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Ofloxacin aldehyde acetal 4-aryl thiosemicarbazide derivatives and its preparation method and application

A technology of ofloxacin aldehyde and arylamino, applied in the field of new drug discovery and innovative drug synthesis

Inactive Publication Date: 2018-11-23
ZHENGZHOU UNIV OF IND TECH
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  • Summary
  • 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 acetal 4-aryl thiosemicarbazide derivatives and its preparation method and application
  • Ofloxacin aldehyde acetal 4-aryl thiosemicarbazide derivatives and its preparation method and application
  • Ofloxacin aldehyde acetal 4-aryl thiosemicarbazide derivatives and its preparation method and application

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Embodiment 1

[0033] 6-Fluoro-7-(4-methyl-piperazin-1-yl)-1,8-(2,1-oxopropyl)-quinolin-4(1H)-one-3-aldehyde acetal 4- Thiosemicarbazide (I-1), its chemical structural formula is:

[0034]

[0035] That is, Ar in formula I is a benzene ring.

[0036] The preparation method of this compound is: the ofloxacin aldehyde crude product (1.0g) shown in formula IV is dissolved in absolute ethanol (30 milliliters), adds 4-phenylthiosemicarbazide (0.6g, 3.6 g) shown in formula VIII mmol), reflux reaction for 10 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 According to formula (I-1), 0.72 g of product was obtained, m.p.>250°C. 1 H NMR (400MHz, DMSO-d 6 ): 11.79(s, 1H, CH=N), 9.96(s, 1H, NH), 8.91(s, 1H, 2-H), 8.45(s, 1H, NH), 7.57~7.21(m, 6H, Ph-H and 5-H),4.59~4.32(m,3H,OCH 2 CH), 3.24(t, 4H, piperazine-H), 2.43(t, 4H, piperazine-H), 2.23(s, 3...

Embodiment 2

[0038] 6-Fluoro-7-(4-methyl-piperazin-1-yl)-1,8-(2,1-oxopropyl)-quinolin-4(1H)-one-3-aldehyde acetal 4- (4-methylphenyl) thiosemicarbazide (I-2), its chemical structural formula is:

[0039]

[0040] That is, Ar in formula I is 4-methylphenyl.

[0041] The preparation method of this compound is: the ofloxacin aldehyde crude product (1.0g) shown in formula IV is dissolved in absolute ethanol (30 milliliters), adds 4-(4-methylphenyl) thiosemicarbazide shown in formula VIII (0.6g, 3.3mmol), reflux reaction for 10 hours, filtered while hot, washed the solid twice with ethanol and distilled water twice, dried, and recrystallized with a mixed solvent of DMF-ethanol (V:V=5:3), The light yellow crystal formula (I-2) was obtained, and 0.67 g of the product was obtained, m.p.248-250°C. 1 H NMR (400MHz, DMSO-d 6): 11.78(s, 1H, CH=N), 9.84(s, 1H, NH), 8.92(s, 1H, 2-H), 8.46(s, 1H, NH), 8.21~7.43(m, 5H, Ph-H and 5-H),4.58~4.32(m,3H,OCH 2 CH), 3.24(t, 4H, piperazine-H), 2.44(t, 4H, ...

Embodiment 3

[0043] 6-Fluoro-7-(4-methyl-piperazin-1-yl)-1,8-(2,1-oxopropyl)-quinolin-4(1H)-one-3-aldehyde acetal 4- (4-methoxyphenyl) thiosemicarbazide (I-2), its chemical structural formula is:

[0044]

[0045] That is, Ar in formula I is 4-methoxyphenyl.

[0046] The preparation method of this compound is: the ofloxacin aldehyde crude product (1.0g) shown in formula IV is dissolved in dehydrated alcohol (30 milliliters), adds the 4-(4-methoxyphenyl) amino group shown in formula VIII Thiourea (0.7g, 3.6mmol), reflux reaction for 8 hours, filtered while hot, washed the solid twice with ethanol and distilled water twice, dried, and weighed with DMF-ethanol (V:V=5:3) mixed solvent Crystallized to obtain light yellow crystalline compound (I-3), 0.76 g of the product, m.p.>250°C. 1 H NMR (400MHz, DMSO-d 6 ): 11.73(s, 1H, CH=N), 9.86(s, 1H, NH), 8.92(s, 1H, 2-H), 8.42(s, 1H, NH), 7.45~6.94(m, 5H, Ph-H,5-H),4.58~4.31(m,3H,OCH 2 CH), 3.78(s,3H,OCH 3 ), 3.24(t, 4H, piperazine-H), 2.44(t...

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Abstract

The invention discloses ofloxacin aldehyde 4-arylthiosemicarbazone derivatives. The derivatives have a general chemical structure formula shown in the description. In the formula, the substituent Ar is a benzene ring, a substituted benzene ring, a pyridine ring, a furan ring or a thiophene ring. The invention also discloses a preparation method and use of the ofloxacin aldehyde 4-arylthiosemicarbazone derivatives. The ofloxacin aldehyde 4-arylthiosemicarbazone derivatives realize splicing of three dominant pharmacophores such as a tricyclic fluoroquinolone skeleton, Schiff base imine and thiourea so that anti-tumor activity of the novel compound is improved and toxic or side effects on normal cells are reduced. The ofloxacin aldehyde 4-arylthiosemicarbazone derivatives can be used as anti-tumor active substances to develop a novel-structure anti-tumor drug.

Description

technical field [0001] The invention belongs to the technical field of new drug discovery and innovative drug synthesis, and specifically relates to an ofloxacin acetal 4-aryl thiosemicarbazide derivative, a preparation method thereof, and an application thereof 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 heterocyclic aromatic aldehydes and ketones, while quinoline aldehydes, especially ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/06A61P35/00A61P35/02
CPCC07D498/06
Inventor 张会丽梁君张忠泉李珂胡国强
Owner ZHENGZHOU UNIV OF IND TECH
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