A kind of n-methylciprofloxacin aldehyde thiosemicarbazone derivatives and its preparation method and application

A kind of technology of methyl ciprofloxacin aldehyde amino and methyl ciprofloxacin aldehyde, which is applied to N-methyl ciprofloxacin aldehyde thiosemicarbazide derivatives, N-methyl ciprofloxacin aldehyde Preparation of thiosemicarbazone derivatives, application field in antitumor drugs

Inactive Publication Date: 2019-04-16
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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  • A kind of n-methylciprofloxacin aldehyde thiosemicarbazone derivatives and its preparation method and application
  • A kind of n-methylciprofloxacin aldehyde thiosemicarbazone derivatives and its preparation method and application
  • A kind of n-methylciprofloxacin aldehyde thiosemicarbazone derivatives and its preparation method and application

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Experimental program
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Embodiment 1

[0038] 1-cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-aldehyde thiosemicarbazone (I-1), which The chemical structural formula is:

[0039]

[0040] That is, R in formula I is an H atom.

[0041]The preparation method of this compound is: take N-methylciprofloxacin C-3 aldehyde crude product (1.0g) shown in formula (V) and dissolve in absolute ethanol (20 milliliters), add thiosemicarbazide (0.5g, 5.5 mmol), reflux reaction for 12 hours, filtered while hot, washed 2 times with ethanol, washed 2 times with distilled water, dried, recrystallized with DMF-ethanol (V:V=1:3) mixed solvent, obtained light yellow crystal formula ( I-1) Product 0.66g, m.p.256~258°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.39(s, 1H, CH=N), 8.60(s, 1H, 2-H), 8.46(s, 1H, NH), 8.32(s, 1H, NH 2 ),8.27(s,1H,NH 2 ), 7.75 (d, 1H, 5-H), 7.46 (d, 1H, 8-H), 3.70 (m, 1H, 1-N-CH), 3.24 (t, 4H, piperazine-H), 2.53 ( t,4H, piperazine-H), 2.26(s,3H, N-CH 3 ), 1.26~1.15(m,4H,CH 2 CH 2 ); M...

Embodiment 2

[0043] 1-cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-aldehyde acetal 4-methylthiosemicarbazide (I-2 ), its chemical structure is:

[0044]

[0045] That is, R in formula I is a methyl group.

[0046] The preparation method of this compound is: take N-methyl ciprofloxacin aldehyde hydrazine dithioformate methyl ester (1.0 g, 2.3 mmol) shown in (VII) and dissolve in anhydrous n-butanol (20 milliliters) After adding methylamine (0.71 g, 23.0 mmol), 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) Recrystallization from a mixed solvent to obtain 0.50 g of a yellow crystalline product of formula (I-2), m.p.243-245°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.39 (s, 1H, CH=N), 8.60 (s, 1H, 2-H), 8.47~8.32 (m, 2H, 2×NH), 7.76 (d, 1H, 5-H), 7.42 (d, 1H, 8-H), 3.69 (m, 1H, 1-N-CH), 3.67 (d, 3H, NHCH 3 ), 3.24(t, 4H, pipera...

Embodiment 3

[0048] 1-cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-aldehyde acetal 4-ethylthiosemicarbazide (I-3 ), its chemical structure is:

[0049]

[0050] That is, R in formula I is ethyl.

[0051] The preparation method of this compound is: take N-methyl ciprofloxacin aldehyde hydrazine dithioformate methyl ester (1.0 g, 2.3 mmol) shown in (VII) and dissolve in anhydrous n-butanol (20 milliliters) After adding ethylamine (1.04 g, 23.0 mmol), 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) Recrystallization from a mixed solvent to obtain 0.55 g of a yellow crystalline product of formula (I-3), m.p.238-240°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.32 (s, 1H, CH=N), 8.57 (s, 1H, 2-H), 8.48~8.32 (m, 2H, 2×NH), 7.76 (d, 1H, 5-H), 7.46 (d, 1H, 8-H), 3.68 (m, 1H, 1-N-CH), 3.64 (m, 3H, NHCH 2 ), 3.25(t, 4H, piperazine-H), 2....

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Abstract

The invention discloses N-methyl ciprofloxacin aldehyde thiosemicarbazone derivatives as well as a preparation method and application thereof. The chemical structure general formula of the derivatives is described in the description, wherein R is a hydrogen atom, or an alkyl or a cyclopropyl which has 1 to 5 carbon atoms. The N-methyl ciprofloxacin aldehyde thiosemicarbazone derivatives realize the splicing of three dominant pharmacophores, i.e. fluoroquinolone skeleton, Schiff base imine and thiourea, thus improving the antitumor activity of a new compound and reducing the toxic and side effects for normal cells; therefore, the N-methyl ciprofloxacin aldehyde thiosemicarbazone derivatives can be taken as anti-tumor active substances for developing anti-tumor drugs with brand-new structures.

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-methylciprofloxacin aldehyde thiosemicarbazone, and also relates to N-methyl ciprofloxacin aldehyde thiosemicarbazone The preparation method of 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 ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/38A61P35/00
CPCC07D215/38
Inventor 袁琦张维瑞汪学猛杨彤沈睿智王娜胡国强
Owner HENAN UNIVERSITY
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