On the other hand, the Pvalue for 3m corresponds to those of standard drugs with high CNS permeability (Table 6)

On the other hand, the Pvalue for 3m corresponds to those of standard drugs with high CNS permeability (Table 6). Table 6 Prediction of the BBB penetration of drugs expressed as the apparent permeability coefficient (P SEM (10?6 cm s?1) /th th align=”center” valign=”middle” style=”border-top:solid thin;border-bottom:solid thin” rowspan=”1″ colspan=”1″ CNS (+/?) a /th th align=”center” valign=”middle” style=”border-top:solid thin;border-bottom:solid thin” rowspan=”1″ colspan=”1″ N b /th /thead 3e 13.51 1.54CNS ?3 3n 14.61 1.88CNS ?3 3c 12.28 2.33CNS ?3 3m 18.48 2.37CNS +4THA22.29 2.01CNS +4Donepezil24.19 2.83CNS +4Rivastigmine28.63 4.64CNS +5Propranolol23.06 2.06CNS +5Antipyrine17.19 1.82CNS +3Furosemide13.89 0.92CNS ?3Obidoxime14.35 0.52CNS ?4 Open in a separate window a CNS+ and CNS? represent the final predictions of the compound capability to cross or not to cross the BBB, respectively. 1.68C1.59 (m, 2H), 1.50 (m, = 15.0, 5.3, 4.4 Hz, 3H), 1.13C1.00 (m, 3H). 13C-NMR (126 MHz, dmso) 141.09, 138.37, 130.15, 128.09, 127.00, 120.94, 57.68, 54.59, 29.72, 24.68, 23.99. HRMS (ESI+): [M + H]+: calculated for C19H22N+ (= 7.6, 1.0 Hz, 2H), 7.94 (dd, = 7.6, 1.0 Hz, 2H), 7.53 (td, = 7.6, 1.0 Hz, 2H), 7.41 (td, = 7.6, 1.0 Hz, 2H), 5.63 (s, 1H), 2.25C2.15 (m, 1H), 0.85C0.76 (m, 2H), 0.55C0.46 (m, 2H). 13C-NMR (126 MHz, dmso) 141.38, 138.07, 130.14, 127.95, 127.08, 120.82, 60.17, 26.24, 3.50. HRMS (ESI+): [M + H]+: calculated for C16H16N+ (= 7.6, 1.0 Hz, 2H), 7.92 (dd, = 7.6, 1.0 Hz, 2H), 7.52 (td, = 7.6, 1.0 Hz, 2H), 7.40 (td, = 7.6, 1.0 Hz, 2H), 5.57 (s, 1H), 3.12 (p, = 9.1, 8.6 Hz, 1H), 2.22C2.10 (m, 2H), 1.62C1.41 (m, 4H). 13C-NMR (126 MHz, dmso) 141.23, 137.87, 130.16, 127.97, 126.96, 120.84, 58.50, 47.72, 27.67, 15.64. HRMS (ESI+): [M + Alpha-Naphthoflavone H]+: calculated for C17H18N+ (= 7.6, 1.0 Hz, 2H), 7.94 (dd, = 7.6, 1.0 Hz, 2H), 7.55 (td, = 7.6, 1.0 Hz, 2H), 7.42 (td, = 7.6, 1.0 Hz, 2H), 5.72 (s, 1H), 3.23 (d, = 11.7 Hz, 2H), 2.79 (q, = 11.7 Hz, 2H), 2.07 (q, = 12.6, 11.7 Hz, 2H), 1.67 (d, = 12.6 Alpha-Naphthoflavone Hz, 3H), 1.34C1.20 (m, 1H). 