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a) E. E. Smissman, A. Terada, S. El-antably, J. Med. Chem., 1976, 19, 165.
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Smissman, E.E.1
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b) J. J. McGuire, C. A. Russell, W. E. Bolanowska, et al., Cancer Res., 1990, 50, 1726.
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McGuire, J.J.1
Russell, C.A.2
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Chin. J. Inorg. Chem
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Wang, L.Z.1
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6
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0010567592
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(1971)
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7
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0032554967
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c) Y. Satoh, S. De Lombaert, N. Marcopulos, et al., Tetrahedron Lett., 1998, 39, 3367.
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(1998)
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Satoh, Y.1
De Lombaert, S.2
Marcopulos, N.3
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11
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33846684596
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4a: yield 64, Mp 182-184°C; HPLC-MS, m/z 377.8, calculated for C21H23N5O2 377.4; 1H NMR (DMSO-d6, 400MHz, δ ppm, 8.0(d, 1H, J=8.0Hz, CONH, 7.29-7.9(m, 8H, Ar-H, 4.9(m, 1H, NCH, 4.38-4.21(m, 3H, OCH 2CH, 1.8-1.55(m, 3H, CH2CH, 0.88(m, 6H, 2CH3, 13C NMR (DMSO-d6, 100MHz, δ ppm, 159.2(1C, 155.8(1C, 143.7(2C, 140.7(2C, 127.3 (2C, 127.0 (2C, 125.3(2C, 120.0(2C, 65.6(1C, 46.7(1C, 44.7(1C, 24.1(1C, 22.7(1C, 21.62C
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6, 100MHz, δ ppm): 159.2(1C), 155.8(1C), 143.7(2C), 140.7(2C), 127.3 (2C), 127.0 (2C), 125.3(2C), 120.0(2C), 65.6(1C), 46.7(1C), 44.7(1C), 24.1(1C), 22.7(1C), 21.6(2C).
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12
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33846689916
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4b: yield 67, Mp 198-201 °C; HPLC-MS, m/z 363.8, calculated for C20H21N5O2 363.4; 1H NMR (DMSO-d6, 400MHz, δ ppm, 8.1(d, 1H, J=8.0Hz, CONH, 7.28-7.95(m, 8H, Ar-H, 4.7(t, 1H, J=7.2Hz, NCH, 4.2-4.3(m, 3H, OCH2CH, 2.2(m, 1H, CH, 0.95(d,3H, J=6.8Hz, CH3, 0.78 (d, 3H, J=6.8Hz, CH3, 13C NMR(DMSO-d6, 100MHz, δ ppm, 162.0(1C, 155.8(1C, 143.4 (2C, 140.4(2C, 127.4(2C, 126.8(2C, 125.0(2C, 119.8(2C, 65.5(1C, 51.7(1C, 46.3(1C, 30.9 (1C, 18.62C
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6, 100MHz, δ ppm): 162.0(1C), 155.8(1C), 143.4 (2C), 140.4(2C), 127.4(2C), 126.8(2C), 125.0(2C), 119.8(2C), 65.5(1C), 51.7(1C), 46.3(1C), 30.9 (1C), 18.6(2C).
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13
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33846658791
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4c: yield 68; Mp 180-181°C; HPLC-MS, m/z 335.7, calculated for C18H17N5O2 335.3; 1H NMR (DMSO-d6, 400MHz, δ ppm, 8.05(d, 1H, J=6.4Hz, CONH, 7.30-7.90(m, 8H, Ar-H, 5.0(m, 1H, NCH, 4.33-4.22(m, 3H, OCH2CH, 1.5(d, 3H, J=6.8Hz, CH3, 13C NMR(DMSO-d6, 100MHz, δ ppm, 158.5(1C, 155.3(1C, 143.4(2C, 140.4(2C, 127.4(2C, 126.8(2C, 125.0 (2C),119.8(2C, 65.4(1C, 46.3(1C, 41.7(1C),19.21C
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6, 100MHz, δ ppm): 158.5(1C), 155.3(1C), 143.4(2C), 140.4(2C), 127.4(2C), 126.8(2C), 125.0 (2C),119.8(2C), 65.4(1C), 46.3(1C), 41.7(1C),19.2(1C).
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14
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33846669448
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4d: yield 67.8, Mp 190-194°C; HPLC-MS, m/z 377.8, calculated for C20H23N5O2 1H NMR (DMSO-d6, 400MHz, δ ppm, 8.0(br, 1H, CONH, 7.28-7.89(m, 8H, Ar-H, 4.79(br, 1H, NCH, 4.30-4.21(m, 3H, OCH2CH, 2.0(m, 1H, NCCH, 1.16-1.23(m, 2H, NCCCH2; 0.840.94(t, 3H, J=7.2Hz, NCCCCH3, 0.70-0.72(d, 3H, J=6.4Hz, NCCCH3, 13C NMR(DMSO-d6, 100 MHz, δ ppm, 167.0(1C, 156.0(1C, 143.8(2C, 140.7(2C, 127.6(2C, 127.0(2C, 125.3(2C, 120.1(2C, 65.7(1C, 65.0(1C, 46.6(1C, 30.0(1C, 18.7(1C, 13.6 (1C, 10.81C
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6, 100 MHz, δ ppm): 167.0(1C), 156.0(1C), 143.8(2C), 140.7(2C), 127.6(2C), 127.0(2C), 125.3(2C), 120.1(2C), 65.7(1C), 65.0(1C), 46.6(1C), 30.0(1C), 18.7(1C), 13.6 (1C), 10.8(1C).
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15
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33846685567
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4e: yield 80, Mp 278-280°C; HPLC-MS, m/z 412.6, calculated for C24H21N5O2 411.4; 1H NMR (DMSO-d6, 400MHz, δ ppm, 7.95(br, 1H, CONH, 7.14-7.88(m, 13H, Ar-H, 5.27(br, 1H, NCH, 4.0-4.1(m, 3H, OCH2CH, 3.24-3.21(d, 2H, J=12.8Hz, CH2, 13C NMR (DMSO-d 6, 100 MHz, δ ppm, 162.0(1C, 155.5(1C, 143.8(1C, 143.7(2C, 140.6(2C, 138.2(1C, 129.5 (1C, 127.9(1C, 127.6(2C, 127.0(2C, 126.1(1C, 125.4(1C, 125.3(2C, 120.0(2C, 65.7 (1C, 48.7(1C, 46.6(1C, 14.11C
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6, 100 MHz, δ ppm): 162.0(1C), 155.5(1C), 143.8(1C), 143.7(2C), 140.6(2C), 138.2(1C), 129.5 (1C), 127.9(1C), 127.6(2C), 127.0(2C), 126.1(1C), 125.4(1C), 125.3(2C), 120.0(2C), 65.7 (1C), 48.7(1C), 46.6(1C), 14.1(1C).
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