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HETEROCYCLES, Vol. 94, No. 4, 2017
5α,8α-Epidioxy-17-(quinolin-4-ylmethylene)hydrazonoandrostan-3β-ol (8b). White crystals, yield:
1
64%, mp 207.5-209.6 °C; H NMR (400 MHz, CDCl3) δ (ppm) 8.98 (1H, d, J = 4.3 Hz, 2′-Ar-H), 8.89
(1H, s, C22-H), 8.73 (1H, d, J = 8.5 Hz, 5′-Ar-H), 8.18 (1H, d, J = 8.4 Hz, 8′-Ar-H), 7.78 (1H d, J = 4.8,
3′-Ar-H), 7.76 (1H, m, 6′-Ar-H),7.64 (1H, t, J = 7.6 Hz, 7′-Ar-H), 6.55 (1H, d, J = 8.4 Hz, C6-H), 6.33
(1H, d, J = 8.4 Hz, C7-H), 4.04-3.92 (1H, m, C3-αH), 2.90-2.63 (2H, m, C16-H), 1.16 (3H, s, C19-CH3),
0.94 (3H, s, C18-CH3). 13C NMR (100 MHz, CDCl3) δ (ppm) 182.5 (17-C), 155.6 (22-C), 150.1 (2′-Ar-C),
148.9(4′-Ar-C), 137.6 (10′-Ar-C), 136.3 (7-C), 130.1 (8′-Ar-C), 129.6 (6-C), 128.8 (7′-Ar-C), 127.6
(6′-Ar-C), 125.6 (5′-Ar-C), 124.5 (9′-Ar-C), 121.1 (3′-Ar-C), 82.4 (8-C), 79.0 (5-C), 71.7 (3-C), 66.14
(14-C), 51.5 (9-C), 49.1 (4-C), 46.1 (13-C), 37.0 (12-C), 34.7 (10-C), 34.3(1-C), 30.1 (2-C), 28.3 (16-C),
23.0 (15-C), 20.3 (11-C), 19.1 (18-C), 18.1 (19-C). LC-MS (ESI) m/z: 472.2 [M+H]+. HRMS (ESI) m/z
calcd for C29H33N3O3 [M+H]+ 472.2600, found 472.2589.
5α,8α-Epidioxy-17-(indol-3-ylmethylene)hydrazonoandrostan-3β-ol (8c). White crystals, yield: 57%,
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mp 187.4-189.3 °C; H NMR (400 MHz, CDCl3) δ (ppm): 8.65 (1H, s, NH), 8.62 (1H, s, 1′-Ar-H), 8.34
(1H, d, J = 7.3 Hz, C22-H), 7.72 (1H d, J = 3.6 Hz, 4′-Ar-H), 7.53 (1H, d, J = 4.8 Hz, 7′-Ar-H), 7.50 (1H,
s, 5′-Ar-H), 7.39 (1H, d, J = 7.4 Hz, 6′-Ar-H), 6.56 (1H, d, J = 8.5 Hz, C6-H), 6.31 (1H, d, J = 8.4 Hz,
C7-H), 4.03-3.94 (1H, m, C3-αH), 2.99-2.75 (2H, m, C16-H), 0.99 (3H, s, C19-CH3), 0.93(3H, s,
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C18-CH3). C NMR (100 MHz, CDCl3) δ (ppm): 180.3 (17-C), 154.4 (22-C), 136.9 (9′-Ar-C), 136.0
(7-C), 130.9 (2′-Ar-C), 129.6 (6-C), 125.1 (8′-Ar-C), 123.5 (4′-Ar-C), 122.7 (6′-Ar-C), 121.6 (5′-Ar-C),
113.8 (3′-Ar-C), 111.3 (7′-Ar-C), 82.4 (8-C), 79.2 (5-C), 71.8 (3-C), 66.3 (14-C), 51.5 (9-C), 49.2 (4-C),
45.8 (13-C), 37.2 (12-C), 34.7 (10-C), 34.1 (1-C), 30.1 (2-C), 28.2 (16-C), 27.8 (15-C), 20.3 (11-C), 19.2
(18-C), 18.1 (19-C). LC-MS (ESI) m/z: 460.3 [M+H]+. HRMS (ESI) m/z calcd for C28H33N3O3 [M+H]+:
460.2600, found 460.2596.
5α,8α-Epidioxy-17-(thiophene-3-ylmethylene)hydrazonoandrostan-3β-ol (8d). Faint yellow crystals,
yield: 59%, mp 173.8-175.2 °C; 1H NMR (400 MHz, CDCl3) δ 8.30 (1H, s, C22-H), 7.61 (1H, d, J = 1.6
Hz, 2′-Ar-H), 7.54 (1H, d, J = 4.9 Hz, 5′-Ar-H), 7.34 (1H, d, J = 2.8 Hz, 4′-Ar-H), 6.53 (1H, d, J = 8.4 Hz,
C6-H), 6.31 (1H, d, J = 8.4 Hz, C7-H), 4.04-3.89 (1H, m, C3-αH), 2.90-2.51 (2H, m, C16-H), 1.09 (3H, s,
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C19-CH3), 0.92 (1H, s, C18-CH3). C NMR (100 MHz, CDCl3) δ (ppm): 180.8 (17-C), 152.6 (22-C),
136.1 (7-C), 131.0 (3′-Ar-C), 130.1 (6-C), 128.8 (2′-Ar-C), 126.6 (5′-Ar-C), 125.5 (4′-Ar-C), 82.4 (8-C),
79.1 (5-C), 71.8 (3-C), 66.2 (14-C), 51.5 (9-C), 49.1 (4-C), 45.9 (13-C), 37.1 (12-C), 34.7 (10-C), 34.0
(1-C), 30.1 (2-C), 27.8 (16-C), 23.0 (15-C), 20.3 (11-C), 19.2 (18-C), 18.0 (19-C). LC-MS (ESI) m/z:
427.2 [M+H]+. HRMS (ESI) m/z calcd for C24H30N2O3S [M+H]+ 427.2055, found 427.2045.
5α,8α-Epidioxy-17-(furan-3-ylmethylene)hydrazonoandrostan-3β-ol (8e). Faint yellow crystals, yield:
55%, mp 165.7-168.2 °C; 1H NMR (400 MHz, CDCl3) δ 8.16 (1H, s, C22-H), 7.81-7.63 (1H, m, 2′-Ar-H),
6.81 (1H, d, J = 3.3 Hz, 4′-Ar-H), 6.52 (1H, s, 3′-Ar-H), 6.51 (1H, d, J = 3.1 Hz, C6-H), 6.32 (1H, d, J =