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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

Inactive Publication Date: 2017-05-31
HENAN UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most of the aldehydes or ketones used to construct thiosemicarbazone molecules are common benzenes or heterocyclic aromatic aldehydes and ketones, while quinoline aldehydes, especially thiosemicarbazones formed by fluoroquinolinone aldehydes, are currently Not yet reported

Method used

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  • Pefloxacin aldehyde aminothiourea derivative as well as preparation method and application thereof
  • Pefloxacin aldehyde aminothiourea derivative as well as preparation method and application thereof
  • Pefloxacin aldehyde aminothiourea derivative as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

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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Abstract

The invention discloses a pefloxacin aldehyde aminothiourea derivative as well as a preparation method and an application thereof. The following general chemical formula is as shown in the specification, wherein in the formula, R is hydrogen atom, or alkyl or cyclopropyl with 1-5 carbon atoms. The pefloxacin aldehyde aminothiourea derivative combines three advantageous pharmacophores including fluoroquinolone skeleton, Schiff base imine and thiourea, thus improving the anti-tumor activity of new compounds, reducing the toxic or side effect on normal cells, and being capable of being used as an anti-tumor activity material for developing brand-new anti-tumor medicaments.

Description

technical field [0001] The invention belongs to the technical field of new drug discovery and innovative drug synthesis, and specifically relates to a pefloxacin aldehyde thiosemicarbazone derivative, and also relates to a preparation method of the pefloxacin aldehyde thiosemicarbazone derivative, and Its application in antineoplastic drugs. Background technique [0002] The innovation of new drugs originates from the discovery of leads, and the construction of lead molecules based on the combination of dominant pharmacophore skeletons is the most economical and effective strategy. The thiosemicarbazone derivatives constructed from aldehydes or ketones and thiosemicarbazides have attracted much attention because they are easy to form complexes or chelate with macromolecules or metal ions, and exhibit a wide range of pharmacological activities. However, most of the aldehydes or ketones used to construct thiosemicarbazone molecules are common benzenes or heterocyclic aromatic...

Claims

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Application Information

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IPC IPC(8): C07D215/38A61P35/00A61P35/02
CPCC07D215/38
Inventor 袁琦张维瑞杨彤汪学猛王娜沈睿智胡国强
Owner HENAN UNIVERSITY
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