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

A technology of methyl ciprofloxacin aldehyde and methyl ciprofloxacin hydrazide, which is applied in the field of new drug discovery and innovative drug synthesis

Inactive Publication Date: 2019-09-24
ZHENGZHOU UNIV OF IND TECH
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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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  • N-methylciprofloxacin aldehyde acetal 4-aryl thiosemicarbazide derivatives and its preparation method and application
  • N-methylciprofloxacin aldehyde acetal 4-aryl thiosemicarbazide derivatives and its preparation method and application
  • N-methylciprofloxacin aldehyde acetal 4-aryl thiosemicarbazide derivatives and its preparation method and application

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Effect test

Embodiment 1

[0037] 1-cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-aldehyde acetal 4-phenylthiosemicarbazide (I-1 ), its chemical structure is:

[0038]

[0039] That is, Ar in formula I is a benzene ring.

[0040] The preparation method of this compound is: the N-methylciprofloxacin aldehyde crude product (1.0g) shown in formula IV is dissolved in dehydrated alcohol (30 milliliters), adds the 4-phenylthiosemicarbazide shown in formula VIII ( 0.6g, 3.6mmol), reflux reaction for 10 hours, filtered while hot, the solid was washed twice with ethanol and distilled water twice, dried, and recrystallized with DMF-ethanol (V:V=5:3) mixed solvent to obtain Pale yellow crystal formula (I-1), 0.63g of the product was obtained, m.p.>250°C. 1 H NMR (400MHz, DMSO-d 6 ): 11.74(s, 1H, CH=N), 10.08(s, 1H, NH), 8.76(s, 1H, 2-H), 8.44(s, 1H, NH), 7.78~7.16(m, 7H, Ph-H, 5-H and 8-H), 3.69(m, 2H, 1-N-CH), 3.25(t, 4H, piperazine-H), 2.55(t, 4H, piperazine-H), 2.26( s, 3H, N-CH ...

Embodiment 2

[0042] 1-cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-aldehyde acetal 4-(4-methylphenyl) Thiosemicarbazide (I-2), its chemical structural formula is:

[0043]

[0044]That is, Ar in formula I is 4-methylphenyl.

[0045] The preparation method of this compound is: N-methyl ciprofloxacin aldehyde crude product (1.0g) shown in formula IV is dissolved in absolute ethanol (30 milliliters), adds 4-(4-methylbenzene shown in formula VIII Base) thiosemicarbazide (0.6g, 3.3mmol), reflux for 12 hours, filter while hot, wash the solid twice with ethanol and distilled water twice, dry, and wash with DMF-ethanol (V:V=5:3) The mixed solvent was recrystallized to obtain the light yellow crystal formula (I-2), 0.53 g of the product, m.p.248-250°C. 1 H NMR (400MHz, DMSO-d 6 ): 11.76(s, 1H, CH=N), 10.06(s, 1H, NH), 8.76(s, 1H, 2-H), 8.44(s, 1H, NH), 7.78~7.26(m, 6H, Ph-H, 5-H and 8-H), 3.69(m, 2H, 1-N-CH), 3.25(t, 4H, piperazine-H), 2.55(t, 4H, piperazine-H), 2.32...

Embodiment 3

[0047] 1-cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-aldehyde acetal 4-(4-methoxyphenyl ) thiosemicarbazide (I-3), its chemical structural formula is:

[0048]

[0049] That is, Ar in formula I is 4-methoxyphenyl.

[0050] The preparation method of this compound is: N-methyl ciprofloxacin aldehyde crude product (1.0g) shown in formula IV is dissolved in dehydrated alcohol (30 milliliters), adds 4-(4-methoxyl group shown in formula VIII Phenyl)thiosemicarbazide (0.7g, 3.6mmol), reflux reaction for 8 hours, filtered while hot, the solid was washed twice with ethanol and distilled water twice, dried, and washed with DMF-ethanol (V:V=5:3 ) mixed solvent recrystallization to obtain light yellow crystal formula (I-3), the product 0.72g, m.p.>250 ℃. 1 H NMR (400MHz, DMSO-d 6 ): 11.78(s, 1H, CH=N), 9.97(s, 1H, NH), 8.76(s, 1H, 2-H), 8.42(s, 1H, NH), 7.77~6.92(m, 6H, Ph-H, 5-H and 8-H), 3.77(s, 3H, OCH 3 ), 3.70(m, 2H, 1-N-CH), 3.26(t, 4H, piperazine-H...

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Abstract

The invention discloses N-methyl ciprofloxacin aldolase 4-aryl thiosemicarbazide derivative. A chemical structural formula of the N-methyl ciprofloxacin aldolase 4-aryl thiosemicarbazide derivative is shown in the specification, wherein a substituent group Ar is a benzene ring, a substituent benzene ring, a pyridine ring, a furan ring or a thiophene ring. The invention further discloses a preparation method and application of the N-methyl ciprofloxacin aldolase 4-aryl thiosemicarbazide derivative. The N-methyl ciprofloxacin aldolase 4-aryl thiosemicarbazide derivative disclosed by the invention achieves combination of three kinds of advantageous pharmacophore of fluoroquinolone keel, Schiff base imine and thiourea, so that antineoplastic activity of the new compound is improved, toxic and side effects on normal cells are reduced, and the N-methyl ciprofloxacin aldolase 4-aryl thiosemicarbazide derivative can serve as an antineoplastic activity material to develop antineoplastic medicine of a full-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 an N-methylciprofloxacin acetal 4-aryl thiosemicarbazide derivative, its preparation method, 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 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): C07D215/38C07D401/12C07D405/12C07D409/12A61K31/496A61P35/00A61P35/02
Inventor 胡国强郝东山张杨李书平宋丽丽
Owner ZHENGZHOU UNIV OF IND TECH
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