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

A technology of fluoronaphthyridinone carboxylic acid and aminomethyltriazole, which is used in the preparation of 1-cyclopropyl-7-aminomethyltriazole-fluoronaphthyridinone carboxylic acid derivatives, and used in anti-infective drugs. Application, the field of 1-cyclopropyl-7-aminomethyltriazole-fluoronaphthyridone carboxylic acid derivatives to achieve the effect of overcoming drug resistance

Inactive Publication Date: 2015-08-05
HENAN UNIVERSITY
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  • Summary
  • 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 connecting chains between the piperazine group and the quinoline ring skeleton.

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] 1-cyclopropyl-6-fluoro-7-(4-dimethylaminomethyl-[1,2,3]triazol-1-yl)-[1,8]naphthyridin-4(1H)-one -3-carboxylic acid (I-1), its chemical structural formula is:

[0051]

[0052] That is, R in formula I is dimethylamino.

[0053] 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 82.0%, m.p.231-233°C . 1 H NMR (400MHz, DMSO-d 6 ): δ15.46(brs,1H,COOH),8.89(s,1H,2-H),8.17(d,J=13.2Hz,1H,5-H),7.88(s,1H,5″-H ),5.23(s,2H,NCH 2 ),3.67-3.56(m,1H,1′-H),2.44(s,6H,2×CH 3 ), 1.35~1.26 (m, 4H, 2′- and 3′-H); MS(m / z): Calcd.for C 17 h 17 FN 6 o 3 :372.36[M] + ;Found:373[M+H] + .

Embodiment 2

[0055] 1-cyclopropyl-6-fluoro-7-(4-diethylaminomethyl-[1,2,3]triazol-1-yl)-[1,8]naphthyridin-4(1H)-one -3-carboxylic acid (I-2), its chemical structural formula is:

[0056]

[0057] That is, R in formula I is diethylamino.

[0058] The preparation method of the compound is as follows: using diethylamine as the amine donor, according to the above-mentioned general preparation method of the target object (I), the light yellow crystal (I-2) is obtained, the yield is 71.0%, m.p.225-227°C . 1 H NMR (400MHz, DMSO-d 6 ):δ15.45(brs,1H,COOH),8.86(s,1H,2-H),8.16(d,J=13.2Hz,1H,5-H),7.86(s,1H,5″-H ),5.21(s,2H,NCH 2 ),3.71-3.64(m,1H,1′-H),2.46-2.38(m,4H,2×CH 2 ),1.32-1.15(m,10H,2′-,3′-H and 2×CH 3 ); MS(m / z): Calcd.for C 19 h 21 FN 6 o 3 :400.42[M] + ;Found:401[M+H] + .

Embodiment 3

[0060] 1-cyclopropyl-6-fluoro-7-(4-piperidine-1-methyl-[1,2,3]triazol-1-yl)-[1,8]naphthyridine-4(1H) - Keto-3-carboxylic acid (I-3), its chemical structural formula is:

[0061]

[0062] That is, R in formula I is piperidin-1-yl.

[0063] 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 76.0%, m.p.234-236°C. 1 H NMR (400MHz, DMSO-d 6 ):δ15.45(brs,1H,COOH),8.87(s,1H,2-H),8.14(d,J=13.2Hz,1H,5-H),7.88(s,1H,5″-H ),5.26(s,2H,NCH 2 ),3.67-3.64(m,1H,1′-H),3.06-2.27(m,4H,N(CH 2 ) 2 ), 1.63-1.04 (m, 10H, 2′-, 3′-H and 3×CH 2 ); MS(m / z): Calcd.for C 20 h 21 FN 6 o 3 :412.43[M] + ;Found:413[M+H] + .

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Abstract

The invention discloses a 1-cyclopropyl-7-aminomethyl triazole-fluoronaphthalene quinacridone carboxylic acid derivative, a method for preparing the same and application of the 1-cyclopropyl-7-aminomethyl triazole-fluoronaphthalene quinacridone carboxylic acid derivative. The 1-cyclopropyl-7-aminomethyl triazole-fluoronaphthalene quinacridone 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 pyrrolidyl or piperazinyl or substituted piperazinyl. The 1-cyclopropyl-7-aminomethyl triazole-fluoronaphthalene quinacridone carboxylic acid derivative, the method and the application have the advantages that functional triazole heterocycle can be inserted in a space between framework-cyclopropyl fluoronaphthalene quinacridone carboxylic acid which is dominant pharmacophore and 7-amine which is an effective substituent, accordingly, the anti-drug-resistance activity of the 1-cyclopropyl-7-aminomethyl triazole-fluoronaphthalene quinacridone carboxylic acid derivative which is a novel chemical compound can be improved, and the 1-cyclopropyl-7-aminomethyl triazole-fluoronaphthalene quinacridone 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, and specifically relates to a 1-cyclopropyl-7-aminomethyl triazole-flunalidinone carboxylic acid derivative, and also relates to 1-cyclopropyl-7-aminomethyl A preparation method of triazole-flunalidinone carboxylic acid derivatives and an application thereof in anti-infective 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 contin...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61P31/04
CPCC07D471/04
Inventor 闫强吴书敏王蕊倪礼礼杨彤胡国强
Owner HENAN UNIVERSITY