Molecules 2021, 26, 3249
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7.24 (d, 1H, J = 8.8 Hz), 6.46 (d, 1H, J = 9.9 Hz), 5.86 (d, 1H, J = 9.9 Hz), 5.27 (s, 2H), 3.96 (s,
3H), 1.53 (s, 6H); 13C NMR ((CD3)2CO, 100 MHz)
δ 167.0, 153.4, 145.5, 144.9, 144.3, 130.7,
130.3, 128.0, 127.1, 127.1, 126.5, 122.8, 122.5, 122.−4, 122.2, 121.9, 120.9, 120.7, 119.5, 117.3,
112.4, 76.6, 68.6, 51.9, 26.9; ESIMS: m/z 490 [M
[M−H]− 490.1174, found 490.1175.
−
H] , HRESIMS: calcd for C26H22N3O5ClNa
1-O-((1-(3-(hydroxymethyl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)-mollugin (20). Yield: 40%,
yellow solid, MP: 151–153 ◦C, 1H NMR (CDCl3, 400 MHz)
δ 8.22 (dd, 1H, J = 6.6, 3.1 Hz),
8.14 (dd, 1H, J = 6.5, 3.1 Hz), 8.10 (s, 1H), 7.76 (s, 1H)), 7.62 (dt, 1H, J = 8.0, 1.5 Hz), 7.51
(m, 2H), 7.46 (t, 1H, J = 7.8 Hz), 7.40 (d, 1H, J = 7.7 Hz), 6.43 (d, 1H, J = 9.9 Hz), 5.69 (d, 1H,
J = 9.9 Hz), 5.30 (s, 2H), 4.78 (s, 2H), 3.93 (s, 3H), 1.52 (s, 6H); 13C NMR (CDCl3, 100 MHz)
δ
167.7, 145.8, 145.4, 144.8, 143.4, 137.1, 130.3, 129.8, 127.9, 127.2, 127.1, 127.0, 126.8, 122.7,
122.5, 121.6, 121.1, 119.8, 119.6, 118.9, 112.4, 76.6, 69.0, 64.3, 52.5, 27.7; ESIMS: m/z 494
[M+Na]+, HRESIMS: calcd for C27H25N3O5Na [M+Na]+ 494.1686, found 494.1686.
1-O-((1-(4-(hydroxymethyl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)-mollugin (21). Yield: 40%,
yellow solid, MP: 194–196 ◦C, 1H NMR (CDCl3, 400 MHz)
δ
8.22 (dd, 1H, J = 6.2, 3.3 Hz),
8.15 (dd, 1H, J = 6.1, 3.3 Hz), 8.08 (s, 1H), 7.71 (d, 2H, J = 8.0 Hz), 7.52 (m, 4H), 6.43 (d, 1H,
J = 9.9 Hz), 5.70 (d, 1H, J = 9.9 Hz), 5.32 (s, 2H), 4.77 (s, 2H), 3.94 (s, 3H), 1.52 (s, 6H); 13
NMR (CDCl3, 100 MHz) 167.7, 145.8, 145.4, 144.9, 141.9, 136.2, 130.3, 128.1, 127.9, 127.2,
C
δ
127.1, 126.8, 122.7, 122.5, 121.5, 121.1, 120.8, 119.8, 112.4, 76.6, 69.1, 64.4, 52.5, 27.7; ESIMS:
m/z 494 [M+Na]+, HRESIMS: calcd for C27H25N3O5Na [M+Na]+ 494.1684, found 494.1686.
1-O-((1-(2-ethylphenyl)-1H-1,2,3-triazol-4-yl)methyl)-mollugin (22). Yield: 45%, yellow
solid, MP: 73–75 ◦C, 1H NMR (CDCl3, 400 MHz)
δ 8.21 (dd, 1H, J = 6.5, 3.3 Hz), 8.17 (dd,
1H, J = 6.4, 3.2 Hz), 7.76 (s, 1H), 7.52 (m, 2H), 7.47 (td, 1H, J = 7.4, 1.6 Hz), 7.47 (d, 1H,
J = 7.4 Hz), 7.34 (td, 1H, J = 7.4, 1.6 Hz), 7.47 (dd, 1H, J = 8.0, 1.6 Hz), 6.44 (d, 1H, J = 9.9Hz),
5.70 (d, 1H, J = 9.9 Hz), 5.36 (s, 2H), 3.96 (s, 3H), 2.46 (q, 2H, J = 7.6 Hz), 1.52 (s, 6H), 1.12 (t,
3H, J = 7.5 Hz); 13C NMR (CDCl3, 100 MHz)
δ 167.7, 145.7, 145.4, 143.7, 140.0, 135.9, 130.3,
130.2, 129.8, 128.1, 127.1, 127.0, 126.7, 126.4, 125.3, 122.4, 121.1, 119.9, 112.4, 76.6, 68.9, 52.5,
27.7, 24.1, 15.0; ESIMS: m/z 492 [M+Na]+, HRESIMS: calcd for C28H27N3O4Na [M+Na]+
492.1893, found 492.1894.
