Biomimetics, Vol. 7, Pages 247: Anticancer Activity of Thiophene Carboxamide Derivatives as CA-4 Biomimetics: Synthesis, Biological Potency, 3D Spheroid Model, and Molecular Dynamics Simulation

3.2. Chemical Characterization

Solid product M.P. 203.5–205 °C, HRMS (m/z): [M+H]+ Calc. 298.0702 found 298.0684. 1H NMR (DMSO-d6) δ: 10.25 (1H, s, NH), 8.03 (1H, d, J = 4 Hz, Ar-H), 7.80 (2H, t, J = 5 Hz, Ar-H), 7.75 (2H, d, J = 8 Hz, Ar-H), 7.60 (1H, d, J = 3.5 Hz, Ar-H), 7.37 (2H, t, J = 7.5 Hz, Ar-H), 7.31 (2H, t, J = 8.5 Hz, Ar-H), 7.12 (1H, t, J = 7.5 Hz, Ar-H). 13C NMR (DMSO-d6) δ ppm: 163.66, 161.70, 160.08, 147.66, 139.44, 139.12, 130.69, 130.13, 130.10, 129.15, 128.41, 128.34, 125.02, 124.25, 120.82, 116.76, 116.59.

Solid product M.P. 190.8–192.0 °C, HRMS (m/z): [M+H]+ calc 388.1019 found 388.1073. 1H NMR (DMSO-d6) δ: 10.16 (1H, s, NH), 8.00 (1H, d, J = 3.5 Hz, Ar-H), 7.80 (2H, t, J = 5.5 Hz, Ar-H), 7.60 (1H, d, J = 4 Hz, Ar-H), 7.31 (2H, t, J = 9 Hz, Ar-H), 7.17 (2H, s, Ar-H), 3.79 (6H, s, 3,5-OCH3), 3.65 (3H, s, 4-OCH3). 13C NMR (DMSO-d6) δ ppm: 163.66, 161.70, 159.92, 153.11, 147.65, 139.49, 135.23, 134.25, 130.48, 128.39, 128.33, 125.05, 116.77, 116.59, 98.47, 60.57, 56.21.

Solid product M.P. 218.5–220.4 °C, HRMS (m/z): [M+H]+ Calc. 354.1328, found 354.1347. 1H NMR (DMSO-d6) δ: 10.19 (1H, s, NH), 8.02 (1H, d, J = 4 Hz, Ar-H), 7.80 (2H, t, J = 7 Hz, Ar-H), 7.65 (2H, d, J = 8.5 Hz, Ar-H), 7.59 (1H, d, J = 3.5 Hz, Ar-H), 7.38 (2H, d, J = 8.5 Hz, Ar-H), 7.31 (2H, t, J = 8.5 Hz, Ar-H), 1.28 (9H, s, 4-t-butyl). 13C NMR (DMSO-d6) δ ppm: 163.64, 161.68, 159.93, 147.50, 146.58, 139.61, 136.54, 130.51, 130.16, 128.39, 125.77, 125.00, 120.56, 116.75, 34.53, 31.65

Solid product M.P. 156.5–157.0 °C, HRMS (m/z): [M+H]+ Calc. 358.0913 found 358.0392. 1H NMR (DMSO-d6) δ: 10.16 (1H, s, NH), 8.02 (1H, d, J = 4 Hz, Ar-H), 7.80 (2H, t, J = 6 Hz, Ar-H), 7.60 (1H, d, J = 4 Hz, Ar-H), 7.31 (2H, t, J = 8.5 Hz, Ar-H), 7.03 (2H, s, Ar-H), 6.28 (1H, s, Ar-H), 3.75 (6H, s, 3,5-OCH3). 13C NMR (DMSO-d6) δ ppm: 163.68, 161.72, 160.88, 160.10, 147.80, 140.81, 139.39, 130.69, 130.09, 128.35, 125.04, 116.60, 98.93, 96.29, 92.82, 55.60.

Solid product M.P. 185.5–187.5 °C, HRMS (m/z): [M+H]+ Calc. 392.0588 found 358.0581. 1H NMR (DMSO-d6) δ: 9.64 (1H, s, NH), 8.02 (1H, d, J = 4 Hz, Ar-H), 7.80 (2H, t, J = 8.5 Hz, Ar-H), 7.58 (2H, d, J = 7 Hz, Ar-H), 7.31 (2H, t, J = 9 Hz, Ar-H), 7.22 (1H, s, Ar-H), 3.83, 3.81 (6H, s, 2,5-OCH3). 13C NMR (DMSO-d6) δ ppm: 160.06, 148.51, 147.77, 146.44, 138.77, 130.94, 128.45, 128.38, 126.24, 125.13, 117.61, 116.77, 116.59, 113.97, 110.54, 57.01, 56.96.

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