(
1
E)-16- (1-(3-nitrophenyl)-1H-1,2,3-triazole-4-yl)methylene-5α-androstan-3β-ol-
7-one (4c) Yield 86%; yellow solid; m.p. 263-265 ℃; H NMR (400 MHz, DMSO)
1
δ 9.25 (s, 1H), 8.78 (t, J = 2.1 Hz, 1H), 8.46 (dd, J=1.3, 8.1Hz, 1H), 8.36 (dd, J=7.6,
.4Hz, 1H), 7.92 (t, J = 8.2 Hz, 1H), 7.25 (s, 1H), 4.44 (d, J = 4.7 Hz, 1H), 3.39-3.29
m, 1H), 2.96 (dd, J = 17.2, 5.3Hz, 1H), 2.37 (ddd, J = 16.3, 13.9, 2.8 Hz, 1H), 1.94-
1
(
0
1
3
.88 (m, 17H), 0.84 (s, 3H), 0.79 (s, 3H), 0.76-0.63 (m, 1H); C NMR (101 MHz,
DMSO) δ 207.9, 148.5, 144.1, 137.9, 136.9, 131.5, 126.4, 124.1, 123.4, 119.4, 115.0,
6
1
4
9.2, 53.8, 48.2, 47.3, 44.4, 38.1, 36.5, 35.3, 34.2, 31.3, 31.2, 30.8, 29.0, 28.1, 20.1,
+
4.2, 12.0; HRMS (ESI) m/z calcd for C H N O [M+H] 491.2658, found
2
8
34
4
4
91.2657.
(
E)-16- (1-(4-methoxyphenyl)-1H-1,2,3-triazole-4-yl)methylene-5α-androstan-3β-
1
ol-17 -one (4d) Yield 83%; white solid; m.p. 280-282 ℃; H NMR (400 MHz, DMSO)
δ 8.90 (s, 1H), 7.83 (d, J =8.9 Hz, 2H), 7.28 (s, 1H), 7.14 (d, J =8.9 Hz, 2H), 4.28 (d,
J = 4.7 Hz, 1H), 3.84 (s, 3H), 3.39-3.31 (m, 1H), 2.98 (dd, J =17.0, 5.2 Hz, 1H) , 2.35
(
ddd, J = 16.3, 12.9, 3.0 Hz, 1H), 1.90-0.88 (m, 15H), 1.49-1.40 (m, 1H), 0.85 (s, 3H),
.80 (s, 3H), 0.76-0.68 (m, 1H); C NMR (101 MHz, DMSO) δ 207.9, 159.6, 143.6,
37.2, 129.8, 123.8, 122.1, 119.8, 114.9, 69.3, 55.6, 54.0, 48.4, 47.3, 44.5, 38.6, 36.6,
1
3
0
1
3
5.4, 34.3, 31.4, 31.3, 30.7, 29.0, 28.2, 20.1, 14.2, 12.1; HRMS (ESI) m/z calcd for
+
C H N O [M+H] 476.2913, found 476.2913.
2
9
37
3
3
(
E)-16- (1-(pyridin-3-yl)-1H-1,2,3-triazole-4-yl)methylene-5α-androstan-3β-ol-17-
1
one (4e) Yield 85%; white solid; m.p. 276-278 ℃; H NMR (400 MHz, DMSO) δ
9
8
1
.20 (d, J = 2.6 Hz, 1H), 9.16 (s, 1H), 8.73 (dd, J = 4.7, 1.4 Hz, 1H), 8.39 (ddd, J =
.3, 2.6, 1.4 Hz, 1H), 7.69 (dd, J = 8.3, 4.8 Hz, 1H), 7.28 (s, 1H), 4.43 (d, J = 4.5 Hz,
H), 2.97 (dd, J = 17.1, 5.2 Hz, 1H), 2.35 (ddd, J = 16.6, 12.9, 2.9 Hz, 1H), 1.97-0.89
1
3
(m, 17H), 1.79-1.68 (m, 1H), 0.84 (s, 3H), 0.79 (s, 3H), 0.76-0.65 (m, 1H); C NMR
(101 MHz, DMSO) δ 208.0, 149.9, 144.0, 141.6, 137.8, 133.0, 128.3, 124.5, 124.2,
1
2
4
19.5, 69.2, 53.8, 48.2, 47.4, 44.4, 38.4, 36.5, 35.3, 34.2, 31.3, 31.2, 30.7, 29.0, 28.1,
+
0.1, 14.2, 12.1; HRMS (ESI) m/z calcd for C H N O [M+H] 447.2760, found
2
7
34
4
2
47.2761.
(
E)-16-(1-phenyl-1H-1,2,3-triazole-4-yl)methylene-5-androsten-3β-ol-17-one (5a)
1
Yield 85%; white solid; m.p. 305-307 ℃; H NMR (400 MHz, DMSO) δ 9.06 (s, 1H),
7
5
.95 (d, J = 7.6 Hz, 2H), 7.64 (t, J = 7.5 Hz 2H), 7.53 (t, J = 7.4 Hz 1H), 7.30 (s, 1H),
.33 (d, J = 4.9 Hz, 1H), 3.32-3.23 (m, 1H), 3.04 (dd, J = 5.4, 17.2 Hz, 1H), 2.41 (ddd,
J = 16.3, 12.9, 3.0 Hz, 1H), 2.25-2.06 (m, 3H), 1.85-1.27 (m, 11H), 1.07-0.94 (m, 5H),
1
3
0
1
3
4
.87 (s, 3H); C NMR (101 MHz, DMSO) δ 208.0, 143.8, 141.4, 137.4, 136.3, 129.9,
29.0, 124.0, 120.4, 119.9, 119.8, 69.9, 49.8, 48.5, 47.0, 42.2, 36.8, 36.3, 31.4, 31.1,
0.7, 30.4, 29.0, 19.9, 19.2, 13.9; HRMS (ESI) m/z calcd for C H N O [M+H]
44.2651, found 444.2651.
+
2
8
33
3
2
(
1
E)-16- (1-(4-fluorophenyl)-1H-1,2,3-triazole-4-yl)methylene-5-androsten-3β-ol-
7-one (5b) Yield 86%; white solid; m.p. 262-264 ℃; H NMR (400 MHz, DMSO) δ
1