al-Oudat et al
(m, 1.5H), 11.70–11.66 (m, 1.5H), 8.33 (s, 0.5H), 8.11–8.03 1.5H), 11.56–11.50 (m, 1.5H), 8.27 (s, 0.5H), 8.11–7.97 (m,
(m, 4H), 7.83–7.75 (m, 3H), 7.64–7.55 (m, 4.5H), 7.32– 4H), 7.70–7.32 (m, 15H), 7.10–7.05 (m, 4.5H), 6.87–6.85 (m,
7.27 (m, 3H), 7.06–7.05 (m, 1.5H), 6.88–6.85 (m, 1.5H), 1.5H), 6.49–6.42 (m, 1.5H), 5.30 (s, 2H), 5.16 (s, 3H), 4.82 (s,
13
6.49–6.41 (m, 1.5H), 5.33 (s, 2H), 4.84 (s, 1H). C NMR 1H). 13C NMR (DMSO-d6): δ 182.07, 182.02, 167.97, 164.42,
(DMSO-d6): δ 182.03, 168.45, 166.87, 164.37, 163.67, 163.73, 163.56, 163.44, 163.13, 161.13, 161.04, 160.02,
163.60, 163.48, 161.15, 161.06, 157.22, 146.88, 142.95, 159.80, 157.20, 147.90, 143.84, 136.71, 132.15, 132.09,
138.03, 137.92, 132.10, 131.87, 131.67, 130.55, 129.68, 130.54, 129.08, 128.76, 128.57, 128.43, 127.90, 127.73,
129.08, 127.16, 127.01, 126.45, 105.43, 105.32, 105.09, 126.72, 126.44, 115.10, 105.41, 105.29, 105.05, 98.70, 93.59,
98.73, 93.61, 93.48, 66.63, 65.34. HRMS (ESI, m/z): calcu- 93.44, 69.33, 66.65, 65.32. HRMS (ESI, m/z): calculated for
lated for C24H17FN2O5 [M+H]+ 433.1194; found 433.1196.
C31H24N2O6 [M+H]+ 521.1707; found 521.1707.
(e, Z)-2-((5-hydroxy-4-oxo-2-phenyl-4h-chromen-
7-yl)oxy)-n′-(4-hydroxybenzylidene)acetohydrazide
(3c)
(e, Z)-n′-(4-formylbenzylidene)-2-((5-hydroxy-4-
oxo-2-phenyl-4h-chromen-7-yl)oxy)acetohydrazide
(3f)
The product was obtained as white powder. Yield (90%). 1H The product was obtained as yellow powder. Yield (57%).
NMR (DMSO-d6) (E:Z=1:0.5): δ 12.83–12.80 (m, 1.5H), 1H NMR (DMSO-d6) (E:Z=1:0.5): δ 12.84–12.81 (m, 1.5H),
11.48–11.42 (m, 1.5H), 9.96–9.93 (m, 1.5H), 8.21–8.09 11.90–11.86 (m, 1.5H), 10.04 (s, 1.5H), 8.41 (s, 0.5H),
(m, 3.5H), 7.93 (s, 1H), 7.62–7.53 (m, 7.5H), 7.06–7.05 (m, 8.11–7.97 (m, 10H), 7.62–7.57 (m, 4.5H), 7.07–7.06 (m,
1.5H), 6.87–6.82 (m, 4.5H), 6.49–6.41 (m, 1.5H), 5.28 (s, 1.5H), 6.88 (s, 1.5H), 6.50–6.45 (m, 1.5H), 5.38 (s, 2H),
2H), 4.80 (s, 1H). 13C NMR (DMSO-d6): δ 182.12, 182.07, 4.88 (s, 1H). 13C NMR (DMSO-d6): δ 192.66, 182.05,
167.90, 164.48, 163.79, 163.68, 163.55, 163.07, 161.18, 168.56, 164.38, 163.77, 163.70, 163.64, 163.51, 161.15,
161.09, 159.59, 159.37, 157.27, 157.24, 148.51, 144.50, 161.06, 157.23, 146.65, 142.70, 139.51, 139.41, 136.88,
132.22, 132.16, 130.58, 129.20, 129.15, 129.01, 128.79, 136.72, 132.13, 130.55, 129.87, 129.11, 127.66, 127.53,
126.50, 124.99, 115.75, 115.72, 105.46, 105.37, 105.34, 126.47, 105.45, 105.33, 105.10, 98.74, 93.64, 93.52, 66.62,
105.11, 98.80, 98.75, 93.66, 93.48, 66.72, 65.36. HRMS 65.38. HRMS (ESI, m/z): calculated for C25H18N2O6 [M+H]+
(ESI, m/z): calculated for C24H18N2O6 [M+H]+ 431.1237; 443.1237; found 443.1238.
found 431.1238.
