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1-cyclopropyl-7-aminomethyl triazole-fluoroquinolones carboxylic acid derivative, method for preparing same and application of 1-cyclopropyl-7-aminomethyl triazole-fluoroquinolones carboxylic acid derivative

A technology of fluoroquinolone carboxylic acid and aminomethyl triazole, which is applied in the field of innovative drug synthesis to achieve the effect of overcoming drug resistance

Inactive Publication Date: 2015-08-05
HENAN UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, in order to discover new antibacterial active fluoroquinolone compounds, many studies have focused on the changes of the N-substituent of piperazine, but there are few changes in the insertion of functional linking chains between the piperazine group and the quinoline ring skeleton.

Method used

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  • 1-cyclopropyl-7-aminomethyl triazole-fluoroquinolones carboxylic acid derivative, method for preparing same and application of 1-cyclopropyl-7-aminomethyl triazole-fluoroquinolones carboxylic acid derivative
  • 1-cyclopropyl-7-aminomethyl triazole-fluoroquinolones carboxylic acid derivative, method for preparing same and application of 1-cyclopropyl-7-aminomethyl triazole-fluoroquinolones carboxylic acid derivative
  • 1-cyclopropyl-7-aminomethyl triazole-fluoroquinolones carboxylic acid derivative, method for preparing same and application of 1-cyclopropyl-7-aminomethyl triazole-fluoroquinolones carboxylic acid derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 1-cyclopropyl-6-fluoro-7-(4-dimethylaminomethyl-[1,2,3]triazol-1-yl)-quinolin-4(1H)-one-3-carboxylic acid (I-1), its chemical structural formula is:

[0043]

[0044] That is, R in formula I is dimethylamino.

[0045] The preparation method of the compound is as follows: using dimethylamine as the amine donor, according to the above-mentioned general preparation method of the target object (I), the light yellow crystal (I-1) is obtained, the yield is 75.0%, m.p.226~228°C . 1 H NMR (400MHz, DMSO-d 6 ):δ15.46(1H,brs,COOH),8.88(1H,s,2-H),8.05(d,J=13.2Hz,1H,5-H),7.86~7.82(2H,m,5- H and 5″-H), 7.64 (1H, d, J=7.2Hz, 8-H), 5.35 (s, 2H, NCH 2 ),3.68~3.54(m,1H,1′-H),2.43(s,6H,2×CH 3 ), 1.27~1.18 (m, 4H, 2′- and 3′-H); MS(m / z): Calcd.for C 18 h 18 FN 5 o 3 :371.37[M] + ;Found:372[M+H] + .

Embodiment 2

[0047] 1-cyclopropyl-6-fluoro-7-(4-diethylaminomethyl-[1,2,3]triazol-1-yl)-quinolin-4(1H)-one-3-carboxylic acid (I-2), its chemical structural formula is:

[0048]

[0049] That is, R in formula I is diethylamino.

[0050] The preparation method of the compound is: using diethylamine as the amine donor, according to the above-mentioned general preparation method of the target object (I), to obtain a light yellow crystal (I-2), the yield is 64.0%, m.p.218~220°C . 1 H NMR (400MHz, DMSO-d 6 ):δ15.47(brs,1H,COOH),8.85(s,1H,2-H),8.03(d,J=13.2Hz,1H,5-H),7.86~7.76(2H,m,5- H and 5″-H), 7.62 (1H, d, J=7.2Hz, 8-H), 5.33 (2H, s, NCH 2 ),3.68~3.57(1H,m,1′-H),2.44~2.36(m,4H,2×CH 2 ),1.34~1.17(m,10H,2′-,3′-H and 2×CH 3 ); MS(m / z): Calcd.for C 20 h 22 FN 5 o 3 :399.43[M] + ;Found:400[M+H] + .

Embodiment 3

[0052] 1-cyclopropyl-6-fluoro-7-(4-piperidin-1-methyl-[1,2,3]triazol-1-yl)-quinolin-4(1H)-one-3- Carboxylic acid (I-3), its chemical structural formula is:

[0053]

[0054] That is, R in formula I is piperidin-1-yl.

[0055] The preparation method of the compound is as follows: using piperidine as the amine donor, according to the above-mentioned general preparation method of the target object (I), the light yellow crystal (I-3) was obtained with a yield of 63.0%, m.p.225-227°C. 1 H NMR (400MHz, DMSO-d 6 ):δ15.43(brs,1H,COOH),8.86(s,1H,2-H),8.07(d,J=13.2Hz,1H,5-H),7.87~7.82(2H,m,5- H and 5″-H), 7.65 (1H, d, J = 7.2Hz, 8-H), 5.31 (s, 2H, NCH 2 ),3.66~3.58(m,1H,1′-H),3.05~2.28(m,4H,N(CH 2 ) 2 ),1.63~1.08(m,10H,2′-,3′-H and 3×CH 2 ); MS(m / z): Calcd.for C 21 h 22 FN 5 o 3 :411.44[M] + ;Found:412[M+H] + .

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Abstract

The invention discloses a 1-cyclopropyl-7-aminomethyl triazole-fluoroquinolones carboxylic acid derivative, a method for preparing the same and application of the 1-cyclopropyl-7-aminomethyl triazole-fluoroquinolones carboxylic acid derivative. The 1-cyclopropyl-7-aminomethyl triazole-fluoroquinolones carboxylic acid derivative is shown as a chemical structural general formula I, and R in the formula I can represent dimethylamino or lignocaine or piperidinyl or morpholino or piperazinyl or substituted piperazinyl or pyrrolidyl. The 1-cyclopropyl-7-aminomethyl triazole-fluoroquinolones carboxylic acid derivative, the method and the application have the advantages that framework-cyclopropyl fluoroquinolones carboxylic acid which is dominant pharmacophore, 7-amine which is an effective substituent and functional triazole heterocycle are effectively combined with one another, accordingly, the anti-drug-resistance activity of the 1-cyclopropyl-7-aminomethyl triazole-fluoroquinolones carboxylic acid derivative which is a novel chemical compound can be improved, and the 1-cyclopropyl-7-aminomethyl triazole-fluoroquinolones carboxylic acid derivative can be used as novel anti-infection medicine with novel antibacterial active substance development structures.

Description

technical field [0001] The invention belongs to the field of innovative drug synthesis, in particular to a 1-cyclopropyl-7-aminomethyltriazole-fluoroquinolone carboxylic acid derivative, and also to 1-cyclopropyl-7-aminomethyltriazole -The preparation method of fluoroquinolone carboxylic acid derivatives, and their application in anti-infection drugs. Background technique [0002] Fluoroquinolones have attracted much attention as broad-spectrum, high-efficiency, and low-toxic anti-infective drugs widely used in clinical practice. However, due to the increasing severity of bacterial drug resistance, how to overcome bacterial drug resistance has become an urgent social and public health security issue in the field of anti-infective drug therapy. Although there are many options for solving bacterial drug resistance strategies, an effective and economical approach is to optimize the structure based on the structural characteristics of existing drugs and continuously promote the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D401/14A61P31/04
CPCC07D401/04C07D401/14Y02A50/30
Inventor 胡国强胡海廷杨彤闫强吴书敏倪礼礼
Owner HENAN UNIVERSITY
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