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Antibacterial chloroxoquinoline derivative
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A technology of oxoquinoline and quinoline, applied in the field of chloroquine derivatives, can solve problems such as difficult to effectively eradicate Helicobacter pylori infection, failure of Helicobacter pylori eradication treatment, etc.
Active Publication Date: 2015-11-11
王子厚
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Embodiment 1
[0205] Example 1: Preparation of 7-fluoro-1-methyl-4-oxo-quinoline (compound 7a)
[0206] Starting from 7-fluoro-4(1H)-oxoquinoline 6a (5.0 mmol) and iodomethane (7.5 mmol). A white solid (0.86 g, 86%) was obtained. ESI-MSm / z178[M+H] + . 1 HNMR (300MHz, CDCl 3 ):δ8.40-8.45(1H,m),7.47(1H,d,J=7.5Hz),7.00-7.11(2H,m),6.20(1H,d,J=7.5Hz),3.74(3H, s).
Embodiment 2
[0207] Embodiment 2: Preparation of 7-chloro-1-methyl-4-oxo-quinoline (compound 7b)
[0209] Example 3: Preparation of 7-bromo-1-methyl-4-oxo-quinoline (compound 7c)
[0210] Starting from 7-bromo-4(1H)-oxoquinoline 6c (5.0 mmol) and iodomethane (7.5 mmol). A white solid (1.0 g, 88%) was obtained. ESI-MSm / z239[M+H] + . 1 HNMR (300MHz, CDCl 3 ):δ8.27(1H,d,J=8.7Hz),7.44-7.54(3H,m),6.23(1H,d,J=7.8Hz),3.76(3H,s). 13 CNMR (75MHz, CDCl 3 )δ176.5, 146.1, 128.5, 128.4, 127.1, 126.6, 126.0, 120.0, 109.9, 40.8.
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Abstract
The invention relates to an oxo-quinoline derivative with activity of resisting bacterial infection relevant diseases such as helicobacter pylori (Hp) infection disease. The invention specifically relates to a compound as shown in formula I in the specification, and a pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R<1> is selected from hydrogen, -C<1-6> alkyl, -C<2-6> alkenyl, -C<2-6> alkynyl, or -C<1-6> alkyl-phenyl, and the alkyl, alkenyl, alkynyl and phenyl can be randomly substituted by halogen, nitro, cyan, hydroxyl, -C<1-6> alkoxy and phenyl; R<3> is selected from hydrogen, -CONHR<31> and -COOR<32>, R<31> and R<32> are independently selected from -C<1-6> alkyl and -C<1-6> alkyl amino, and the amino is randomly substituted by one to two -C<1-6> alkyls; R<7> is selected from halogen, -C<1-6> alkoxy, morpholinyl or piperazinyl.
Description
[0001] This application is a divisional application of Chinese Patent Application No. 2013106523200 submitted on December 5, 2013, the entire contents of which are incorporated herein by reference. technical field [0002] The invention relates to a class of chlorooxyquine derivatives with antibacterial activity, a preparation method of the chlorooxyquine derivatives, and their application in the preparation of antibacterial drugs. Background technique [0003] 7-chloro-4-oxo-quinoline, generally known as chlorooxyquine, molecular formula: C 9 h 6 ClNO, molecular weight: 179.6, melting point: 282-285°C, white or off-white powder, its chemical structure is as follows: [0004] [0005] This compound has tautomerism, and its tautomer is 7-chloro-4-hydroxyl-quinoline, and the relationship between the two changes is as follows: [0006] [0007] It is known that chlorooxyquine is a new national anti-cancerdrug independently developed by Tonghua Maoxiang Pharmaceutical C...
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