M. Alomari, et al.
BioorganicChemistry92(2019)103235
7.25–7.24 (m, 4H), 7.19 (dd, J = 8.0, 2.0 Hz, 1H), 7.14 (d, J = 8.0 Hz,
2H), 6.40 (s, 1H); 13C NMR (150 MHz, DMSO‑d6): δ 164.8 (C), 164.5
(C), 164.5 (C), 160.6 (C), 160.6 (C), 160.4 (C), 152.8 (C), 152.8 (C),
140.9 (C), 134.2 (C), 133.9 (CH), 133.9 (CH), 133.1 (C), 132.2 (CH),
132.2 (CH), 131.3 (CH), 128.6 (CH), 128.2 (CH), 128.2 (CH), 124.3
(CH), 124.3 (CH), 123.6 (CH), 123.6 (CH), 121.9 (C), 121.5 (CH), 121.5
(CH), 116.3 (C), 116.3 (C), 115.7 (CH), 115.7 (CH), 106.1 (C), 106.1
3.2.6. 3,3′-((4-((5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl)amino)
phenyl)methylene)bis(4-hydroxy-2H-chromen-2-one)
Yield: 79%. 1H NMR (500 MHz, DMSO‑d6) δ 9.49 (s, 1H), 9.42 (s,
1H), 7.84 (d, J = 7.7 Hz, 2H), 7.54–7.49 (m, 1H), 7.32 (d, J = 8.6 Hz,
1H), 7.25 (dd, J = 16.7, 8.0 Hz, 2H), 7.06 (d, J = 8.2 Hz, 2H), 6.88 (d,
J = 8.9 Hz, 2H), 6.26 (s, 1H), 3.74 (s, 3H); 13C NMR (150 MHz,
DMSO‑d6): δ 164.3 (C), 163.5 (C), 163.5 (C), 162.5 (C), 161.3 (C),
159.6 (C), 159.6 (C), 151.8 (C), 151.8 (C), 139.9 (C), 132.9 (C), 131.2
(CH), 131.2 (CH), 127.7 (CH), 127.7 (CH), 127.2 (CH), 127.2 (CH),
126.4 (C), 123.3 (CH), 123.3 (CH), 122.7 (CH), 122.7 (CH), 120.5 (CH),
120.5 (CH), 115.3 (C), 115.3 (C), 114.7 (CH), 114.7 (CH), 113.9 (CH),
113.9 (CH), 105.1 (C), 105.1 (C), 54.4 (OCH3), 32.7 (CH); HR-EI-MS:
m/z calcd for C34H23N3O7S, [M]+617.0312; Found 617.0311.
(C), 33.7 (CH); HR-EI-MS: m/z calcd for
C33H20BrN3O6S,
[M]+665.0256; Found 665.0241.
3.2.2. 3,3′-((4-((5-(3-bromophenyl)-1,3,4-thiadiazol-2-yl)amino)phenyl)
methylene)bis(4-hydroxy-2H-chromen-2-one)
Yield: (0.560 g 84%);1H NMR (500 MHz, DMSO‑d6) δ 9.78 (s, 1H),
9.64 (s,2H), 7.84–7.81 (m, 3H), 7.70–7.67 (m, 2H), 7.50 (d, J = 6.5 Hz,
1H), 7.32–7.27 (m, 8H), 7.12 (d, J = 8.0 Hz, 2H), 6.21 (s, 1H); 13C NMR
(150 MHz, DMSO‑d6): δ 164.5 (C), 164.5 (C), 163.2 (C), 163.2 (C),
160.6 (C), 160.6 (C), 152.8 (C), 152.8 (C), 140.9 (C), 133.9 (C), 133.8
(C), 132.2 (CH), 132.2 (CH), 132.1 (C), 130.8 (C), 128.2 (CH), 128.2
(CH), 127.9 (CH), 125.3 (CH), 124.3 (CH), 124.3 (CH), 123.6 (CH),
123.6 (CH), 122.7 (C), 121.5 (CH), 121.5 (CH), 116.3 (CH), 116.3 (CH),
115.7 (CH), 115.7 (CH), 106.1 (C), 106.1 (C), 33.7 (CH); HR-EI-MS: m/
z calcd for C33H20BrN3O6S, [M]+ 665.0256; Found 665.0240.
