Ofloxacin aldehyde thiosemicarbazone derivative, and preparation method and application thereof

A kind of technology of ofloxacin aldehyde amino and star aldehyde amino, which is applied in the fields of new drug discovery and innovative drug synthesis

Inactive Publication Date: 2017-05-31
HENAN UNIVERSITY
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  • 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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  • Ofloxacin aldehyde thiosemicarbazone derivative, and preparation method and application thereof
  • Ofloxacin aldehyde thiosemicarbazone derivative, and preparation method and application thereof
  • Ofloxacin aldehyde thiosemicarbazone derivative, and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0039] 6-Fluoro-7-(4-methyl-piperazin-1-yl)-1,8-(2,1-oxopropyl)-quinolin-4(1H)-one-3-aldehyde thioamido Urea (I-1), its chemical structural formula is:

[0040]

[0041] That is, R in formula I is an H atom.

[0042] The preparation method of this compound is: take the crude product ofloxacin aldehyde shown in formula (IV) (1.0g) and dissolve in dehydrated alcohol (20 milliliters), add thiosemicarbazide (0.5g, 5.5mmol), reflux reaction 12 hours , filtered while hot, the solid was washed twice with ethanol and distilled water twice, dried, and recrystallized with a mixed solvent of DMF-ethanol (V:V=5:3) to obtain light yellow crystals of formula (I-1) The product is 0.54g, m.p.238~240℃. 1 H NMR (400MHz, DMSO-d 6)δ: 11.45(s, 1H, CH=N), 8.75(s, 1H, 2-H), 8.41(s, 1H, NH), 8.36(s, 1H, NH 2 ),8.31(s,1H,NH 2 ), 7.45(d, 1H, 5-H), 4.91~4.36(m, 3H, OCH 2 CHN), 3.24(t, 4H, piperazine-H), 2.54(t, 4H, piperazine-H), 2.26(s, 3H, N-CH 3 ), 1.43 (d,3H,CH 3 ); MS(m / z): Calcd.for C ...

Embodiment 2

[0044] 6-Fluoro-7-(4-methyl-piperazin-1-yl)-1,8-(2,1-oxopropyl)-quinolin-4(1H)-one-3-aldehyde acetal 4- Methylthiosemicarbazone (I-2), its chemical structural formula is:

[0045]

[0046] That is, R in formula I is a methyl group.

[0047] The preparation method of this compound is: take ofloxacin aldehyde hydrazine dithioformic acid methyl ester (1.0g, 2.23mmol) shown in formula (VI) and be dissolved in anhydrous n-butanol (20 milliliters), add After methylamine (0.68g, 22.0mmol), the mixed reactants were refluxed for 12 hours, filtered while hot, and the solid was washed twice with ethanol and distilled water twice, dried, and washed with DMF-ethanol (V:V=1:5) The mixed solvent was recrystallized to obtain 0.56 g of a yellow crystalline product of formula (I-2), m.p.227-229°C. 1 HNMR (400MHz, DMSO-d 6 )δ: 11.44 (s, 1H, CH=N), 8.73 (s, 1H, 2-H), 8.39 (s, 1H, NH), 8.32 (s, 1H, NH), 7.42 (d, 1H, 5 -H), 4.55~4.32(m,3H,OCH 2 CHN), 3.24(t, 4H, piperazine-H), 3.06(d, 3H, N...

Embodiment 3

[0049] 6-Fluoro-7-(4-methyl-piperazin-1-yl)-1,8-(2,1-oxopropyl)-quinolin-4(1H)-one-3-aldehyde acetal 4- Thiosemicarbazide (I-3), its chemical structural formula is:

[0050]

[0051] That is, R in formula I is ethyl.

[0052] The preparation method of this compound is: take ofloxacin aldehyde hydrazine dithioformic acid methyl ester (1.0g, 2.23mmol) shown in formula (VI) and be dissolved in anhydrous n-butanol (20 milliliters), add After ethylamine (0.99g, 22.0mmol), the mixed reactants were refluxed for 12 hours, filtered while hot, and the solid was washed twice with ethanol and distilled water twice, dried, and washed with DMF-ethanol (V:V=1:5) The mixed solvent was recrystallized to obtain 0.60 g of a yellow crystalline product of formula (I-3), m.p.221-223°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.40 (s, 1H, CH=N), 8.72 (s, 1H, 2-H), 8.42 (d, 1H, NH), 8.33 (s, 1H, NH), 7.42 (d, 1H, 5 -H), 4.56~4.36(m,3H,OCH 2 CHN), 3.63(m,2H,CH 2 ), 3.24(t, 4H, piperazine-H), 2.43(t, 4...

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Abstract

The invention discloses an ofloxacin aldehyde thiosemicarbazone derivative, and a preparation method and an application thereof. A chemical structure general formula is as shown in the specification, wherein in the formula, R represents a hydrogen atom or alkyl or cyclopropyl of 1-5 carbon atoms. The ofloxacin aldehyde thiosemicarbazone derivative disclosed by the invention realizes the fusion of three advantageous pharmacophores, namely, tricyclic fluoroquinolone skeleton, schiff base imine and thiourea, thereby improving the antineoplastic activity of a new compound and reducing the toxic and side effects to normal cells, thus the ofloxacin aldehyde thiosemicarbazone derivative can be used as an antineoplastic drug of a brand-new structure developed for antineoplastic active substance.

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 ofloxacin aldehyde thiosemicarbazone, and also relates to a preparation method of the above-mentioned derivative of ofloxacin aldehyde thiosemicarbazone. and its application in anticancer 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 heter...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/06A61P35/00A61P35/02
CPCC07D498/06
Inventor 赵芬琴张维瑞汪学猛杨彤王娜沈睿智胡国强
Owner HENAN UNIVERSITY
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