N-methyl enoxacin aldehyde acetal 4-aryl thiosemicarbazide derivatives and its preparation method and application

A technology of methylenoxacin aldehyde and methylenoxacin hydrazide, which is applied in the field of innovative drug synthesis

Inactive Publication Date: 2018-10-09
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 the thiosemicarbazones formed by nalidyridic aldehydes, especially flunalidinone aldehydes, are currently Not yet reported

Method used

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  • N-methyl enoxacin aldehyde acetal 4-aryl thiosemicarbazide derivatives and its preparation method and application
  • N-methyl enoxacin aldehyde acetal 4-aryl thiosemicarbazide derivatives and its preparation method and application
  • N-methyl enoxacin aldehyde acetal 4-aryl thiosemicarbazide derivatives and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0057] 1-Ethyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-naphthyridin-4(1H)-one-3-aldehyde acetal 4-phenylthiosemicarbazide (I-1 ), its chemical structural formula (I-1) is:

[0058]

[0059] That is, the substituent Ar in formula I is phenyl.

[0060] The preparation method of this compound is: the N-methyl enoxacin C-3 aldehyde crude product (1.0g) shown in formula (V) is dissolved in dehydrated alcohol (20 milliliters), adds 4-phenylthiosemicarbazide ( 0.6g, 3.6mmol) (that is, Ar in the 4-aryl thiosemicarbazides shown in formula (IX) is phenyl), refluxed for 10 hours, filtered while hot and collected the solid, and the gained solid was washed successively with ethanol for 2 Wash twice with distilled water, dry, and recrystallize with a mixed solvent of DMF-ethanol with a volume ratio of 5:3 to obtain a yellow crystal with a structural formula (I-1) and a mass of 0.76g, m.p.238-240°C ;

[0061] 1 H NMR (400MHz, DMSO-d 6 )δ: 11.78(s, 1H, CH=N), 10.06(s, 1H, NH), 9.16(s, 1H...

Embodiment 2

[0064] 1-Ethyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-naphthyridin-4(1H)-one-3-aldehyde acetal 4-(4-methylphenyl)amino Thiourea (I-2), its chemical structural formula (I-2) is:

[0065]

[0066] That is, Ar in formula I is 4-methylphenyl.

[0067] The preparation method of this compound is: N-methyl enoxacin C-3 aldehyde crude product (1.0g) shown in formula (V) is dissolved in dehydrated alcohol (20 milliliters), adds 4-(4-methylbenzene Base) thiosemicarbazide (0.6g, 3.3mmol) (that is, Ar in the 4-aryl thiosemicarbazides shown in formula (IX) is 4-methylphenyl), reflux reaction for 12 hours, filtered while hot and Collect the solid, wash the obtained solid twice with ethanol and distilled water twice, dry, and recrystallize with a mixed solvent of DMF-ethanol with a volume ratio of 5:3 to obtain a light yellow crystal, the structural formula of which is shown in formula (I-2) , mass is 0.68g, m.p.218~220℃;

[0068] 1 H NMR (400MHz, DMSO-d 6 )δ: 11.77(s, 1H, CH=N), 9.82(...

Embodiment 3

[0071] 1-Ethyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-naphthyridin-4(1H)-one-3-aldehyde acetal 4-(4-methoxyphenyl) Thiosemicarbazide (I-3), its chemical structural formula (I-3) is:

[0072]

[0073] That is, Ar in formula I is 4-methoxyphenyl.

[0074] The preparation method of this compound is: N-methyl enoxacin C-3 aldehyde crude product (1.0g) shown in formula (V) is dissolved in dehydrated alcohol (20 milliliters), adds 4-(4-methoxy Phenyl) thiosemicarbazide (0.7g, 3.6mmol) (that is, Ar in the 4-aryl thiosemicarbazides shown in formula (IX) is 4-methoxyphenyl), reflux reaction for 8 hours, while hot Filtrate and collect the solid, the gained solid is washed with ethanol twice, distilled water twice successively, dry, use the mixed solvent recrystallization of the DMF-ethanol that is 5:3 with the volume ratio, obtain pale yellow crystal, structural formula is as formula (I- 3), the mass is 0.64g, m.p.234~236℃;

[0075] 1 H NMR (400MHz, DMSO-d 6 )δ: 11.78(s, 1H, CH=N)...

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Abstract

The invention discloses an N-methyl enoxacin aldehyde-4-aryl thiosemicarbazide derivative, and a preparation method and application thereof. The N-methyl enoxacin aldehyde-4-aryl thiosemicarbazide derivative has a structure formula as shown in formula (1), wherein Ar is a phenyl group, a substituted phenyl group, a pyridyl group, a furan group or a thienyl group. According to the N-methyl enoxacin aldehyde-4-aryl thiosemicarbazide derivative disclosed by the invention, the combination of three advantaged pharmacophores, including fluorine naphthyridine ketone framework, Schiff base imine and thiourea can be realized, so that the anti-tumor activity of the new compound can be increased and the toxic and side effects to normal cells can be reduced. The N-methyl enoxacin aldehyde-4-aryl thiosemicarbazide derivative can be used as an anti-tumor active substance for developing an anti-tumor drug with a brand new structure.

Description

technical field [0001] The invention belongs to the technical field of innovative drug synthesis, and specifically relates to N-methylenoxacin aldehyde acetal 4-aryl thiosemicarbazide derivatives, and also relates to N-methylenoxacin aldehyde acetal 4-arylamino A preparation method of thiourea derivatives and their 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 aro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A61P35/00A61P35/02
CPCC07D471/04
Inventor 姜亚玲李阳杰李书平胡国强张会丽
Owner ZHENGZHOU UNIV OF IND TECH
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