Pefloxacin aldehyde aminothiourea derivative as well as preparation method and application thereof
A technology for pefloxacin aldehyde amino reduction and star aldehyde amino reduction, which is applied in the field of new drug discovery and innovative drug synthesis
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Embodiment 1
[0039] 1-Ethyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-aldehyde thiosemicarbazone (I-1), its chemical The structural formula is:
[0040]
[0041] That is, R in formula I is an H atom.
[0042] The preparation method of this compound is: take pefloxacin aldehyde crude product (1.0g) shown in formula (IV) and be dissolved in absolute ethanol (20 milliliters), add thiosemicarbazide (0.5g, 5.5mmol), reflux reaction 10 hour, filtered while hot, and the solid was washed twice with ethanol and distilled water twice, dried, and recrystallized with a mixed solvent of DMF-ethanol (V:V=1:3) to obtain light yellow crystals of formula (I-1 ), 0.58g of the product was obtained, m.p.>250°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.54(s,1H,CH=N), 8.79(s,1H,2-H), 8.28(s,1H,NH), 8.14(s,1H,NH2 ),8.02(s,1H,NH 2 ), 7.74 (d, 1H, 5-H), 7.06 (d, 1H, 8-H), 4.46 (q, 2H, 1-NCH 2 ), 3.33(t, 4H, piperazine-H), 2.54(t, 4H, iperazine-H), 2.22(s, 3H, N-CH 3 ), 1.47(t,3H,CH 3 ); MS(m / z): ...
Embodiment 2
[0044] 1-Ethyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-aldehyde 4-methylthiosemicarbazide (I-2) , its chemical structure is:
[0045]
[0046] That is, R in formula I is a methyl group.
[0047] The preparation method of this compound is: take pefloxacin aldehyde hydrazine dithioformic acid methyl ester (1.0g, 2.4mmol) shown in the formula (VI) and be dissolved in anhydrous n-butanol (20 milliliters), add After methylamine (0.74g, 24.0mmol), the mixed reactants were refluxed for 12 hours, filtered while hot, and the solid was washed twice with ethanol and distilled water twice, dried, and washed with DMF-ethanol (V:V=1:5) The mixed solvent was recrystallized to obtain 0.43 g of a yellow crystalline product of formula (I-2), m.p.246-248°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.42 (s, 1H, CH=N), 8.76 (s, 1H, 2-H), 8.38~8.30 (m, 2H, 2×NH), 7.76 (d, 1H, 5-H), 7.04 (d,1H,8-H), 4.42(q,2H,1-NCH 2 ), 3.32(t, 4H, piperazine-H), 3.05(d, 3H, NH-CH 3 ), 2.51 (t, 4H, ...
Embodiment 3
[0049] 1-Ethyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-aldehyde 4-ethylthiosemicarbazide (I-3) , its chemical structure is:
[0050]
[0051] That is, R in formula I is ethyl.
[0052] The preparation method of this compound is: take pefloxacin aldehyde hydrazine dithioformic acid methyl ester (1.0g, 2.4mmol) shown in the formula (VI) and be dissolved in anhydrous n-butanol (20 milliliters), add After ethylamine (1.08g, 24.0mmol), the mixed reactants were refluxed for 12 hours, filtered while hot, and the solid was washed twice with ethanol and distilled water twice, dried, and washed with DMF-ethanol (V:V=1:5) The mixed solvent was recrystallized to obtain 0.48 g of a yellow crystalline product of formula (I-3), m.p.240-242°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.38 (s, 1H, CH=N), 8.75 (s, 1H, 2-H), 8.40~8.31 (m, 2H, 2×NH), 7.76 (d, 1H, 5-H), 7.05 (d,1H,8-H), 4.41(q,2H,1-NCH 2 ), 3.66~3.25(m, 6H, piperazine-Hand CH 2 ), 2.51(t, 4H, piperazine-H), 2.25(s...
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