62 (m, 2H), 4.64 (t, J=4.67 Hz, 1H), 7.49 (br. s., 1H), 8.11 (s, 1H), 8.20 (br. s., 1H), 12.93 (br. s., 1H). For Pu-APAL diethylacetal, there was a yield of 64% andpurity of 96% (LC/MS traces);MS: [M+H]+= 266.02;1H-NMR (300 MHz, DMSO-d6): δ(ppm) 1.11 (t, J=7.04 Hz, 6H), 1.86 (q, J=6.65 Hz, 2H), 3.38-3.66 (m, 6H), 4.59 (t, J=5.49 Hz, 1H), 7.53 (br. s., 1H), 8.08 (s, 1H), 8.18 (s, 1H), 12.86 (br. s., 1H).ForPu-ABAL diethylacetal, there was a yield of53% and purity of 97% (LC/MS traces);MS: [M+H]+= 280.08; 1H-NMR (300 MHz, DMSO-d6): δ(ppm) 1.08 (t, J=7.04 Hz, 6H), 1.55-1.60 (m., 4H), 3.36-3.62 (m, 6H), 4.48 (t, J=5.03 Hz, 1H), 7.64 (br. s., 1H), 8.07 (br. s., 1H), 8.16 (br. s., 1H), 12.87 (br. s., 1H).

3.Dialkylacetals of 7-deazapurine-derived aldehydes: N-(2,2-dimethoxyethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (PyrPm-AEAL dimethylacetal), N-(3,3-diethoxypropyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (PyrPm-APAL diethylacetal) and N-(4,4-diethoxybutyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (PyrPm-ABAL diethylacetal)

In the case of PyrPm-AAAL dimethylacetal, the procedure provided a yield of 79% andpurity of 98% (LC/MS traces);MS: [M+H]+= 223.11, 1H-NMR (300 MHz, DMSO-d6): δ(ppm)3.31 (s, 6H), 3.57 (t, J=5.67 Hz, 2H), 4.60 (t, J=5.40 Hz, 1H), 6.59 (m, J=1.83 Hz, 1H), 7.03-7.10 (m, 1H), 7.45 (t, J=5.31 Hz, 1H), 8.11 (s, 1H), 11.48 (br. s., 1H);13C-NMR (300 MHz, DMSO-d6): δ(ppm) 41.7, 53.2, 98.5, 102.0, 102.4, 120.7, 150.0, 151.2, 155.9. For PyrPm-APAL diethylacetal, there was a yield of 89% and purity of 99% (LC/MS traces);MS: [M+H]+= 265.21, 1H-NMR (300 MHz, DMSO-d6): δ(ppm) 1.11 (t, J=7.04 Hz, 6H), 1.86 (q, J=6.53 Hz, 2H), 3.37-3.66 (m, 6H), 4.60 (t, J=5.58 Hz, 1H), 6.47-6.55 (m, 1H), 7.00-7.09 (m, 1H), 7.30 (br. s., 1H), 8.09 (s, 1H), 11.45 (br. s., 1H);13C-NMR (300 MHz, DMSO-d6): δ(ppm) 15.2, 33.4, 36.1, 60.5, 98.3, 100.6, 102.4, 120.5, 150.0, 151.3, 156.0. For PyrPm-ABAL diethylacetal, there was a yield of 47% and purity of 98% (LC/MS traces);MS: [M+H]+= 279.19; 1H-NMR (300 MHz, DMSO-d6): δ(ppm) 1.09 (t, J=7.04 Hz, 6H), 1.55-1.60 (m, 4H), 3.36-3.60 (m, 6H), 4.46-4.54 (m, 1H), 6.50-6.57 (m, 1H), 7.01-7.07 (m, 1H), 7.33 (t, J=5.21 Hz, 1H), 8.08 (s, 1H), 11.42 (br. s., 1H);13C-NMR (300 MHz, DMSO-d6): δ(ppm) 15.2, 24.6, 30.9, 60.5, 98.4, 102.0, 102.3, 120.4, 150.0, 151.3. 156.0.