(e, Z)-4-((2-(2-((5-hydroxy-4-oxo-2-phenyl-4h-
(e, Z)-2-((5-hydroxy-4-oxo-2-phenyl-4h-chromen-
7-yl)oxy)-n′-(4-methoxybenzylidene)acetohydrazide
(3d)
chromen-7-yl)oxy)acetyl)hydrazono)methyl)benzoic
acid (3g)
The product was obtained as white powder. Yield (65%). 1H
The product was obtained as yellow powder. Yield (46%). NMR (DMSO-d6) (E:Z=1:0.5): δ 12.84–12.81 (m, 1.5H),
1H NMR (DMSO-d6) (E:Z=1:0.6): δ 12.84–12.80 (m, 11.83–11.79 (m, 1.5H), 8.39 (s, 0.5H), 8.11–8.09 (m, 4H),
1.6H), 11.56–11.49 (m, 1.6H), 8.27 (s, 0.6H), 8.11–8.09 (d, 8.01–7.99 (m, 3H), 7.87–7.81 (m, 3H), 7.63–7.54 (m, 4.5H),
J=8 Hz, 3H), 7.97 (s, 1H), 7.71–7.55 (m, 8H), 7.06–7.00 7.06–7.05 (m, 1.5H), 6.87–6.86 (m, 1.5H), 6.50–6.43 (m,
13
(m, 5H), 6.87–6.84 (m, 1.6H), 6.50–6.41 (m, 1.6H), 5.30 (s, 1.5H), 5.36 (s, 2H), 4.87 (s, 1H). C NMR (DMSO-d6): δ
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2H), 4.82 (s, 1.2H), 3.80 (s, 4.8H). C NMR (DMSO-d6): 182.03, 168.46, 166.88, 164.37, 163.68, 163.60, 163.48,
δ 182.03, 167.95, 164.43, 163.74, 163.59, 163.46, 163.10, 161.16, 161.06, 157.22, 146.87, 142.95, 138.04, 137.92,
161.13, 161.04, 160.94, 160.74, 157.21, 147.97, 143.92, 132.10, 131.88, 131.67, 130.55, 129.69, 129.08, 127.17,
132.10, 130.54, 129.08, 128.76, 128.57, 126.45, 114.25, 127.01, 126.45, 105.43, 105.31, 105.10, 98.73, 93.61, 93.48,
105.42, 105.30, 105.05, 98.69, 93.60, 93.45, 66.66, 65.31, 66.63, 65.34. HRMS (ESI, m/z): calculated for C25H18N2O7
55.28. HRMS (ESI, m/z): calculated for C25H20N2O6 [M+H]+ [M+H]+ 459.1186; found 459.1183.
445.1394; found 445.1395.
(e, Z)-2-((5-hydroxy-4-oxo-2-phenyl-4h-chromen-7-
(e, Z)-n′-(4-(benzyloxy)benzylidene)-2-((5-
hydroxy-4-oxo-2-phenyl-4h-chromen-7-yl)oxy)
acetohydrazide (3e)
yl)oxy)-n′-(4-nitrobenzylidene)acetohydrazide (3h)
The product was obtained as yellow powder. Yield (89%).
1H NMR (DMSO-d6) (E:Z=1:0.5): δ 12.84–12.81 (m, 1.5H),
The product was obtained as pale yellow powder. Yield 11.97–11.94 (m, 1.5H), 8.44 (s, 0.5H), 8.30–7.97 (m, 10H),
(64%). 1H NMR (DMSO-d6) (E:Z=1:0.5): δ 12.84–12.81 (m, 7.61–7.57 (m, 4.5H), 7.06 (s, 1.5H), 6.88 (s, 1.5H), 6.50–6.45
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