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A kind of fleroxacin aldehyde thiosemicarbazone derivatives and its preparation method and application

A technology of star aldehyde amino reduction and star aldehyde hydrazine dithioformic acid, which is applied in the field of new drug discovery and innovative drug synthesis

Inactive Publication Date: 2019-08-16
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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  • A kind of fleroxacin aldehyde thiosemicarbazone derivatives and its preparation method and application
  • A kind of fleroxacin aldehyde thiosemicarbazone derivatives and its preparation method and application
  • A kind of fleroxacin aldehyde thiosemicarbazone derivatives and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0032] 1-(2-fluoroethyl)-6,8-difluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-aldehyde thiosemicarbazone (I-1), its chemical structural formula is:

[0033]

[0034] That is, the R substituent in formula I is an H atom.

[0035] The preparation method of this compound is: get the fleroxacin C-3 aldehyde crude product (1.0g) shown in formula (IV) and be dissolved in dehydrated alcohol (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=5:3) to obtain light yellow crystals of formula (I-1 ) product 0.83g, m.p.246~248℃. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.84(s,1H,CH=N), 9.88(s,1H,2-H), 8.53(s,1H,NH), 8.37(s,1H,NH 2),8.35(s,1H,NH 2 ), 7.86 (d, 1H, 5-H), 4.86 (t, 2H, FCH 2 ),4.70(t,2H,NCH 2 ), 3.36(t, 4H, piperazine-H), 2.56(t, 4H, piperazine-H), 2.34(s, 3H, N-CH 3 ), 1.55(t,3H,CH...

Embodiment 2

[0037] 1-(2-fluoroethyl)-6,8-difluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-aldehyde acetal (4- Methyl) thiosemicarbazide (I-2), its chemical structural formula is:

[0038]

[0039] That is, R in formula I is a methyl group.

[0040] The preparation method of this compound is: take fleroxacin aldehyde hydrazine dithioformic acid methyl ester (1.0g, 2.2mmol) shown in formula (VI) and be dissolved in anhydrous n-butanol (20 milliliters), add methylamine ( 0.53g, 17.0mmol), 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 reconstituted with a mixed solvent of DMF-ethanol (V:V=1:5). Crystallized to obtain 0.52 g of a yellow crystalline product of formula (I-2), m.p.235-237°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.82(s, 1H, CH=N), 9.86(s, 1H, 2-H), 8.51(s, 1H, NH), 8.37(s, 1H, NH), 8.35(s, 1H, NH ), 7.86 (d, 1H, 5-H), 4.86 (t, 2H, FCH 2 ),4.70(t,2H,NCH 2 ),3.36~3.15(...

Embodiment 3

[0042] 1-(2-fluoroethyl)-6,8-difluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-aldehyde acetal 4-ethyl Thiosemicarbazide (I-3), its chemical structural formula is:

[0043]

[0044] That is, R in formula I is ethyl.

[0045] The preparation method of this compound is: take fleroxacin aldehyde hydrazine dithioformic acid methyl ester (1.0g, 2.2mmol) shown in formula (VI) and be dissolved in anhydrous n-butanol (20 milliliters), add ethylamine ( 0.77g, 17.0mmol), 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 reconstituted with a mixed solvent of DMF-ethanol (V:V=1:5). Crystallized to obtain 0.52 g of a yellow crystalline product of formula (I-3), m.p.233-235°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.78 (s, 1H, CH=N), 9.84 (s, 1H, 2-H), 8.48 (s, 1H, NH), 8.36 (s, 1H, NH), 7.86 (d, 1H, 5 -H), 4.87(t,2H,FCH 2 ),4.68(t,2H,NCH 2 ),3.36~3.04(m,6H, piperazine-H andCH 2 ),...

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Abstract

The invention discloses a fleroxacin aldehyde thiosemicarbazone derivative and a preparation method and application thereof. A chemical structural formula adopts a formula I which is shown in the description, wherein the substituted group R is H (hydrogen) atom or hydrocarbyl or cyclopropyl with 1 to 5 carbon atoms. The fleroxacin aldehyde thiosemicarbazone derivative has the advantage that the three advantage pharmacophores of fleroxacin keel, Schiff base imine and thiourea are spliced, so that the anti-tumor activity of a new compound is increased, the toxic or side effect to normal cells is decreased, and the fleroxacin aldehyde thiosemicarbazone derivative can be used as an anti-tumor activity matter to develop an anti-tumor medicine with a fully new structure.

Description

technical field [0001] The invention belongs to the technical field of new drug discovery and innovative drug synthesis, and specifically relates to a derivative of fleroxacin aldehyde thiosemicarbazone, and also relates to a preparation method of a derivative of fleroxacin aldehyde thiosemicarbazone, and its anti-inflammatory effect. Application in tumor medicine. 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 ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/233A61P35/00A61P35/02
CPCC07D215/233
Inventor 赵芬琴张维瑞汪学猛杨彤王娜沈睿智胡国强
Owner HENAN UNIVERSITY
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