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small-molecule pharmacokinetic and toxicity properties using graph-based signatures","volume":"58","author":"Pires","year":"2015","journal-title":"J Med Chem"},{"key":"10.1016\/j.bmcl.2025.130467_bb0250","unstructured":"Spectral data of 11e (KMCA-0011): mp 130\u2013132 \u00b0C; 1H NMR (400 MHz, CDCl3) \u03b4 7.85 (s, 1H), 7.82 (d, J = 2.0 Hz, 1H), 7.59 (d, J = 8.8 Hz, 1H), 7.45 (dd, J = 8.8, 2.0 Hz, 1H), 7.29 (t, J = 7.4 Hz, 2H), 7.22\u20137.13 (m, 3H), 3.60 (s, 2H), 2.97 (d, J = 11.2 Hz, 2H), 2.64 (t, J = 5.9 Hz, 2H), 2.57 (d, J = 7.1 Hz, 2H), 2.05 (t, J = 11.2 Hz, 2H), 1.69 (d, J = 12.4 Hz, 2H), 1.64\u20131.54 (m, 1H), 1.37 (qd, J = 12.4 and 3.2 Hz, 2H); 13C NMR (125 MHz, DMSO\u2011d6) \u03b4 157.5, 155.2, 149.5, 141.6, 140.8, 130.3, 129.5, 128.6, 128.0, 126.2, 121.2, 113.9, 57.1, 53.7, 42.8, 37.7, 37.3, 32.1; HRMS (ESI+): m\/z calcd. for C22H24ClN3O2 [M+H]+ 398.1630 and 400.1600, found 398.16237 and 400.15930."},{"key":"10.1016\/j.bmcl.2025.130467_bb0255","unstructured":"Spectral data of 21b (KMCA-0002): mp 155\u2013158 \u00b0C; 1H NMR (400 MHz, DMSO\u2011d6) \u03b4 10.45 (s, 1H), 9.77 (s, 1H), 8.90 (t, J = 5.6 Hz, 1H), 8.11 (d, J = 7.6 Hz, 1H), 7.27 (t, J = 7.3 Hz, 2H), 7.20\u20137.12 (m, 3H), 6.99 (t, J = 7.6 Hz, 1H), 6.92 (d, J = 7.6 Hz, 1H), 6.83 (t, J = 7.6 Hz, 1H), 3.29 (q, J = 5.6 Hz, 2H), 2.84 (d, J = 11.6 Hz, 2H), 2.48 (s, 2H: DMSO peak-overlapped), 2.40 (t, J = 6.0 Hz, 2H), 1.85 (t, J = 11.6 Hz, 2H), 1.51 (d, J = 12.9 Hz, 2H), 1.48\u20131.37 (m, 1H), 1.23\u20131.10 (m, 2H); 13C NMR (100 MHz, CDCl3) \u03b4 159.5, 157.7, 147.9, 140.4, 129.1, 128.2, 127.0, 125.9, 124.5, 121.7, 120.5, 117.9, 56.5, 53.7, 42.9, 37.7, 36.5, 31.5; HRMS (ESI+): m\/z calcd. for C22H27N3O3 [M+H]+ 382.2125, found 382.2117."},{"key":"10.1016\/j.bmcl.2025.130467_bb0260","unstructured":"Spectral data of 21e (KMCA-0028): mp 193\u2013195 \u00b0C; 1H NMR (400 MHz, DMSO\u2011d6) \u03b4 9.92 (s, 1H), 9.76 (s, 1H), 8.88 (t, J = 5.8 Hz, 1H), 7.81 (d, J = 3.0 Hz, 1H), 7.27 (t, J = 7.4 Hz, 2H), 7.20\u20137.12 (m, 3H), 6.83 (d, J = 8.8 Hz, 1H), 6.59 (dd, J = 8.8 and 3.0 Hz, 1H), 3.68 (s, 3H), 3.28 (q, J = 5.8 Hz, 2H), 2.84 (d, J = 11.2 Hz, 2H), 2.48 (s, 2H: DMSO peak-overlapped), 2.40 (t, J = 6.7 Hz, 2H), 1.85 (t, J = 11.2 Hz, 2H), 1.52 (d, J = 12.7 Hz, 2H), 1.48\u20131.39 (m, 1H), 1.22\u20131.11 (m, 2H); 13C NMR (100 MHz, DMSO\u2011d6) \u03b4 159.4, 157.0, 151.9, 140.4, 140.3, 128.9, 128.0, 125.6, 125.3, 115.0, 109.3, 105.6, 56.4, 55.2, 53.1, 42.3, 37.3, 36.7, 31.6; HRMS (ESI+): m\/z calcd. for C23H29N3O4 [M+H]+ 412.2231, found 412.22256."}],"container-title":["Bioorganic & Medicinal Chemistry 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