CN102532016A - 5-aminoquinoline-2(1H) ketone compound and synthetic method and application thereof - Google Patents

5-aminoquinoline-2(1H) ketone compound and synthetic method and application thereof Download PDF

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CN102532016A
CN102532016A CN2011103637268A CN201110363726A CN102532016A CN 102532016 A CN102532016 A CN 102532016A CN 2011103637268 A CN2011103637268 A CN 2011103637268A CN 201110363726 A CN201110363726 A CN 201110363726A CN 102532016 A CN102532016 A CN 102532016A
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quinolylamine
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吉庆刚
刘洪彬
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Southwest University
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Abstract

The invention discloses a novel 5-aminoquinoline-2(1H) ketone compound and a synthetic method and application thereof. A structure of the kind of compound is shown as the general formula I, (molecular formula) I, AR of (molecular formula) or (molecular formula). R1, R2 and R3 are hydrogen, halogen, methoxy group, methyl, nitro or acetoxyl group, R4 is hydrogen or acetyl, and X is oxygen or sulfur. A bioactivity test demonstrates that the 5-aminoquinoline-2(1H) ketone compound serves as an antimicrobial agent, is good in antimicrobial agent, and can be used for preparing drugs of etiology-resistant microorganism.

Description

5-quinolylamine-2 (1H) ketone compounds and preparation method and use thereof
Technical field
The present invention relates to the novel quinoline ketone compounds, be specifically related to a kind of 5-quinolylamine-2 (1H) ketone compounds and compound method and application.
Background technology
The quinolinones medicine is one type of antibacterials of synthetic, and its activity at aspects such as antibiotic, antimycotic, antitumor, antiviral, anxiety, xitix has caused that people note widely.Since the fixed acid of first quinolinones medicine naphthalene in 1962 occurs so far, people developed in succession four generation the quinolinones medicine, be widely used in veterinary clinic, chemoprophylaxis and treatment various bacteria and mycoplasma disease at present.But life-time service along with the quinolinones medicine; Therefore its resistance continues the continuous transformation to its structure, in recent years also in quick growth; 2-(1H) quinolinones compound all has report in the application of aspects such as sensitive materials, antiviral, antitumour activity, chitinase inhibitors; The research article of this compounds is visible: Bioconjugate Chem.2004,75,1088-1094; J.Med.Chem.2006,49,971-983; J.Med.Chem.2010,53,7739-7755; Organic Process Research&Development 2004,8,643-650; Bioorg.Med.Chem.Lett.10 (2000) 1459-1462.These documents all do not cover or comprise structure, the preparation method and use of novel cpd involved in the present invention.
At present, continue searching and have stronger activity and bioactive quinolinones medicine, making bigger contribution for human beings'health is current pressing for, and is the focus of various countries scientist research.
Summary of the invention
The object of the present invention is to provide 5-quinolylamine-2 (1H) ketone compounds.
Another object of the present invention is to provide the compound method of above-claimed cpd.
A purpose more of the present invention is to provide the purposes of above-claimed cpd.
The objective of the invention is to realize through following technical scheme:
5-quinolylamine-2 (1H) ketone compounds, it is characterized in that: the structure of said compound is shown in general formula I:
Figure BDA0000108849370000011
Wherein Ar is:
Figure BDA0000108849370000021
Perhaps
Figure BDA0000108849370000022
R 1, R 2, R 3Be hydrogen, halogen, methoxyl group, methyl, nitro or acetoxyl group; R 4Be hydrogen or ethanoyl; X is O or S.