4. Dialkylacetals of pyrimidine-derived aldehydes: N-(2,2-dimethoxyethyl)pyrimidin-2-amine (Pm-AEAL dimethylacetal), N-(3,3-diethoxypropyl)pyrimidin-2-amine (Pm-APAL diethylacetal) and N-(4,4-diethoxybutyl)pyrimidin-2-amine (Pm-ABAL diethylacetal)

In the case of Pm-AAAL dimethylacetal, the procedure provided a yield of 45% and purity of 99% (LC/MS traces);MS: [M+H]+= 184.20, 1H-NMR (300 MHz, chloroform-d):δ(ppm)3.30-3.46 (m, 6H), 3.57 (t, J=5.63 Hz, 2H), 4.50 (t, J=5.49 Hz, 1H),5.63 (br. s., 1H), 6.52 (m, 1H), 8.26 (d, J=4.94 Hz, 2H);13C-NMR (300 MHz, chloroform-d):δ(ppm) 42.3, 53.5, 102.2, 110.1, 157.4, 161.7. For Pm-APAL diethylacetal, there was a yield of 57% andpurity of 98% (LC/MS traces);MS: [M+H]+= 226.19, 1H-NMR (300 MHz, chloroform-d):δ(ppm) 1.20 (t, J=7.14 Hz, 6H), 1.93 (q, J=6.22 Hz, 2 H), 3.40-3.57 (m, 4 H), 3.58-3.75 (m, 2 H), 4.62 (t, J=5.49 Hz, 1 H), 5.73 (br. s., 1 H), 6.47 (t, J=4.80 Hz, 1 H), 8.24 (d, J=4.67 Hz, 2 H);13C-NMR (300 MHz, chloroform-d):δ(ppm) 14.7, 32.6, 37.0, 60.9, 101.3, 109.7, 157.3, 161.7. For Pm-ABAL diethylacetal, there was a yield of 49% and purity of 95% (LC/MS traces);MS: [M+H]+= 240.12;1H-NMR (300 MHz, chloroform-d):δ(ppm) 1.21 (t, J=7.00 Hz, 6H), 1.72 (m, 4H), 3.38-3.57 (m, 4H), 3.59-3.76 (m, 2H), 4.53 (m., 1H), 5.59 (br. s., 1H), 6.46-6.55 (m, 1H), 8.26 (d, J=4.67 Hz, 2H);13C-NMR (300 MHz, chloroform-d):δ(ppm) 14.7, 24.2, 30.5, 40.6, 60.6, 102.1, 109.6, 157.3, 161.6.

5. Dialkylacetals of (pyridinylmethylamino)-aldehydes

2-PMet-APAL diethylacetal i.e. 3,3-diethoxy-N-(2-pyridin-2-ylmethyl)propan-1-amine

MS: [M+H]+= 239.04;1H-NMR (300 MHz, DMSO-d6):δ(ppm) 1.08 (t, J=7.04 Hz, 6 H), 1.67 (q, J=6.77 Hz, 2 H), 2.46 - 2.59 (m, 2 H), 3.33 - 3.61 (m, 6 H), 4.52 - 4.61 (m, 1 H), 7.22 (dd, J=6.77, 5.12 Hz, 1 H), 7.41 (d, J=7.87 Hz, 1 H), 7.68 - 7.77 (m, 1 H), 8.47 (d, J=4.02 Hz, 1 H);13C-NMR (300 MHz, DMSO-d6):δ (ppm) 15.8, 34.4, 45.2, 55.3, 61.0, 101.6, 122.2, 122.3, 136.8, 149.2, 161.1.

2-PMet-ABAL diethylacetal i.e. 4,4-diethoxy-N-(2-pyridin-2-ylmethyl)butan-1-amine

MS: [M+H]+= 253.05; 1H-NMR (300 MHz, DMSO-d6): δ (ppm) 1.09 (t, J=7.04 Hz, 6 H), 1.39 - 1.60 (m, 4 H), 2.48 - 2.57 (m, 2 H), 3.33 - 3.60 (m, 6 H), 4.43 (t, J=5.31 Hz, 1 H), 7.19 - 7.27 (m, 1 H), 7.42 (d, J=7.87 Hz, 1 H), 7.70 - 7.79 (m, 1 H), 8.44 - 8.52 (m, 1 H);13C-NMR (300 MHz, DMSO-d6):δ(ppm) 15.8, 25.1, 31.6, 49.1, 54.9, 60.9, 102.7, 122.3, 122.4, 136.9, 149.2, 160.6.

