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Pefloxacin aldolase 4-aryl thiosemicarbazides derivative and preparation method and application thereof

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

Inactive Publication Date: 2017-05-24
ZHENGZHOU UNIV OF IND TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Pefloxacin aldolase 4-aryl thiosemicarbazides derivative and preparation method and application thereof
  • Pefloxacin aldolase 4-aryl thiosemicarbazides derivative and preparation method and application thereof
  • Pefloxacin aldolase 4-aryl thiosemicarbazides derivative and preparation method and application thereof

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Experimental program
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Embodiment 1

[0036] 1-Ethyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-aldehyde 4-phenylthiosemicarbazide (I-1) , its chemical structure is:

[0037]

[0038] That is, Ar in formula I is a benzene ring.

[0039] The preparation method of this compound is: the pefloxacin aldehyde crude product (1.0g) shown in formula IV is dissolved in absolute ethanol (30 milliliters), adds the 4-phenylthiosemicarbazide (0.6g, 3.6mmol), reflux reaction for 10 hours, filtered while hot, the solid was washed twice with ethanol, washed twice with distilled water, dried, and recrystallized with a mixed solvent of DMF-ethanol (V:V=5:3) to obtain light yellow crystals According to the formula (I-1), 0.58 g of the product was obtained, with m.p.240-242°C. 1 H NMR (400MHz, DMSO-d 6 ): 11.79(s, 1H, CH=N), 9.96(s, 1H, NH), 8.94(s, 1H, 2-H), 8.42(s, 1H, NH), 7.82~7.04(m, 7H, Ph-H, 5-Hand 8-H), 4.41(q, 2H, 1-NCH 2 ), 3.25(t, 4H, piperazine-H), 2.53(t, 4H, piperazine-H), 2.26(s, 3H, N-CH 3 ), 1....

Embodiment 2

[0041] 1-Ethyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-alcetal 4-(4-methylphenyl)amino Thiourea (I-2), its chemical structural formula is:

[0042]

[0043] That is, Ar in formula I is 4-methylphenyl.

[0044]The preparation method of this compound is: the pefloxacin aldehyde crude product (1.0g) shown in formula IV is dissolved in absolute ethanol (30 milliliters), adds the 4-(4-methylphenyl) amino group shown in formula VIII Thiourea (0.6g, 3.3mmol), reflux reaction for 12 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-2), 0.53 g of the product, m.p.246-248°C. 1 H NMR (400MHz, DMSO-d 6 ): 11.74(s, 1H, CH=N), 9.89(s, 1H, NH), 8.93(s, 1H, 2-H), 8.42(s, 1H, NH), 7.82~7.03(m, 6H, Ph-H, 5-H and 8-H), 4.38(q, 2H, 1-NCH 2 ), 3.24 (t, 4H, piperazine-H), 2.53 (t, 4H, piperazine-H), 2.23, 2.26 (2s, ...

Embodiment 3

[0046] 1-Ethyl-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:

[0047]

[0048] That is, Ar in formula I is 4-methoxyphenyl.

[0049] The preparation method of this compound is: the pefloxacin aldehyde crude product (1.0g) shown in formula IV is dissolved in absolute ethanol (30 milliliters), adds 4-(4-methoxyphenyl) shown in formula VIII Thiosemicarbazide (0.7g, 3.6mmol), reflux for 8 hours, filter while hot, wash the solid twice with ethanol and distilled water twice, dry, and use DMF-ethanol (V:V=5:3) mixed solvent After recrystallization, a pale yellow crystalline compound (I-3) was obtained, 0.62 g of the product was obtained, m.p.232-234°C. 1 H NMR (400MHz, DMSO-d 6 ): 11.72(s, 1H, CH=N), 9.86(s, 1H, NH), 8.94(s, 1H, 2-H), 8.41(s, 1H, NH), 7.77~6.94(m, 6H, Ph-H, 5-H and 8-H), 4.38(q, 2H, 1-NCH 2 ), 3.78 (s,3H,OCH 3 ), 3.25(t, 4H, piperazine-H), 2.58(t, 4H,...

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Abstract

The invention discloses a pefloxacin aldolase 4-aryl thiosemicarbazides derivative. The structural formula is shown in formula I in the specification, wherein the substituent group Ar is a benzene ring, a substituted benzene ring, a pyridine ring, a furan ring or a thiofuran ring. The invention also discloses a preparation method and an application of the pefloxacin aldolase 4-aryl thiosemicarbazides derivative. The pefloxacin aldolase 4-aryl thiosemicarbazides derivative has the advantages that the three types of superior pharmacophores of tricyclic fluoroquinolone keel, imine Schiff base and thiourea are compounded, so that the anti-tumor activity of a new compound is improved, and the toxic or side effect to normal cells is decreased; the derivative can be used as an anti-tumor active substance to develop an anti-tumor drug with a new structure.

Description

technical field [0001] The invention belongs to the technical field of new drug discovery and innovative drug synthesis, and specifically relates to a pefloxacin acetal 4-aryl thiosemicarbazide derivative, a preparation method thereof, and an application thereof as an antitumor drug. 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, especiall...

Claims

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Application Information

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IPC IPC(8): C07D215/38C07D401/12C07D405/12C07D409/12A61P35/00A61P35/02
Inventor 胡国强宋丽丽梁君李阳杰张会丽
Owner ZHENGZHOU UNIV OF IND TECH
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