Used in the present invention term " halogen " has the common implication in present technique field, promptly comprises fluorine, chlorine, bromine and iodine.
For example, specifically, R 1Be hydrogen, halogen, acetoxyl group, methyl or methoxy; R 2Be hydrogen, halogen, nitro, methyl or methoxy; R 4Be hydrogen or ethanoyl; X is O or S; More particularly, above-mentioned 5-quinolylamine-2 (1H) ketone compounds specifically can be:
Wherein Ar is 4-CH 3OC 6H 4, 4-ClC 6H 4, 2,4-ClC 6H 4, 4-O 2NC 6H 4, 4-CH 3C 6H 4, 4-FC 6H 4, 2-ClC 6H 4, C 4H 3O, 2-C 5H 4N, 5-CH 3COC 4H 2S, 2-C 4H 3S, 2-CH 3COOC 6H 4, 2-CH 3OC 6H 4, 2-CH 3C 6H 4Or 3-FC 6H 4Or the like.Above-mentioned substance is the particular compound of the unique corresponding structural formula of difference, and this is well known to a person skilled in the art.
The compound method of above-mentioned 5-quinolylamine-2 (1H) ketone compounds is performed as follows:
Shown in Scheme1,
Figure BDA0000108849370000024
A) by hydroresorcinol and ammonium acetate reaction, obtain 3,4,7 with the vinylformic acid reflux then, 8-tetrahydroquinoline-2,5-(1H, 6H)-diketone, reflux with oxammonium hydrochloride again and make oxime;
B) oxime in DMF with Benzoyl chloride 99min. reaction, then behind the semmeler-wollf aromatization again the aqueous hydrochloric acid hydrolysis make 5-amino-3,4-EEDQ-2 (1H)-ketone;
C) 5-amino-3, and 4-EEDQ-2 (1H)-ketone and corresponding fragrant formyl isocyanate reaction obtain the compound that general formula is I.
Specifically, above-mentioned Scheme1 reaction conditions 1) mol ratio of hydroresorcinol and ammonium acetate is 1: 1.5,100 ℃ of temperature of reaction; 2) 3-amino-hexamethylene-2-ketenes and vinylformic acid mol ratio are 1: 1.5,120 ℃ of reactions of temperature of reaction; 3) tetrahydroquinoline-2,5 (1H, 6H) diketone and oxammonium hydrochloride, salt of wormwood mol ratio are 1: 1.2: 0.6, solvent is a water, is heated to 80 ℃; 4) 5-oximido-six hydrogen quinoline-2 (1H) ketone and Benzoyl chloride 99min., sodium hydride mol ratio are 1: 1.01: 1.01,0～5 ℃ of temperature of reaction, and solvent is DMF; 5) 5-benzoyl oxygen oximido-six hydrogen quinoline-2 (1H) ketone and acetic anhydride mol ratio are 1: 12,100～110 ℃ of temperature of reaction; 6) N-(2-carbonyl-tetrahydroquinoline-5-yl) ethanamide 100 ℃ of reactions in dilute hydrochloric acid solution; 7) 5-amino-quinoline 2 (1H) ketone and fragrant formyl isocyanic ester mol ratio are 1: 1, and temperature of reaction makes 5-quinolylamine-2 (1H) ketone compounds for 25～50 ℃.
The synthetic route of above-mentioned fragrant formyl isocyanic ester 8 is shown in Scheme2:
Figure BDA0000108849370000031
Scheme2 reaction conditions 1) aromatic acid and thionyl chloride, ammoniacal liquor mol ratio are 1: 1.5: 3,65～70 ℃ of temperature of reaction, 5h; Splash into ammoniacal liquor under the ice bath again.2) the fragrant methane amide of gained and oxalyl chloride mol ratio are 1: 2, rise to 50 ℃ of reaction 5h behind the 25 ℃ of reactions 2h of elder generation and are warmed up to 85 ℃ of reaction 5h again.
Those of ordinary skills all can make corresponding compounds by above-mentioned disclosed preparation method.
The application of above-mentioned 5-quinolylamine-2 (1H) ketone compounds in preparation resisting pathogenic microbes medicine.Said mikrobe is pathogenetic bacteria or pathogenic fungi, like intestinal bacteria, streptococcus aureus, Bacillus subtilus, Bacillus proteus, Candida albicans bacterium etc.
Pharmaceutical composition, 5-quinolylamine-2 (1H) ketone compounds and pharmaceutically acceptable carrier that it is above-mentioned.
Embodiment
