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Molecules 2018, 23, 1436 8 of 13 J = 8.0 Hz, 1H), 7.78 (d, J = 9.2 Hz, 1H), 7.45–7.41 (m, 2H), 7.35 (dd, J = 7.5, 8.2 Hz, 1H), 7.25 (d, J = 8.2 Hz, 1H), 6.54 (d, J = 7.5 Hz, 1H), 6.27 (brs, 1H), 5.07 (brs, 1H), 3.64 (t, J = 6.0 Hz, 2H), 3.50 (brs, 4H), 3.32 (t, J = 6.0 Hz, 2H), 2.64 (d, J = 6.0 Hz, 2H), 2.38 (t, J = 6.0 Hz, 2H), 2.29 (brs, 4H). 13C- NMR (CDCl3): δ 171.8, 142.9, 134.4, 128.6, 126.5, 125.8, 124.8, 123.7, 120.0, 117.7, 104.4, 66.7, 56.8, 53.2, 40.3, 35.5, 35.3. ESI-MS m/z: [M + H]+ calcd for C19H25N3O2+ 328.2, found 328.3. 3.2.5. Synthesis of N-Ethyl-N-(5-(3-(2-morpholinoethylamino)-3-oxopropylamino)-9H-benzo[a] phenoxazin-9-ylidene)ethanaminium Chloride (PS2, C29H36ClN5O3) To a cold solution of compound 4 (50 mg, 0.2 mmol, 1 equiv) in EtOH (5 mL) was added compound 5 (60 mg, 0.2 mmol, 1 equiv) and 5 drops of concentrated HCl. The mixture was refluxed for 4 h. The solution was evaporated and purified by silica gel flash chromatography using CH2Cl2/MeOH (10:1) as eluent to give compound PS2 as a blue solid (54 mg, 0.11 mmol, 55% yield). 1H-NMR (CD3OD): δ 8.72 (s, 1H), 8.39 (s, 1H), 7.84 (s, 1H), 7.75 (s, 2H), 7.25 (s, 1H), 6.85 (s, 1H), 4.04–3.96 (m, 6H), 3.70–3.66 (m, 8H), 3.34 (s, 2H), 3.18 (s, 2H), 2.91 (s, 2H), 1.35 (s, 6H). 13C-NMR (CD3OD): δ 174.1, 158.9, 155.8, 152.9, 149.7, 134.5, 134.2, 132.9, 132.3, 131.9, 130.8, 125.4, 124.5, 124.2, 117.0, 96.9, 94.6, 64.8, 58.1, 53.4, 41.8, 35.1, 34.7, 13.0. ESI-MS m/z [M]+ 502.2. HR-ESIMS: [M]+ calcd for C29H36N5O3+ 502.2813, found 502.2812; [M + H]2+ calcd for C29H36N5O32+ 251.6442, found 251.6445. 3.2.6. Synthesis of tert-Butyl 2-(3-(naphthalen-1-ylamino)propanamido)ethylcarbamate (6, C20H27N3O3) Compound 2 (100 mg, 0.5 mmol, 1 equiv) was dissolved in CH2Cl2 (10 mL), and then tert-butyl (2-aminoethyl)carbamate (149 mg, 1.0 mmol, 2 equiv), HATU (200 mg, 0.5 mmol, 1 equiv) and iPrNEt2 (0.2 mL, 1 mmol, 2 equiv) was added. The mixture was stirred overnight, and then concentrated. The residue was purified by silica gel chromatography with CH2Cl2/MeOH (10:1) as eluent to give compound 6 as a white solid (160 mg, 0.48 mmol, 96% yield). 1H-NMR (CDCl3): δ 7.91–7.89 (m, 1H), 7.79–7.77 (m, 1H), 7.45–7.41 (m, 2H), 7.46–7.43 (m, 1H), 7.34 (dd, J = 7.6, 8.0 Hz, 1H), 7.27 (d, J = 7.0 Hz, 1H), 6.6 (d, J = 7.6 Hz, 1H), 6.48 (brs, 1H), 4.85 (brs, 1H), 3.61 (t, J = 6.0 Hz, 2H), 3.37–3.34 (m, 2H), 3.26–3.24 (m, 2H), 2.63 (t, J = 6.0 Hz, 2H), 1.41 (s, 9H). 13C-NMR (CDCl3): δ 172.6, 157.2, 142.9, 134.5, 128.7, 126.6, 126.0, 125.1, 124.0, 120.3, 118.2, 105.0, 80.0, 41.1, 40.8, 40.3, 35.2, 28.4. ESI-MS m/z: [M + H]+ calcd for C20H28N3O3+ 484.2, found 358.0. 3.2.7. Synthesis of N-(2-(3-(Naphthalen-1-ylamino)propanamido)ethyl)-5-(2-oxohexahydro-1H -thieno[3,4-d]imidazol-4-yl)pentanamide (7, C25H33N5O3S) To a cold (ice bath) solution of 6 (120 mg, 0.34 mmol, 1 equiv) in CH2Cl2 (5 mL) was added trifluoroacetic acid (100 μL, 1 mmol, 2.9 equiv) under 0 ◦C. The mixture was stirred overnight, and then concentrated to give a residue, which was used in the next step without further purification. The obtained residue was dissolved in CH3CN (5 mL), and then Biotin-NHS (172 mg, 0.50 mmol, 1.5 equiv), and Et3N (0.2 mL, 1 mmol, 2.9 equiv) were added. The mixture was stirred overnight, and then concentrated. The residue was purified by silica gel chromatography with CH2Cl2/MeOH (10:1) as eluent to give compound 7 as a white solid (85 mg, 0.18 mmol, 52% yield). 1H-NMR (DMSO-d6): δ 8.08 (d, J = 8.3 Hz, 1H), 7.99 (brs, 1H), 7.81 (brs, 1H), 7.75 (d, J = 8.3 Hz, 1H), 7.43 (ddd, J = 1.0, 6.7, 8.4 Hz, 1H), 7.39 (ddd, J =1.4, 6.8, 9.0 Hz, 1H), 7.29 (dd, J = 7.8, 7.9 Hz, 1H), 7.11 (d, J = 8.2 Hz, 1H), 6.54 (d, J = 8.6 Hz, 1H), 6.42 (s, 1H), 6.35 (s, 1H), 6.19 (dd, J = 5.4, 5.5 Hz, 1H), 4.28–4.26 (m, 1H), 4.11–4.09 (m, 1H), 3.44–3.41 (m, 1H), 3.31 (m, 5H), 2.78 (dd, J = 5.1, 12.5 Hz, 1H), 2.56(d, J = 12.5 Hz, 1H), 2.04 (t, J = 1.1 Hz, 1H), 1.61–1.57 (m, 1H), 1.53–1.43 (m, 3H), 1.32–1.23 (m, 2H), 1.17 (t, J = 7.3 Hz, 1H).13C-NMR (DMSO-d6): δ 172.4, 171.1, 162.7, 143.8, 134.0, 127.9, 126.8, 125.6, 124.0, 123.0, 121.4, 115.6, 102.9, 61.0, 59.2, 55.4, 45.7, 40.1, 38.5, 38.3, 35.3, 34.8, 28.2, 28.0, 25.2. ESI-MS m/z: [M + H]+ calcd for C25H34N5O3S+ 484.2, found 484.3.PDF Image | Photosensitizers for Anticancer Photodynamic Therapy
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