1-O-((1-(4-ethylphenyl)-1H-1,2,3-triazol-4-yl)methyl)-mollugin (23). Yield: 65%, yellow
solid, MP: 70–71 ◦C, 1H NMR (CDCl3, 400 MHz)
δ 8.23 (dd, 1H, J = 6.4, 3.3 Hz), 8.17 (dd,
1H, J = 6.4, 3.3 Hz), 8.06 (s, 1H), 7.65 (d, 2H, J = 8.0 Hz), 7.53 (m, 2H), 7.35 (d, 2H, J = 8.0 Hz),
6.45 (d, 1H, J = 9.9 Hz), 5.70 (d, 1H, J = 9.9 Hz), 5.33 (s, 2H), 3.95 (s, 3H), 2.72 (q, 2H,
J = 7.6 Hz), 1.53 (s, 6H), 1.28 (t, 3H, J = 7.8 Hz); 13C NMR (CDCl3, 100 MHz)
δ 167.7, 145.9,
145.4, 145.3, 144.7, 134.9, 130.3, 129.1, 127.9, 127.2, 127.1, 126.8, 122.8, 122.5, 121.6, 121.1,
120.8, 119.9, 112.4, 76.6, 69.1, 52.5, 28.5, 27.7, 15.5; ESIMS: m/z 492 [M+Na]+, HRESIMS:
calcd for C28H27N3O4Na [M+Na]+ 492.1896, found 492.1894.
1-O-((1-(4-vinylphenyl)-1H-1,2,3-triazol-4-yl)methyl)-mollugin (24). Yield: 45%, yellow
solid, MP: 67–69 ◦C, 1H NMR (CDCl3, 400 MHz)
δ 8.23 (dd, 1H, J = 6.3, 3.3 Hz), 8.17 (dd,
1H, J = 6.3, 3.3 Hz), 8.07 (s, 1H), 7.72 (d, 2H, 8.3 Hz), 7.56 (d, 2H, 8.6 Hz), 8.53 (m, 2H),
6.76 (dd, 1H, J = 17.6, 10.9 Hz), 6.44 (d, 1H, J = 9.9 Hz), 5.83 (d, 1H, J = 17.6 Hz), 5.70 (d,
1H, J = 9.9 Hz), 5.36 (d, 1H, J = 10.9 Hz), 5.34 (s, 2H), 3.95 (s, 3H), 1.53 (s, 6H); 13C NMR
(CDCl3, 100 MHz) δ 167.6, 145.8, 145.4, 145.0, 138.2, 136.3, 135.5, 130.3, 127.9, 127.5, 127.2,
127.1, 126.8, 122.8, 122.5, 121.4, 121.1, 120.7, 119.9, 115.6, 112.4, 76.6, 69.1, 52.5, 27.7; ESIMS:
m/z 490 [M+Na]+, HRESIMS: calcd for C28H25N3O4Na [M+Na]+ 490.1737, found 490.1737.
1-O-((1-(3-(methylthio)phenyl)-1H-1,2,3-triazol-4-yl)methyl)-mollugin (25). Yield: 82%,
◦
yellow solid, MP: 87–89 C, 1H NMR (CDCl3, 400 MHz)
δ 8.23 (dd, 1H, J = 6.2, 3.5 Hz), 8.16
(dd, 1H, J = 6.6, 3.1 Hz), 8.09 (s, 1H), 7.64 (t, 1H, J = 1.9 Hz), 7.53 (m, 2H), 7.44 (m, 1H), 7.40
(d, 1H, J = 7.9 Hz), 7.30 (d, 1H, J = 7.9 Hz), 6.44 (d, 1H, J = 9.9 Hz), 5.70 (d, 1H, J = 9.9 Hz),
5.33 (s, 2H), 3.94(s, 3H), 2.55 (s, 3H), 1.52 (s, 6H); 13C NMR (CDCl3, 100 MHz)
δ 167.6,
145.8, 145.4, 145.0, 141.4, 137.5, 130.3, 129.9, 127.9, 127.2, 127.1, 126.8, 126.4, 122.7, 122.5,
121.6, 121.1, 119.9, 118.0, 116.9, 112.4, 76.6, 69.0, 52.6, 27.7, 15.5; ESIMS: m/z 510 [M+Na]+,
HRESIMS: calcd for C27H25N3O4SNa [M+Na]+ 510.1454, found 510.1458.