In order to make the object of the invention, technical scheme clearer, below the preferred embodiments of the present invention are described in detail.Be noted that: above embodiment only is used for the present invention is further specified; Can not be interpreted as the restriction to protection domain of the present invention, some nonessential improvement that those skilled in the art's foregoing according to the present invention is made and adjustment all belong to protection scope of the present invention.
Embodiment 1: the preparation of compound 3-amino-hexamethylene-2-ketenes
Figure BDA0000108849370000032
In having the 100ml flask of calcium chloride tube, add hydroresorcinol 3.36g, ammonium acetate 3.23g; Be heated with stirring to 100 ℃ of reaction 30min, stopped reaction is cooled to room temperature, adds the 10ml re-crystallizing in ethyl acetate; Suction filtration, dry yellow crystals 3.19g, the yield 98.7% of getting.
Embodiment 2: compound tetrahydroquinoline-2,5 (1H, 6H) preparation of diketone
Figure BDA0000108849370000041
2.22g compound 2 and 2.16g vinylformic acid are added in the 50ml flask, be heated with stirring to 120 ℃ of reaction 4h, stopped reaction is cooled to room temperature, adds 5ml absolute ethyl alcohol recrystallization, suction filtration, the dry yellow crystals 2.05g that gets.Yield 62.2%.
Embodiment 3: the preparation of compound 5-oximido-six hydrogen quinoline-2 (1H) ketone
Figure BDA0000108849370000042
In the 50ml three-necked flask, add 20ml water, 0.636g yellow soda ash is after the stirring and dissolving; Slowly add oxammonium hydrochloride 0.834g, produce the back until no bubble and add 1.65g compound 2, Glacial acetic acid min. 99.5 is regulated PH about 5; Be warming up to 84 ℃ of reaction 5.5h, stopped reaction is cooled to room temperature; Suction filtration, dry 1.318g white solid, the yield 73.2% of getting.
Embodiment 4: the preparation of compound 5-benzoyl oxygen oximido-six hydrogen quinoline-2 (1H) ketone
Figure BDA0000108849370000043
In the 50ml three-necked flask, add dry 20ml dry DMF, 1.8g compound 3 and 0.264g sodium hydride, drip the DMF solution of 1.55g Benzoyl chloride 99min. under the ice bath cooling behind the stirring 10min, drip off back room temperature reaction 4h; Stopped reaction; Pour in the 100ml frozen water suction filtration, saturated sodium carbonate solution washing into; Dry 2.125g white solid, the yield 74.8% of getting.
Embodiment 5: the preparation of compound N-(2-carbonyl-tetrahydroquinoline-5-yl) ethanamide
Figure BDA0000108849370000051
Adding 15ml Glacial acetic acid min. 99.5,1.42g compound 4,5.1g acetic anhydride in the 50ml flask stir and are warming up to 110 ℃ of reaction 5h, stopped reaction, and solvent distillation adds ETHYLE ACETATE, suction filtration, ETHYLE ACETATE washing, the dry 0.56g pale yellow powder shape solid that gets.Bullion yield 55%.
Embodiment 6: the preparation of compound 5-amino-quinoline-2 (1H) ketone
Figure BDA0000108849370000052
Add 29ml water, 35ml concentrated hydrochloric acid in the 100ml flask, stir adding 4.7g bullion 5 down, be warming up to 100 ℃ of reaction 5h, stopped reaction, ice bath cooling crystallization; Suction filtration, dry 2.085g hydrochloride, with hydrochloride with the 50ml dissolve with methanol after, adding 1.765g sodium hydrogencarbonate; 65 ℃ of stirrings, activated carbon decolorizing, suction filtration, filtrating is revolved dried; The normal hexane washing, dry 1.6g yellow solid, yield 37.3%, the ESI-MS (m/z): 163 [M] of getting + 1HNMR (D 2O): 2.508 (t, 2H, J=7.2Hz); 2.837 (t, 2H, J=7.2Hz); 6.853 (d, 1H, J=7.8Hz); 6.970 (d, 1H, J=7.8Hz); 7.193 (t, 1H, J=7.8Hz).
Embodiment 7: compound is to the preparation of methoxybenzoyl isocyanic ester
Figure BDA0000108849370000053