3.2.7. 3,3′-((4-((5-(2-fluorophenyl)-1,3,4-thiadiazol-2-yl)amino)phenyl)
methylene)bis(4-hydroxy-2H-chromen-2-one)
Yield: 80%. 1H NMR (500 MHz, DMSO‑d6) δ 9.85 (s, 2H), 9.31 (s,
1H), 7.84 (dd, J = 7.8, 1.3 Hz, 2H), 7.64 (t, J = 7.9 Hz, 1H), 7.51 (m,
2H), 7.25 (ddd, J = 19.9, 9.8, 5.7 Hz, 8H), 7.15 (ddd, J = 8.5, 5.5,
3.2 Hz, 1H), 7.08 (d, J = 8.0 Hz, 2H), 6.27 (s, 1H); 13C NMR (150 MHz,
DMSO‑d6): δ 164.8 (C), 164.5 (C), 164.5 (C), 161.6 (C), 160.6 (C),
160.6 (C), 159.3 (C), 152.8 (C), 152.8 (C), 140.9 (C), 133.9 (C), 133.1
(CH), 132.2 (CH), 132.2 (CH), 128.5 (CH), 128.2 (CH), 128.2 (CH),
124.3 (CH), 124.3 (CH), 123.6 (CH), 123.6 (CH), 123.6 (CH), 121.5
(CH), 121.5 (CH), 119.3 (C), 116.3 (C), 116.3 (C), 115.7 (CH), 115.7
(CH), 115.4 (CH), 106.1 (C), 106.1 (C), 33.7 (CH); HR-EI-MS: m/z calcd
for C33H20FN3O6S, [M]+605.0142; Found 605.0140.
3.2.3. 3,3′-((4-((5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl)amino)phenyl)
methylene)bis(4-hydroxy-2H-chromen-2-one)
Yield: (0.506 g 76%);1H NMR (500 MHz, DMSO‑d6) δ 9.70 (s,1H),
9.64 (s, 2H), 7.83 (d, J = 8.0 Hz, 2H), 7.52 (d, J = 8.0 Hz, 2H),
7.47–7.45 (m, 4H), 7.31–7.28 (m, 6H), 7.07 (d, J = 8.0 Hz, 2H), 6.22
(s, 1H);13C NMR (150 MHz, DMSO‑d6): δ 165.2 (C), 164.5 (C), 164.5
(C), 163.5 (C), 160.6 (C), 160.6 (C), 152.8 (C), 152.8 (C), 140.9 (C),
133.9 (C), 133.9 (C), 132.2 (CH), 132.2 (CH), 131.7 (CH), 131.7 (CH),
130.5 (CH), 129.7 (CH), 129.7 (CH), 128.2 (CH), 127.1 (CH), 127.1
(CH), 124.3 (CH), 124.3 (CH), 123.6 (CH), 123.6 (CH), 121.5 (C), 116.3
(C), 116.3 (C), 115.7 (CH), 115.7 (CH), 106.1 (C), 106.1 (C), 33.7 (CH);
3.2.8. 3,3′-((4-((5-(3-fluorophenyl)-1,3,4-thiadiazol-2-yl)amino)phenyl)
methylene)bis(4-hydroxy-2H-chromen-2-one)
Yield: 83%. 1H NMR (500 MHz, DMSO‑d6) δ 9.82 (s, 2H), 9.75 (s,
1H),7.82 (d, J = 8.0 Hz, 2H), 7.58–7.53 (m, 3H), 7.42 (t, J = 6.5 Hz,
1H), 7.38–7.34 (m, 1H), 7.22 (d, J = 6.6 Hz, 7H), 6.92 (t, J = 8.1 Hz,
1H), 6.27 (s, 1H);13C NMR (150 MHz, DMSO‑d6): δ 164.8 (C), 164.5 (C),
164.5 (C), 161.6 (C), 160.6 (C), 160.6 (C), 159.3 (C), 152.8 (C), 152.8
(C), 140.9 (C), 133.9 (C), 133.1 (CH), 132.2 (CH), 132.2 (CH), 128.5
(CH), 128.2 (CH), 128.2 (CH), 124.3 (CH), 124.3 (CH), 123.6 (CH),
123.6 (CH), 123.6 (CH), 121.5 (CH), 121.5 (CH), 119.3 (C), 116.3 (C),
116.3 (C), 115.7 (CH), 115.7 (CH), 115.4 (CH), 106.1 (C), 106.1 (C),
33.7 (CH); HR-EI-MS: m/z calcd for C33H20FN3O6S, [M]+605.0232;
Found 605.0230;
HR-EI-MS: m/z calcd for
C
33H20BrN3O6S, [M]+665.0256; Found
665.0238.