3-PMet-APAL diethylacetal i.e. 3,3-diethoxy-N-(2-pyridin-3-ylmethyl)propan-1-amine

MS [M+H]+= 239.04;1H-NMR (300 MHz, DMSO-d6):δ(ppm) 1.07 (t, J=7.04 Hz, 6 H), 1.61 - 1.71 (m, 2 H), 2.45 - 2.54 (m, 2 H), 3.33 - 3.59 (m, 6 H), 4.56 (t, J=5.67 Hz, 1 H), 7.29 - 7.36 (m, 1 H), 7.71 (d, J=7.87 Hz, 1 H), 8.42 (dd, J=1.65 Hz, 1 H), 8.50 (d, J=1.46 Hz, 1 H); 13C-NMR (300 MHz, DMSO-d6):δ(ppm) 15.8, 34.3, 44.9, 50.9, 61.1, 101.5, 123.8, 136.1, 136.8, 148.3, 149.9.

3-PMet-ABAL diethylacetal i.e. 4,4-diethoxy-N-(2-pyridin-3-ylmethyl)butan-1-amine

MS [M+H]+= 253.03;1H-NMR (300 MHz, DMSO-d6):δ(ppm) 1.08 (t, J=7.04 Hz, 6 H), 1.38 - 1.57 (m, 4 H), 2.45 (t, J=6.77 Hz, 2 H), 3.33 - 3.59 (m, 6 H), 4.41 (t, J=5.40 Hz, 1 H), 7.32 (dd, J=7.50, 4.94 Hz, 3 H), 7.71 (d, J=7.87 Hz, 3 H), 8.42 (dd, J=4.76 Hz, 3 H), 8.50 (d, J=1.46 Hz, 3 H);13C-NMR (300 MHz, DMSO-d6):δ(ppm) 15.8, 25.3, 31.6, 48.9, 50.8, 60.9, 102.7, 123.8, 136.1, 136.9, 148.3, 149.9.

4-PMet-APAL diethylacetal i.e. 3,3-diethoxy-N-(2-pyridin-4-ylmethyl)propan-1-amine

MS [M+H]+= 239.04;1H-NMR (300 MHz, DMSO-d6):δ(ppm) 1.07 (t, J=7.04 Hz, 6 H), 1.67 (q, J=6.59 Hz, 2 H), 2.49 (t, J=6.95 Hz, 2 H), 3.33 - 3.60 (m, 6 H), 4.57 (t, J=5.58 Hz, 1 H), 7.33 (d, J=5.12 Hz, 2 H), 8.48 (d, J=5.12 Hz, 2 H);13C-NMR (300 MHz, DMSO-d6):δ(ppm) 15.8, 34.2, 44.9, 52.2, 61.3, 101.4, 123.5, 149.9, 150.3.

4-PMet-APAL diethylacetal i.e. 4,4-diethoxy-N-(2-pyridin-4-ylmethyl)butan-1-amine

MS [M+H]+= 253.07; 1H-NMR (300 MHz, DMSO-d6):δ(ppm) 1.10 (t, J=7.04 Hz, 6 H), 1.38 - 1.58 (m, 4 H), 2.45 (t, J=6.86 Hz, 2 H), 3.33 - 3.59 (m, 6 H), 4.42 (t, J=5.40 Hz, 1 H), 7.27 - 7.36 (m, 2 H), 8.43 - 8.51 (m, 2 H);13C-NMR (300 MHz, DMSO-d6):δ(ppm) 15.8, 25.3, 31.6, 49.0, 52.2, 60.9, 102.7, 123.4, 149.8, 150.7.