13C-NMR (126 MHz, dmso) 141.83, 135.94, 130.66, 128.29, 128.17, 120.91, 67.23, 49.46, 22.29, 21.67. HRMS (ESI+): [M + H]+: calculated for C18H20N+ (= 7.6, 1.0 Hz, 2H), 7.93 (dd, = 7.6, 1.0 Hz, 2H), 7.53 (td, = 7.6, 1.0 Hz, 2H), 7.42 (td, = 7.6, 1.0 Hz, 2H), 5.59 (s, 1H), 3.47 (t, = 5.2 Hz, 2H), 3.19 (s, 3H), 2.47C2.40 (m, 2H). 13C-NMR (126 MHz, dmso) 141.42, 137.56, 130.27, 128.26, 126.69, 120.93, 67.03, 59.32, 58.16, 40.87. HRMS (ESI+): [M + H]+: calculated for C16H18NO+ (= 9.3 Hz, 2H), 8.12 Alpha-Naphthoflavone (dd, = 7.6, 1.0 Hz, 2H), 7.94 (dd, = 7.6, 1.0 Hz, 2H), 7.53 (td, = 7.6, 1.0 Hz, 2H), 7.42 (td, = 7.6, 1.0 Hz, 2H), 5.61 (d, = 3.5 Hz, 1H), 2.51C2.48 (m, 2H), 1.14 (t, = 7.2 Hz, 3H). 13C-NMR (126 MHz, dmso) 141.29, 137.89, 130.19, 128.18, 126.72, 120.91, 59.17, 37.35, 11.53. HRMS (ESI+): [M + H]+: calculated for C15H16N+ (= 7.6, 1.0 Hz, 2H), 7.98 (dd, = 7.6, 1.0 Hz, 2H), 7.57 (td, = 7.6, 1.0 Hz, 2H), 7.44 (td, = 7.6, 1.0 Hz, 2H), 5.85 (s, 1H), 3.12C3.02 (m, 1H), 3.02C2.94 (m, 1H), 1.30 (t, = 7.2 Hz, 6H). 13C-NMR (126 MHz, dmso) 141.62, 136.45, 130.54, 128.37, 127.49, 121.07, 63.15, 46.29, 10.32. HRMS (ESI+): [M + H]+: calculated for C17H20N+ (= 7.6, 1.0 Hz, 2H), 7.59 (dd, = 7.6, 1.0 Hz, 2H), 7.42 (td, = 7.6, 1.0 Hz, 2H), 7.34 (td, = 7.6, 1.0 Hz, 2H), 5.03 (s, 1H), 3.31C2.71 (m, 8H), 2.68 (s, 3H). 13C-NMR (126 MHz, dmso) 143.00, 140.64, 128.64, 127.51, 125.88, 120.36, 68.65, 53.41, 45.50, 42.34. HRMS (ESI+): [M + H]+: calculated for C18H21N2+ (= 7.6, 1.0 Hz, 2H), 7.59 (dd, = 7.6, 1.0 Hz, Alpha-Naphthoflavone 2H), 7.42 (td, = 7.6, 1.0 Hz, 2H), 7.33 (td, = 7.6, 1.0 Hz, 2H), 5.03 (s, 1H), 3.02 (q, = 7.3 Hz, 2H), 2.99C2.61 (m, 8H), 1.19 (t, = 7.3 Hz, 3H). 13C-NMR (126 MHz, dmso) 143.05, 140.63, 128.62, 127.49, 125.90, 120.34, 68.67, 51.28, 50.79, 45.45, 9.01. HRMS (ESI+): [M + H]+: calculated for C19H24N2+ (m/z): 279.18612; found: 279.18555. LC-MS purity 99%. 2.2.12. 4-(9= 7.6, 1.0 Hz, 2H), 7.96 (dd, = 7.6, 1.0 Hz, 2H), 7.58 (td, = 7.6, 1.0 Hz, 2H), 7.45 (td, = 7.6, 1.0 Hz, 2H), Hepacam2 5.81 (s, 1H), 4.18C3.93 (m, 2H), 3.94C3.75 (m, 2H), Alpha-Naphthoflavone 3.31C3.09 (m, 2H), 3.09C2.87 (m, 2H). 13C-NMR (126 MHz, DMSO) 142.19, 131.09, 128.60, 128.46, 121.30, 67.38, 63.41, 48.58. HRMS (ESI+): [M + H]+: calculated for C17H18NO+ (= 7.6, 1.0 Hz, 2H), 7.93 (dd, = 7.6, 1.0 Hz, 2H), 7.52 (td, = 7.6, 1.0 Hz, 2H), 7.42 (td, = 7.6, 1.0.