Add the 35ml anhydrous chloroform in the 100ml flask, add 2.5g anisic acid, 3.88g thionyl chloride successively under stirring, be warming up to back flow reaction 4h, revolve dried solvent, add the 10ml dry THF, drip 2.23g ammoniacal liquor below 5 ℃.Separate out solid immediately, continue to stir 10min, add saturated sodium carbonate solution, suction filtration, the dry 2.207g white solid that gets is to methoxy benzamide.Yield 88.8%.
In the 50ml flask, add 0.4g to methoxy benzamide, 15ml1,2-ethylene dichloride; Ice bath drips 1 of oxalyl chloride down, and the 2-dichloroethane solution drips back room temperature reaction 2h; Be warming up to back flow reaction 5h behind 50 ℃ of reaction 5h; Stopped reaction revolves dried solvent, adds the anhydrous THF of 10ml and continues to revolve dried.Get the orange viscous liquid, subsequent use.
Embodiment 8: the preparation of compound 1-(to the methoxybenzoyl base)-3-(2-carbonyl-tetrahydroquinoline-5-yl) urea
Figure BDA0000108849370000061
In the 50ml flask, add the 10ml dry DMF, 0.4g compound 7, the compound 8a of dropping prepared fresh under the stirring at room; There is solid to separate out immediately, continues to be warming up to 45 ℃ of reaction 2h, stopped reaction behind the reaction 1h; Be cooled to room temperature, suction filtration, methanol wash; Dry 0.539g white solid, the yield 60% of getting.
With reference to above-mentioned instance, can synthesize following structural compounds
Figure BDA0000108849370000062
Ar＝9a 4-CH 3OC 6H 4 9b 4-ClC 6H 4 9c 2，4-ClC 6H 3 9d 4-O 2NC 6H 4 9e 4-CH 3C 6H 4
9f 4-FC 6H 4 9g 2-ClC 6H 4 9h C 4H 3O 9i C 5H 4N 9j 2-CH 3COC 4H 3S
9k C 4H 3S 9l 2-CH 3COOC 6H 4 9m 2-CH 3OC 6H 4 9n 2-CH 3C 6H 4 9o 3-FC 6H 4
With reference to above-mentioned instance 7 experimental procedures, can make corresponding fragrant formyl isocyanic ester 8b-8o; With reference to above-mentioned instance 8 experimental procedures, can make corresponding carbamide compounds 9b-9o from fragrant formyl isocyanic ester 8b-8o.
Embodiment 9: the above-mentioned compound that makes, measure fusing point (not proofreading and correct) through the accurate micro melting point apparatus of X-6; 1HNMR (300MHz) spectrum is measured with BrukerAv-300 type fourier transform NMR appearance, and ESI-MS (m/z) spectrum is measured with HTC liquid chromatography mass combined instrument, and its concrete analysis data are following:
Figure BDA0000108849370000063
Figure BDA0000108849370000081
Figure BDA0000108849370000091
Embodiment 10: the experiment of 5-quinolylamine-2 of the present invention (1H) ketone compounds antimicrobial acivity
Compound of the present invention is with after the DMSO dissolving, is mixed with solution with uncolled autoclaved solid medium also, and after pressing gradient dilution successively; Solution is poured in the flat board, after the cooling, added 20ul bacterium liquid; Evenly spread upon on the agar, contrast as reference with Streptomycin sulphate.Bacterium was cultivated 24 hours at 37 degree, and fungi is spent cultivation after 48 hours, observe phenomena 25.The result sees attached list.
Subordinate list, 5-quinolylamine-2 of the present invention (1H) ketone compounds antimicrobial acivity data (MIC ug/ml)
Figure BDA0000108849370000092
Figure BDA0000108849370000101
Above-mentioned experiment contrast Streptomyces antibiotic medicine be the very strong microbiotic of antimicrobial acivity of generally acknowledging, but it has occurred mikrobe resistance phenomenon at present.New compound of the present invention has no drug resistance; Above-mentioned activity data result shows, new compound of the present invention has significantly bacteriostatic action, and is wherein better to the restraining effect of the restraining effect comparison fungi of bacterium; Especially; Compound 9l all shows significant inhibitory effect to bacterium, and it can reach 25ug/ml to streptococcus aureus, Bacillus subtilus MIC, and is very approaching with the Streptomycin sulphate effect.

