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N-methyl gatifloxacin aldehyde thiosemicarbazone derivative and preparation method and application thereof

A technology for afloxacin aldehyde amino reduction and gatifloxacin, which is applied to the preparation of N-methyl gatifloxacin aldehyde thiosemicarbazone derivatives, N-methyl gatifloxacin aldehyde thiosemicarbazones Derivatives, the field of application in antineoplastic drugs

Inactive Publication Date: 2017-06-13
HENAN UNIVERSITY
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  • Abstract
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  • 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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  • N-methyl gatifloxacin aldehyde thiosemicarbazone derivative and preparation method and application thereof
  • N-methyl gatifloxacin aldehyde thiosemicarbazone derivative and preparation method and application thereof
  • N-methyl gatifloxacin aldehyde thiosemicarbazone derivative and preparation method and application thereof

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Experimental program
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Embodiment 1

[0033] 1-cyclopropyl-6-fluoro-7-(3,4-dimethyl-piperazin-1-yl)-8-methoxy-quinolin-4(1H)-one-3-aldehyde amino Thiourea (I-1), its chemical structural formula is:

[0034]

[0035] That is, the R substituent in formula I is an H atom.

[0036] The preparation method of this compound is: take N-methyl gatifloxacin aldehyde crude product (1.0g) shown in formula (V) and be dissolved in absolute ethanol (20 milliliters), add thiosemicarbazide (0.5g, 5.5mmol), Reflux reaction for 10 hours, filter while hot, wash twice with ethanol, wash twice with distilled water, dry, and recrystallize with DMF-ethanol (V:V=5:3) mixed solvent to obtain light yellow crystals of formula (I-1 ), to obtain product 0.53g, m.p.232~234℃. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.78(s, 1H, CH=N), 9.06(s, 1H, 2-H), 8.53(s, 1H, NH), 8.45(s, 1H, NH 2 ),8.34(s,1H,NH 2 ), 7.87(d,1H,5-H), 3.83(s,3H,OCH 3 ), 4.15 (m, 1H, CH), 3.36~2.55 (mt, 7H, piperazine-H), 2.33 (s, 3H, N-CH 3 ), 1.36~1.12(m,7H,CH 3 and CH 2 C...

Embodiment 2

[0038] 1-cyclopropyl-6-fluoro-7-(3,4-dimethyl-piperazin-1-yl)-8-methoxy-quinolin-4(1H)-one-3-aldehyde acetal 4 -Methylthiosemicarbazide (I-2), its chemical structural formula is:

[0039]

[0040] That is, R in formula I is a methyl group.

[0041] The preparation method of this compound is: take N-methyl gatifloxacin aldehyde hydrazine dithioformic acid methyl ester (1.0g, 2.1mmol) shown in formula (VI) and dissolve in anhydrous n-butanol (20 ml ), after adding 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 twice with distilled water, dried, and washed with DMF-ethanol (V:V= 1:5) mixed solvent recrystallization to obtain 0.40 g of a yellow crystal product of formula (I-2), m.p.223-225°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.76 (s, 1H, CH=N), 8.97 (s, 1H, 2-H), 8.44 (s, 1H, NH), 8.35 (s, 1H, NH), 7.88 (d, 1H, 5 -H), 4.16(m,1H,CH), 3.82(s,3H,OCH 3 ),3.53~3.36(m,7H, piperazine...

Embodiment 3

[0043] 1-cyclopropyl-6-fluoro-7-(3,4-dimethyl-piperazin-1-yl)-8-methoxy-quinolin-4(1H)-one-3-aldehyde acetal 4 - ethylthiosemicarbazide (I-3), its chemical structural formula is:

[0044]

[0045] That is, R in formula I is ethyl.

[0046] The preparation method of this compound is: take N-methyl gatifloxacin aldehyde hydrazine dithioformic acid methyl ester (1.0g, 2.1mmol) shown in formula (VI) and dissolve in anhydrous n-butanol (20 ml ), add ethylamine (0.77g, 17.0mmol) and then mix the reactants to reflux for 12 hours, filter while hot, wash the solid twice with ethanol and twice with distilled water, dry, and wash with DMF-ethanol (V:V= 1:5) mixed solvent recrystallization to obtain 0.42 g of yellow crystalline product of formula (I-3), m.p.225-227°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.78 (s, 1H, CH=N), 8.93 (s, 1H, 2-H), 8.44 (s, 1H, NH), 8.37 (s, 1H, NH), 7.88 (d, 1H, 5 -H), 4.17(m,1H,CH), 3.82(s,3H,OCH 3 ),3.36~3.14(m,6H, piperazine-Hand CH 2 ), 2.56(m,3H, piper...

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Abstract

The invention discloses N-methyl gatifloxacin aldehyde thiosemicarbazone derivative and a preparation method and application thereof. The N-methyl gatifloxacin aldehyde thiosemicarbazone derivative has a chemical structural formula as a following formula I. In the formula I, substituent R is an H atom or alkyl or cyclopropyl with 1 to 5 carbon atoms. According to the N-methyl gatifloxacin aldehyde thiosemicarbazone derivative disclosed by the invention, combination of three kinds of advantage pharmacophore of a fluoroquinolone framework, imine Schiff base, thiourea and the like is achieved; thus, antineoplastic activity of novel compound is improved, a toxic and side effect of normal cells is reduced, and the N-methyl gatifloxacin aldehyde thiosemicarbazone derivative can serve as antineoplastic activity substance to develop antineoplastic 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-methyl gatifloxacin aldehyde thiosemicarbazone, and also relates to a kind of N-methyl gatifloxacin aldehyde thiosemicarbazone A preparation method of urea 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 ...

Claims

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Application Information

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IPC IPC(8): C07D401/04A61P35/00A61P35/02
CPCC07D401/04
Inventor 胡国强汪学猛杨彤王娜沈睿智
Owner HENAN UNIVERSITY
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