3.2.4. 3,3′-((4-((5-(2-methoxyphenyl)-1,3,4-thiadiazol-2-yl)amino)
phenyl)methylene)bis(4-hydroxy-2H-chromen-2-one)
Yield: (0.481 g, 78%);1H NMR (500 MHz, DMSO‑d6) δ 9.8 (s, 2H),
9.05(s,1H), 8.09 (dd, J = 8.0, 2.0 Hz, 1H), 7.87 (d, J = 8.0, Hz, 2H),
7.54 (t,J = 7.0, Hz, 2H), 7.34–7.24 (m, 6H), 7.17–7.12 (m, 3H), 7.08
(d, J = 8.0 Hz, 1H), 6.91 (t, J = 8.0 Hz, 1H), 6.26 (s, 1H), 3.89 (s, 3H);
13C NMR (150 MHz, DMSO‑d6): δ 163.3 (C), 163.3 (C), 163.1 (C), 159.4
(C), 159.4 (C), 155.6 (C), 154.4 (C), 151.6 (C), 151.6 (C), 139.7 (C),
132.7 (C), 131.0 (CH), 131.0 (CH), 131.0 (CH), 128.1 (CH), 127.0 (CH),
127.0 (CH), 123.1 (CH), 123.1 (CH), 122.5 (CH), 122.5 (CH), 122.1 (C),
120.3 (CH), 120.3 (CH), 118.8 (CH), 115.1 (C), 115.1 (C), 114.5 (CH),
114.5 (CH), 109.9 (CH), 104.9 (C), 104.9 (C), 54.5 (OCH3), 32.5 (CH);
3.2.9. 3,3′-((4-((5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl)amino)phenyl)
methylene)bis(4-hydroxy-2H-chromen-2-one)
Yield: 78%. 1H NMR (500 MHz, DMSO‑d6) δ 9.67 (s, 2H), 9.57 (s,
1H), 7.83 (dd, J = 7.8, 1.0 Hz, 2H), 7.54–7.48 (m, 2H), 7.46 (dd,
J = 8.8, 5.0 Hz, 2H), 7.25 (dd, J = 16.8, 8.2 Hz, 6H), 7.13 (t,
J = 8.8 Hz, 2H), 7.06 (d, J = 8.2 Hz, 2H), 6.26 (s, 1H); 13C NMR
(150 MHz, DMSO‑d6): δ165.2 (C), 164.6 (C), 164.6 (C), 163.5 (C),
162.7 (C), 160.6 (C), 160.6 (C), 152.8 (C), 152.8 (C), 140.9 (C), 133.9
(C), 132.2 (CH), 132.2 (CH), 129.0 (CH), 129.0 (CH), 128.3 (C), 128.2
(CH), 128.2 (CH), 124.3 (CH), 124.3 (CH), 123.6 (CH), 123.6 (CH),
121.5 (CH), 121.5 (CH), 116.5 (C), 116.5 (C), 116.3 (CH), 116.3 (CH),
115.7 (CH), 115.7 (CH), 106.1 (C), 106.1 (C), 33.7 (CH); HR-EI-MS: m/
z calcd for C33H20FN3O6S, [M]+605.0243; Found 605.0241; Anal.
Calcd: C, 65.45; H, 3.33; N, 6.94; Found C, 65.43; H, 3.34; N, 6.96.
HR-EI-MS: m/z calcd for
C
34H23N3O7S, [M]+617.1257; Found
617.1239.
3.2.5. 3,3′-((4-((5-(3-methoxyphenyl)-1,3,4-thiadiazol-2-yl)amino)
phenyl)methylene)bis(4-hydroxy-2H-chromen-2-one)
Yield: 75%. 1H NMR (500 MHz, DMSO‑d6) δ 9.64 (s, 2H), 9.61 (s,
1H), 7.84 (dd, J = 7.8, 1.3 Hz, 2H), 7.51 (dt, J = 11.9, 2.5 Hz, 2H),
7.23 (ddd, J = 18.1, 16.9, 8.3 Hz, 9H), 7.07 (d, J = 8.3 Hz, 1H), 7.03
(d, J = 7.4 Hz, 1H), 6.68 (dd, J = 8.2, 2.1 Hz, 1H), 6.27 (s, 1H), 3.73 (s,
3H);13C NMR (150 MHz, DMSO‑d6): δ 165.6 (C), 164.8 (C), 164.8 (C),
163.5 (C), 160.9 (C), 160.9 (C), 160.0 (C), 153.1 (C), 153.1 (C), 141.2
(C), 134.2 (C), 133.0(CH), 132.5 (CH), 132.5 (CH), 131.0 (CH), 128.5
(CH), 128.5 (CH), 124.6 (CH), 124.6 (CH), 124.0 (CH), 124.0 (CH),
121.8 (CH), 121.8 (CH), 119.3 (C), 117.7 (CH), 116.6 (CH), 116.6 (CH),
116.0 (C), 116.0 (C), 112.5 (CH), 106.4 (C), 106.4 (C), 55.8 (OCH3),
34.0 (CH); HR-EI-MS: m/z calcd for C34H23N3O7S, [M]+617.0210;
Found 617.0212
3.2.10. 3,3′-((4-((5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl)amino)
phenyl)methylene)bis(4-hydroxy-2H-chromen-2-one)
Yield: 80%. 1H NMR (500 MHz, DMSO‑d6) δ 9.86 (s, 1H), 9.26 (s,
2H), 7.82 (d, J = 7.8, 2H), 7.62 (d, J = 8.0, 1H),7.58–7.54 (m, 3H),
7.43–7.37 (m, 8H), 7.09 (d, J = 8.0 Hz, 2H), 6.23 (s, 1H);13C NMR
(150 MHz, DMSO‑d6): δ 164.8 (C), 164.5 (C), 164.5 (C), 161.7 (C),
160.6 (C), 160.6 (C), 152.8 (C), 152.8 (C), 140.9 (C), 133.9 (C), 132.9
(C), 132.2 (CH), 132.2 (CH), 132.2 (CH), 131.8 (CH), 130.9 (CH), 130.2
(CH), 128.2 (CH), 128.2 (CH), 128.0 (C), 124.3 (CH), 124.3 (CH), 123.6
5