Claims (9)

1.5-quinolylamine-2 (1H) ketone compounds, it is characterized in that: the structure of said compound is shown in general formula I:
Figure FDA0000108849360000011
Wherein Ar is:
Figure FDA0000108849360000012
Perhaps
Figure FDA0000108849360000013
R 1, R 2, R 3Be hydrogen, halogen, methoxyl group, methyl, nitro or acetoxyl group; R 4Be hydrogen or ethanoyl; X is O or S.
2. 5-quinolylamine-2 (1H) ketone compounds according to claim 1 is characterized in that: said R 1Be hydrogen, halogen, acetoxyl group, methyl or methoxy; R 2Be hydrogen, halogen, nitro, methyl or methoxy.
3. 5-quinolylamine-2 (1H) ketone compounds according to claim 1, it is characterized in that: said 5-quinolylamine-2 (1H) ketone compounds can be:
Figure FDA0000108849360000014
Wherein Ar is 4-CH 3OC 6H 4, 4-ClC 6H 4, 2,4-ClC 6H 4, 4-O 2NC 6H 4, 4-CH 3C 6H 4, 4-FC 6H 4, 2-ClC 6H 4, C 4H 3O, 2-C 5H 4N, 5-CH 3COC 4H 2S, 2-C 4H 3S, 2-CH 3COOC 6H 4, 2-CH 3OC 6H 4, 2-CH 3C 6H 4Or 3-FC 6H 4
4. like the compound method of claim 1,2 or 3 said 5-quinolylamine-2 (1H) ketone compounds, be performed as follows, shown in Scheme1:
Figure FDA0000108849360000021
A) by hydroresorcinol and ammonium acetate reaction, obtain 3,4,7 with the vinylformic acid reflux then, 8-tetrahydroquinoline-2,5-(1H, 6H)-diketone, reflux with oxammonium hydrochloride again and make oxime;
B) oxime in DMF with Benzoyl chloride 99min. reaction, then behind the semmeler-wollf aromatization again the aqueous hydrochloric acid hydrolysis make 5-amino-3,4-EEDQ-2 (1H)-ketone;
C) 5-amino-3, and 4-EEDQ-2 (1H)-ketone and corresponding fragrant formyl isocyanate reaction obtain the compound that general formula is I.
5. compound method as claimed in claim 4 is characterized in that: the mol ratio of hydroresorcinol and ammonium acetate is 1: 1.5 in the said Scheme1 reaction 1,100 ℃ of temperature of reaction; 3-amino-hexamethylene-2-ketenes and vinylformic acid mol ratio are 1: 1.5 in the reaction 2,120 ℃ of reactions of temperature of reaction; Tetrahydroquinoline-2,5 in the reaction 3 (1H, 6H) diketone and oxammonium hydrochloride, salt of wormwood mol ratio are 1: 1.2: 0.6, and solvent is a water, is heated to 80 ℃; 5-oximido-six hydrogen quinoline-2 (1H) ketone and Benzoyl chloride 99min., sodium hydride mol ratio are 1: 1.01: 1.01 in the reaction 4,0～5 ℃ of temperature of reaction, and solvent is DMF; 5-benzoyl oxygen oximido-six hydrogen quinoline-2 (1H) ketone and acetic anhydride mol ratio are 1: 12 in the reaction 5,100～110 ℃ of temperature of reaction; N-(2-carbonyl-tetrahydroquinoline-5-yl) ethanamide temperature of reaction in dilute hydrochloric acid solution is 100 ℃ in the reaction 6; 5-amino-quinoline 2 (1H) ketone and fragrant formyl isocyanic ester mol ratio are 1: 1 in the reaction 7, and temperature of reaction makes 5-quinolylamine-2 (1H) ketone compounds for 25～50 ℃.
6. like claim 4 or 5 described compound methods, it is characterized in that: the synthetic route of said fragrant formyl isocyanic ester is shown in Scheme2:
Figure FDA0000108849360000022
Aromatic acid and thionyl chloride, ammoniacal liquor mol ratio are 1: 1.5: 3 in the reaction conditions 1,65～70 ℃ of temperature of reaction, 5h; Splash into ammoniacal liquor under the ice bath again; In the reaction 2 with the fragrant methane amide of gained and oxalyl chloride with mol ratio 1: 2, rise to 50 ℃ of reaction 5h earlier behind 25 ℃ of reaction 2h and be warmed up to 85 ℃ again and react 5h.
7. like claim 1, the application of 2 or 3 said 5-quinolylamine-2 (1H) ketone compounds in preparation resisting pathogenic microbes medicine.
8. like the application of the said 5-quinolylamine-2 of claim 7 (1H) ketone compounds in preparation resisting pathogenic microbes medicine, it is characterized in that: said mikrobe is pathogenetic bacteria or pathogenic fungi.
9. pharmaceutical composition, it is characterized in that: it contains claim 1,2 or 3 described 5-quinolylamine-2 (1H) ketone compounds and pharmaceutically acceptable carriers.
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CN112390725A (en) * 2019-08-16 2021-02-23 沈阳中化农药化工研发有限公司 Preparation method of amide compound

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CN110713459A (en) * 2019-12-04 2020-01-21 西南大学 Design synthesis and application of quinolinone fumaramide derivatives

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