Novel bromophenol amino thiourea compounds and preparation, drugs, and applications thereof
A technology of bromophenol thiosemicarbazide and bromophenol amino, which is applied in the fields of bromophenol thiosemicarbazide compounds I-IV and their pharmacological activities and pharmaceutical applications, can solve the problems such as no reports of bromophenol thiosemicarbazide compounds, and achieve normal cell Low toxicity, good antitumor activity and selective effect
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Embodiment 1
[0025] Example 1: 2-(2,3-dibromo-4,5-dimethoxybenzylidene)thiosemicarbazide (2-(2,3-dibromo-4,5-dimethoxybenzylidene)hydrazinecarbothioamide, compound I ) preparation
[0026] Weigh 10mmol 2,3-dibromo-4,5-dimethoxybenzaldehyde (3.22g) and 11mmol thiosemicarbazide (1g) into a 500mL reaction flask, add 30mL ethanol (95%) and stir evenly, Add 5mL of glacial acetic acid dropwise, then reflux and stir at 65-70°C for about 10 hours, evaporate most of the ethanol under reduced pressure, add 20ml of ice water, filter to obtain a precipitate, wash the precipitate with ice water (30mL divided into three times), and recrystallize from ethanol to obtain 2-( 2,3-Dibromo-4,5-dimethoxybenzylidene)thiosemicarbazide, white solid, yield 96%; 1 H-NMR (500MHz, DMSO- d6 )δ: 11.62(1H,s), 8.44(1H,s), 8.34(1H,s), 8.20(1H,s), 7.80(1H,s), 3.91(3H,s), 3.76(3H,s ); 13 C-NMR (125MHz, DMSO- d6 )δ: 178.5, 153.0, 148.9, 142.1, 131.2, 121.6, 117.5, 110.6, 60.7, 57.1; ESIMS: m / z 393 [M-H] — HRESIMS: calc...
Embodiment 2
[0027]Example 2: 2-(2,3,6-tribromo-4,5-dimethoxybenzylidene)thiosemicarbazide (2-(2,3,6-tribromo-4,5-dimethoxybenzylidene) hydrazinecarbothioamide, compound II)
[0028] The preparation method of compound II is similar to the preparation method of compound I, and its difference from Example 1 is that the raw material 2,3-dibromo-4,5-dimethoxybenzaldehyde is replaced by 2,3,6-tri Bromo-4,5-dimethoxybenzaldehyde, compound II was prepared as a white solid with a yield of 92%, 1 H-NMR (600MHz, DMSO- d6 )δ: 11.72(1H,s), 8.32(1H,s), 8.07(1H,s), 7.56(1H,s), 3.86(3H,s), 3.83(3H,s); 13 C-NMR (150MHz, DMSO- d6 )δ: 179.0, 152.5, 151.1, 141.8, 132.5, 122.0, 121.5, 119.5, 61.6, 61.5; ESIMS: m / z 471 [M-H] — HRESIMS: calcfor C10H10N3O2S Br3[M-H] — 471.7971, found 471.7960.
Embodiment 3
[0029] Example 3: 2-(2,3-dibromo-4,5-dihydroxybenzylidene)-N-phenylthiosemicarbazide (2-(2,3-dibromo-4,5-dihydroxybenzylidene)- N-phenylhydrazinecarbothi oamide, compound III)
[0030] The preparation method of compound III is similar to the preparation method of compound I, and its difference from Example 1 is that the raw material 2,3-dibromo-4,5-dimethoxybenzaldehyde is replaced by 2,3-dibromo- 4,5-dihydroxybenzaldehyde, compound III was prepared as a white solid with a yield of 78%, 1 H-NMR (600MHz, DMSO- d6 )δ: 11.94(1H,s), 10.16(2H,s), 10.03(1H,s), 8.50(1H,s), 7.73(1H,s), 7.60(2H,d,J=7.8Hz), 7.37(2H,dd,J=7.8,6.0Hz),7.19(1H,dd,J=7.2,7.2Hz); 13 C-NMR (150MHz, DMSO- d6 )δ: 176.4, 147.7, 145.9, 143.6, 128.7 (2C), 126.0, 125.8 (3C), 117.0, 113.8, 113.4; ESIMS: m / z 441 [M-H] — HRESIMS: calcfor C14H11N3O2SBr2[M-H] — 441.8866, found 441.8848.
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