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A levofloxacin aldehyde thiosemicarbazone derivative and its preparation method and application

A technology of levofloxacin aldehyde amino and star aldehyde amino, which is applied in the fields of new drug discovery and innovative drug synthesis

Inactive Publication Date: 2018-11-30
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 levofloxacin aldehyde thiosemicarbazone derivative and its preparation method and application
  • A levofloxacin aldehyde thiosemicarbazone derivative and its preparation method and application
  • A levofloxacin aldehyde thiosemicarbazone derivative and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0046](S)-6-fluoro-7-(4-methyl-piperazin-1-yl)-1,8-(2,1-oxopropyl)-quinolin-4(1H)-one-3- Aldehydethiosemicarbazone (I-1), its chemical structural formula is:

[0047]

[0048] That is, R in formula I is an H atom.

[0049] The preparation method of this compound is: take levofloxacin aldehyde crude product (1.0g) shown in formula (IV) and dissolve in absolute ethanol (20 milliliters), add thiosemicarbazide (0.5g, 5.5mmol), reflux reaction 12 hours, while hot Filtrate, wash the solid twice with ethanol and distilled water twice, dry, and recrystallize with a mixed solvent of DMF-ethanol (V:V=5:3) to obtain a light yellow crystal formula (I-1) to obtain the product 0.48g, m.p.231~233℃. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.43(s,1H,CH=N), 8.76(s,1H,2-H), 8.44(s,1H,NH), 8.36(s,1H,NH 2 ),8.33(s,1H,NH 2 ), 7.47(d, 1H, 5-H), 4.62~4.34(m, 3H, OCH 2 CHN), 3.24(t, 4H, piperazine-H), 2.55(t, 4H, piperazine-H), 2.26(s, 3H, N-CH 3 ), 1.45 (d,3H,CH 3 ); MS(m / z): Calcd.for C 19 h 23 ...

Embodiment 2

[0051] (S)-6-fluoro-7-(4-methyl-piperazin-1-yl)-1,8-(2,1-oxopropyl)-quinolin-4(1H)-one-3- Aldehyde 4-methylthiosemicarbazide (I-2), its chemical structural formula is:

[0052]

[0053] That is, R in formula I is a methyl group.

[0054] The preparation method of this compound is: get levofloxacin aldehyde hydrazine methyl dithioformate (1.0g, 2.23mmol) shown in formula (VI) and be dissolved in anhydrous n-butanol (20 milliliters), add methylamine ( 0.68g, 22.0mmol), 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 0.33 g of a yellow crystalline product of formula (I-2), m.p.210-212°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.46 (s, 1H, CH=N), 8.77 (s, 1H, 2-H), 8.36 (s, 1H, NH), 8.35 (s, 1H, NH), 7.46 (d, 1H, 5 -H), 4.57~4.32(m,3H,OCH 2 CHN), 3.24(t, 4H, piperazine-H), 3.12(d, 3H, NH-CH 3 ), 2...

Embodiment 3

[0056] (S)-6-fluoro-7-(4-methyl-piperazin-1-yl)-1,8-(2,1-oxopropyl)-quinolin-4(1H)-one-3- Aldehyde 4-ethylthiosemicarbazide (I-3), its chemical structural formula is:

[0057]

[0058] That is, R in formula I is ethyl.

[0059] The preparation method of this compound is: get levofloxacin aldehyde hydrazine dithioformic acid methyl ester (1.0g, 2.23mmol) shown in formula (VI) and be dissolved in anhydrous n-butanol (20 milliliters), add ethylamine ( 0.90g, 20.0mmol), 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 0.48g of a yellow crystalline product of formula (I-3), m.p.204-206°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.42 (s, 1H, CH=N), 8.77 (s, 1H, 2-H), 8.43 (d, 1H, NH), 8.33 (s, 1H, NH), 7.42 (d, 1H, 5 -H), 4.57~4.33(m,3H,OCH 2 CHN), 3.58(m,2H,CH 2 ), 3.24(t, 4H, piperazine-H), 2.46(t, ...

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Abstract

The invention discloses levofloxacin aldolase thiosemicarbazide derivative and a preparation method and application thereof. A chemical structure general formula shown in the formula is adopted, wherein R is hydrogen atom and alkyl or cyclopropyl with 1-5 carbon atoms. According to the levofloxacin aldolase thiosemicarbazide derivative, splicing of advantageous pharmacophores of a chiral fluoroquinolone skeleton, schiff base imine and thiourea is achieved, so that the anti-tumor activity of a novel compound is improved, the toxic or side effect on a normal cell is reduced, and the levofloxacin aldolase thiosemicarbazide derivative can be used for developing an anti-tumor drug of a bran-new structure as an anti-tumor active material.

Description

technical field [0001] The invention belongs to the technical field of new drug discovery and innovative drug synthesis, and specifically relates to a levofloxacin aldehyde thiosemicarbazone derivative, and also relates to a preparation method of the levofloxacin aldehyde thiosemicarbazone derivative, and its application in antitumor drugs in the application. 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 het...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/06A61P35/00A61P35/02
CPCC07D498/06
Inventor 赵芬琴张维瑞杨彤汪学猛沈睿智王娜胡国强
Owner HENAN UNIVERSITY
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