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Preparation and application of bis-fluoroquinolone thiadiazole urea N-methyl enoxacin derivatives

A technology of fluoroquinolone thiadizuron and methyl enoxacin, which is applied to the preparation of such derivatives and the application of antineoplastic drugs, bis-fluoroquinolone thiadizuron N-methyl enoxa Design Fields of Star Derivatives

Pending Publication Date: 2019-05-17
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented inventors have developed novel compounds that are structural analogs for certain types of cancer cells called Tyro3 or Kirsten Rat Cell Lymphoma (KRL). These structures include an active ingredient known as bifluoquinoimide which helps them move through blood vessels around tumours more effectively than other substances like chemotherapy agents. By linking this modified version of BFQI into specific chemical groups, these medicines may reduce their side reactions while still working properly at targeting tissue areas where they work well. Overall, it provides technical benefits over existing therapies such as chemotherapeutics and radiation treatments.

Problems solved by technology

This patented problem addressed by this patents relates to finding novel ways to chemically modify certain metabolites involved in cancer cell growth processes without affecting others' biological functions. These modifications could potentially provide potential treatments against various forms of neoplastic disease like breast cancer.

Method used

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  • Preparation and application of bis-fluoroquinolone thiadiazole urea N-methyl enoxacin derivatives
  • Preparation and application of bis-fluoroquinolone thiadiazole urea N-methyl enoxacin derivatives
  • Preparation and application of bis-fluoroquinolone thiadiazole urea N-methyl enoxacin derivatives

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Experimental program
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Effect test

Embodiment 1

[0033] 1-{2-[1-Ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-[1,8]naphthyridin-4(1H)-one-3-yl]- 1,3,4-Thiadiazol-5-yl}-3-[6-fluoro-7-(4-methylpiperazin-1-yl)-8,1-(1,3-oxopropyl) -quinoline-4(1H)-ketone-3-yl]-urea (I-1), its chemical structural formula is:

[0034]

[0035] The preparation method of the bis-fluoroquinolone thiadizuron of the present embodiment is: get ofloxacin hydroxamic acid (1 ") 1.0g (2.7mmol) and suspend in 25mL acetonitrile, add carbonyldiimidazole (CDI) 0.79g (4.9mmol), stirring at normal temperature until the material dissolves. Then add N-methyl enoxacin C-3 thiadiazole amine IV intermediate 1.05g (2.7mmol), stir in a water bath at 55~60°C for 17 hours.Stand overnight, The resulting solid was collected by filtration and washed with acetonitrile. The crude product was recrystallized from a mixed solvent of DMF-ethanol to obtain a light yellow crystal (I-1), with a yield of 62%, m.p.212-214°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.54 (brs, 1H, NH), 9.46 (s,...

Embodiment 2

[0037] (S)-1-{2-[1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-[1,8]naphthyridin-4(1H)-one-3 -yl]-1,3,4-thiadiazol-5-yl}-3-[6-fluoro-7-(4-methylpiperazin-1-yl)-8,1-(1,3- Oxygen propyl)-quinolin-4(1H)-ketone-3-yl]-urea (I-1), its chemical structural formula is:

[0038]

[0039] The preparation method of the bis-fluoroquinolone thiadizuron of this embodiment is: take levofloxacin hydroxamic acid (2″) 1.0g (2.7mmol) and suspend in 25mL acetonitrile, add carbonyldiimidazole (CDI) 0.70g (4.3mmol ), stirred at room temperature until the material was dissolved. Then, 1.05 g (2.7 mmol) of N-methyl enoxacin C-3 thiadiazole amine IV intermediate was added, and stirred in a water bath at 55-60° C. for 10 hours. Placed overnight, filtered to produce The solid was washed with acetonitrile. The crude product was recrystallized from ethanol to obtain a light yellow crystal (I-2), with a yield of 45%, m.p.223-225°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.53 (brs, 1H, NH), 9.45 (s, 1H, NH), 9.2...

Embodiment 3

[0041] 1-{2-[1-Ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-[1,8]naphthyridin-4(1H)-one-3-yl]- 1,3,4-Thiadiazol-5-yl}-3-[6,7-difluoro-8,1-(1,3-oxopropyl)-quinolin-4(1H)-one-3 -Base]-urea (I-3), its chemical structural formula is:

[0042]

[0043] The preparation method of the bis-fluoroquinolone thiadiazole of the present embodiment is: take 1.0 g (3.4 mmol) of oxyfluorocarboxylic acid hydroxamic acid (3″) and suspend it in 25 mL of acetonitrile, add 0.82 g of carbonyldiimidazole (CDI) (5.1mmol), stirring at normal temperature until the material is dissolved. Then add N-methyl enoxacin C-3 thiadiazole amine IV intermediate 1.32g (3.4mmol), and stir in a water bath at 55~60°C for 20 hours. Place overnight, The resulting solid was collected by filtration and washed with acetonitrile. The crude product was recrystallized from a DMF-ethanol mixed solvent to obtain a light yellow crystal (I-3), with a yield of 67%, m.p.226-228°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 11.53 (brs, 1H, NH...

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Abstract

The invention discloses bis-fluoroquinolone thiadiazole urea N-methyl enoxacin derivatives as well as a preparation method and an application thereof. The general chemical structure formula of the derivatives is shown in the formula I as follows in the description. In the formula I, R is ethyl, cyclopropyl, fluoroethyl, an oxazine ring consisting of C-8 or a thiazine ring consisting of C-8; L is an independent Cl or F atom, 1-piperazinyl or substituted piperazine-1-yl or a nitrogen fused heterocyclic ring; X is CH, N or F-substituted C atom (F-C) or a methoxy substituted C atom (CH3O-C). The bis-fluoroquinolone thiadiazole urea N-methyl enoxacin derivatives realize organic combination of a bis-fluoroquinolone skeleton and the thiadiazole heterocyclic ring with functional urea pharmacophores, so that transition and superposition of different pharmacophores are realized, anti-tumor activity and selectivity of fluoroquinolone are increased, toxic and side effects on normal cells are reduced, and the derivatives can be taken as an anti-tumor active substance for developing anti-tumor drugs with novel structures.

Description

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Claims

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Application Information

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Owner HENAN UNIVERSITY
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