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

A technology of methyllomefloxacin aldehyde condensate amino and methyllomefloxacin aldehyde hydrazide dithioformic acid, which is applied in the field of new drug discovery and innovative drug synthesis

Inactive Publication Date: 2019-03-08
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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  • A kind of n-methyllomefloxacin aldehyde thiosemicarbazone derivatives and its preparation method and application
  • A kind of n-methyllomefloxacin aldehyde thiosemicarbazone derivatives and its preparation method and application
  • A kind of n-methyllomefloxacin aldehyde thiosemicarbazone derivatives and its preparation method and application

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Embodiment 1

[0036] 1-Ethyl-6,8-difluoro-7-(3,4-dimethyl-piperazin-1-yl)-quinolin-4(1H)-one-3-aldehyde thiosemicarbazone (I -1), its chemical structural formula is:

[0037]

[0038] That is, the R substituent in formula I is an H atom.

[0039] The preparation method of this compound is: N-methyl lomefloxacin aldehyde crude product (1.0g) shown in formula (V) is dissolved in dehydrated alcohol (20 milliliters), adds thiosemicarbazide (0.5g, 5.5mmol), reflux reaction 10 hours, filtered while hot, the solid was washed twice with ethanol successively, washed twice with distilled water, dried, and recrystallized with a mixed solvent of DMF-ethanol (V:V=1:3) to obtain light yellow crystals of formula (I- 1) The product is 0.66g, m.p.243~245℃. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.76(s, 1H, CH=N), 8.88(s, 1H, 2-H), 8.55(s, 1H, NH), 8.42(s, 1H, NH 2 ),8.36(s,1H,NH 2 ), 7.86(d,1H,5-H), 4.56(q,2H,CH 2 ), 3.36~2.55 (mt, 7H, piperazine-H), 2.33 (s, 3H, N-CH 3 ), 1.46~1.28(m,6H,2×CH 3 ); MS(m / z...

Embodiment 2

[0041] 1-Ethyl-6,8-difluoro-7-(3,4-dimethyl-piperazin-1-yl)-quinolin-4(1H)-one-3-aldehyde acetal 4-methylaminosulfur Urea (I-2), its chemical structural formula is:

[0042]

[0043] That is, R in formula I is a methyl group.

[0044] The preparation method of this compound is: take N-methyllomefloxacin aldehyde hydrazine dithioformate methyl ester (1.0g, 2.2mmol) shown in formula (VII) and dissolve in anhydrous n-butanol (20 milliliters) , add methylamine (0.53g, 17.0mmol) and then mix the reactants to reflux for 12 hours, filter while hot, wash the solid with ethanol twice, distilled water twice, dry, and wash with DMF-ethanol (V:V=1 :5) recrystallization from a mixed solvent to obtain 0.43 g of a yellow crystalline product of formula (I-2), m.p.241-243°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.75 (s, 1H, CH=N), 8.87 (s, 1H, 2-H), 8.46 (s, 1H, NH), 8.36 (s, 1H, NH), 7.87 (d, 1H, 5 -H), 4.56(q,2H,CH 2 ),3.56~3.37(m,7H, piperazine-H and CH 3 ), 2.56~2.48 (m, 3H, piperazine-...

Embodiment 3

[0046] 1-Ethyl-6,8-difluoro-7-(3,4-dimethyl-piperazin-1-yl)-quinolin-4(1H)-one-3-aldehyde acetal 4-ethylaminosulfur Urea (I-3), its chemical structural formula is:

[0047]

[0048] That is, R in formula I is ethyl.

[0049] The preparation method of this compound is: take N-methyllomefloxacin aldehyde hydrazine dithioformate methyl ester (1.0g, 2.2mmol) shown in formula (VII) and dissolve in anhydrous n-butanol (20 milliliters) In , 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, wash twice with distilled water, dry, and wash with DMF-ethanol (V:V=1 :5) recrystallization from a mixed solvent to obtain 0.45 g of a yellow crystalline product of formula (I-3), m.p.236-238°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.76 (s, 1H, CH=N), 8.87 (s, 1H, 2-H), 8.45 (s, 1H, NH), 8.36 (s, 1H, NH), 7.87 (d, 1H, 5 -H), 4.56(q,2H,CH 2 ),3.36~3.07(m,6H, piperazine-H and CH 2 ), 2.56~2.48 (m, 3H, piperazin...

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Abstract

The invention discloses N-methyl lomefloxacin 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; in the formula I, the substituent group R is a hydrogen atom, or an alkyl or a cyclopropyl which has 1 to 5 carbon atoms. The N-methyl lomefloxacin aldehyde thiosemicarbazone derivatives realize the splicing of three dominant pharmacophores, i.e. difluoroquinolone 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 lomefloxacin 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-methyllomefloxacin aldehyde thiosemicarbazone, and also relates to an N-methyllomefloxacin 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 benzenes o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04A61K31/496A61P35/00
CPCC07D401/04
Inventor 韩紫岩杨彤汪学猛王娜沈睿智胡国强
Owner HENAN UNIVERSITY
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