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Rufloxacin aldolase 4-aryl thiosemicarbazides derivative and preparation method and application thereof

A technology of rufloxacin aldehyde and arylamino, applied in the field of innovative drug synthesis

Inactive Publication Date: 2017-05-24
ZHENGZHOU UNIV OF IND TECH
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  • Summary
  • 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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  • Rufloxacin aldolase 4-aryl thiosemicarbazides derivative and preparation method and application thereof
  • Rufloxacin aldolase 4-aryl thiosemicarbazides derivative and preparation method and application thereof
  • Rufloxacin aldolase 4-aryl thiosemicarbazides derivative and preparation method and application thereof

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preparation example Construction

[0039] 3) The preparation method of 4-aryl thiosemicarbazides is as follows:

[0040] (a) carry out condensation reaction with the aromatic amines shown in formula (V) and carbon disulfide in the mixed solvent of ethanol-ammonia water to make the arylaminodithioformic acid ammonium (VI) shown in formula (VI);

[0041] (b) condensation reaction of arylaminodithioformate ammonium (VI) shown in formula (VI) and sodium chloroacetate to obtain S-carboxymethyl arylaminodithiocarbamate sodium salt shown in formula (VII);

[0042] (c) S-carboxymethyl arylaminodithiocarbamate sodium salt shown in formula (VII) and hydrazine hydrate undergo a substitution reaction, and the 4-aryl thiosemicarbazide shown in formula (VIII) is obtained through aftertreatment kind;

[0043]

[0044] For the specific operation steps, please refer to the preparation method of the literature "Synthesis and antibacterial activity of nitrogen-containing heterocyclic aryl thiosemicarbazones" (Hou Linyan, mast...

Embodiment 1

[0050] 6-Fluoro-8,1-(thioethyl)-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-aldehyde acetal 4-phenylaminothio Urea (I-1), its chemical structural formula (I-1) is:

[0051]

[0052] That is, Ar in formula I is phenyl.

[0053] The preparation method of this compound is: the rufloxacin C-3 aldehyde crude product (1.0g) shown in formula (IV) is dissolved in dehydrated alcohol (20 milliliters), adds 4-phenylthiosemicarbazide (0.6g, 3.6 mmol) (that is, Ar in the 4-arylthiosemicarbazides shown in formula (VIII) is a phenyl group), refluxed for 12 hours, filtered while hot and collected the solid, and the gained solid was washed 2 times with ethanol and washed with distilled water successively Twice, dry, and recrystallize with a mixed solvent of DMF-ethanol with a volume ratio of 5:3 to obtain light yellow crystals with a structural formula such as formula (I-1), a mass of 0.72 g, and m.p.246 to 248°C;

[0054] 1 H NMR (400MHz, DMSO-d 6 )δ: 11.77 (s, 1H, CH=N), 9.96 (s, 1...

Embodiment 2

[0057] 6-Fluoro-8,1-(thioethyl)-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-aldehyde acetal 4-(4-methyl Base phenyl) thiosemicarbazide (I-2), its chemical structural formula (I-2) is:

[0058]

[0059] That is, Ar in formula I is 4-methylphenyl.

[0060] The preparation method of this compound is: the rufloxacin C-3 aldehyde crude product (1.0g) shown in formula (IV) is dissolved in dehydrated alcohol (20 milliliters), adds 4-(4-methylphenyl)aminosulfur Urea (0.6g, 3.3mmol) (that is, Ar in the 4-arylthiosemicarbazides shown in formula (VIII) is 4-methylphenyl), refluxed for 12 hours, filtered while hot and collected the solid, the obtained The solid was washed twice with ethanol and distilled water twice, dried, and recrystallized with a mixed solvent of DMF-ethanol with a volume ratio of 5:3 to obtain a light yellow crystal with a structural formula such as formula (I-2) and a mass of 0.63 g, m.p.223~225℃;

[0061] 1 H NMR (400MHz, DMSO-d 6 )δ: 11.76(s, 1H, CH=N)...

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Abstract

The invention discloses a Rufloxacin aldolase 4-aryl thiosemicarbazides derivative and a preparation method and an application thereof. The structural formula is shown in formula I in the specification, wherein Ar is phenyl, substituted phenyl, pyridyl, furyl or thienyl. The Rufloxacin aldolase 4-aryl thiosemicarbazides derivative has the advantages that the three types of superior pharmacophores of tricyclic fluoroquinolone keel, imine Schiff base and thiourea are compounded, so that the anti-tumor activity of a new compound is improved, and the toxic or side effect to normal cells is decreased; the derivative can be used as an anti-tumor active substance to develop an anti-tumor drug with a new structure.

Description

technical field [0001] The invention belongs to the technical field of innovative drug synthesis, specifically relates to rufloxacin aldehyde acetal 4-aryl thiosemicarbazide derivatives, and also relates to a preparation method of rufloxacin aldehyde acetal 4-aryl thiosemicarbazide derivatives , and its application in antitumor 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 aldehy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/06A61P35/00A61P35/02
CPCC07D513/06
Inventor 蔡元元李书平李阳杰胡国强刘秋伟
Owner ZHENGZHOU UNIV OF IND TECH
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