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N-methylmoxifloxacin aldehyde thiosemicarbazone derivative, and preparation method and application thereof

A technology of methylmoxifloxacin aldehyde condensate amino, methylmoxifloxacin aldehyde hydrazide dithioformic acid, application in antineoplastic drugs, N-methylmoxifloxacin aldehyde condensate thiourea derivatives The field of preparation of N-methylmoxifloxacin aldehyde thiosemicarbazone derivatives

Inactive Publication Date: 2017-05-10
HENAN UNIVERSITY
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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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  • N-methylmoxifloxacin aldehyde thiosemicarbazone derivative, and preparation method and application thereof
  • N-methylmoxifloxacin aldehyde thiosemicarbazone derivative, and preparation method and application thereof
  • N-methylmoxifloxacin aldehyde thiosemicarbazone derivative, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] 1-cyclopropyl-6-fluoro-8-methoxy-7-[(1S,6S)-2,8-diazabicyclo[4.3.0]-nonan-8-yl]-quinoline- 4(1H)-keto-3-aldehyde thiosemicarbazone (I-1), its chemical structural formula is:

[0056]

[0057] That is, R in formula I is an H atom.

[0058] The preparation method of this compound is: the N-methylmoxifloxacin C-3 aldehyde crude product (1.0g) shown in formula (V) is dissolved in dehydrated alcohol (20 milliliters), adds thiosemicarbazide (0.3g, 3.3 mmol), reflux reaction for 12 hours, filtered while hot and collected solid, the gained solid was washed 2 times with ethanol successively, washed 2 times with distilled water, dried, then with a volume ratio of 1::5 DMF-ethanol mixed solvent recrystallization, A yellow crystalline substance was obtained, the structural formula was as formula (I-1), the mass was 0.68 g, m.p.246-248°C;

[0059] 1 H NMR (400MHz, DMSO-d 6 )δ: 11.45(s, 1H, CH=N), 8.84(s, 1H, 2-H), 8.45(s, 1H, NH), 8.36(s, 1H, NH 2 ),8.33(s,1H,NH 2 ), 7.84(d...

Embodiment 2

[0061] 1-cyclopropyl-6-fluoro-8-methoxy-7-[(1S,6S)-2,8-diazabicyclo[4.3.0]-nonan-8-yl]-quinoline- 4(1H)-keto-3-aldehyde acetal 4-methylthiosemicarbazide (I-2), its chemical structural formula is:

[0062]

[0063] That is, R in formula I is a methyl group.

[0064] The preparation method of the compound is as follows: 1-cyclopropyl-6-fluoro-8-methoxy-7-[(1S,6S)-2,8-diazabicyclo[4.3 .0]-nonan-8-yl]-quinolin-4(1H)-one-3-aldehyde hydrazinodithiocarbamate 1.0g (2.33mmol) was dissolved in anhydrous n-butanol (25ml ), add methylamine (0.72g, 23.0mmol), reflux reaction for 12h, place it to cool to room temperature, filter the resulting solid, wash the resulting solid twice with ethanol, wash twice with distilled water, dry, and then use the volume ratio of Recrystallized from a 1:5 mixed solvent of DMF-ethanol to obtain light yellow crystals with a structural formula such as formula (I-2), a mass of 0.50 g, and m.p.215-217°C;

[0065] 1 H NMR (400MHz, DMSO-d 6 )δ: 11.45(s,1H,...

Embodiment 3

[0068] 1-cyclopropyl-6-fluoro-8-methoxy-7-[(1S,6S)-2,8-diazabicyclo[4.3.0]-nonan-8-yl-quinoline-4 (1H)-ketone-3-aldehyde acetalizes 4-ethylthiosemicarbazide (I-3), and its chemical structural formula is:

[0069]

[0070] That is, R in formula I is ethyl.

[0071] The preparation method of the compound is as follows: 1-cyclopropyl-6-fluoro-8-methoxy-7-[(1S,6S)-2,8-diazabicyclo[4.3 .0]-nonan-8-yl]-quinolin-4(1H)-one-3-aldehyde hydrazinodithiocarbamate 1.0g (2.33mmol) was dissolved in anhydrous n-butanol (25ml ), add ethylamine (1.05g, 23mmol), reflux reaction for 12h, place and cool to room temperature, filter the resulting solid, wash the resulting solid twice with ethanol, wash twice with distilled water, dry, and then use a volume ratio of 1 : 5 DMF-ethanol mixed solvent recrystallization, to obtain light yellow crystals, structural formula such as formula (I-3), quality is 0.56g, m.p.212~214 ℃;

[0072] 1 H NMR (400MHz, DMSO-d 6 )δ: 11.45(s,1H,CH=N),8.82(s,1H,2-H),8...

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Abstract

The invention discloses an N-methylmoxifloxacin aldehyde thiosemicarbazone derivative, and a preparation method and an application thereof. The N-methylmoxifloxacin aldehyde thiosemicarbazone derivative has a structure as shown in a general formula I in the specification. In the general formula I, R is selected from the group consisting of an H atom, or a hydrocarbyl group with 1 to 5 carbon atoms or a cyclopropyl group. The N-methylmoxifloxacin aldehyde thiosemicarbazone derivative provided by the invention realizes combination of three advantage pharmacophores like a fluoroquinolone skeleton, Schiff base imine and thiourea, thereby adding the antitumor activity of a novel compound, reducing the toxic and side effects on normal cells, and being able to be used as an antitumor active substance to develop an antitumor drug with a novel 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 N-methylmoxifloxacin aldehyde thiosemicarbazone, and also relates to a kind of N-methylmoxifloxacin aldehyde thiosemicarbazone The preparation method of the derivative, 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 ben...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61P35/00A61P35/02
CPCC07D471/04
Inventor 胡国强杨彤汪学猛王娜沈睿智
Owner HENAN UNIVERSITY
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