CN107098914A - A kind of chromene simultaneously [3 ', 4 ':5,6] pyrans simultaneously [2,3 b] quinoline and its preparation method and application - Google Patents
A kind of chromene simultaneously [3 ', 4 ':5,6] pyrans simultaneously [2,3 b] quinoline and its preparation method and application Download PDFInfo
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- CN107098914A CN107098914A CN201710352512.8A CN201710352512A CN107098914A CN 107098914 A CN107098914 A CN 107098914A CN 201710352512 A CN201710352512 A CN 201710352512A CN 107098914 A CN107098914 A CN 107098914A
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- quinoline
- chromene
- formaldehyde
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/153—Ortho-condensed systems the condensed system containing two rings with oxygen as ring hetero atom and one ring with nitrogen as ring hetero atom
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Abstract
A kind of chromene simultaneously [3 ', 4 ':5,6] pyrans simultaneously [2,3 b] quinoline, structure shown in its structural formula as I：Wherein, R1For H, CH3O, Cl or (CH3)3Any one in C；R2For H or CH3；R3For H, CH3Or Ph.The derivative is using formaldehyde of 2 chloroquinoline 3 or derivatives thereof, malononitrile and 4 Hydroxycoumarins as raw material, one-step synthesis.Raw material is simple, be easy to get, mild condition, and total recovery is up to 75%.The compound that the present invention is provided confirms that there is preferably external Inhibit proliferaton to act on to human body hepatoma cell line HepG2 through pharmacological evaluation, with the effect for suppressing growth of tumour cell, can be applied in antineoplastic is prepared.
Description
Technical field
The invention belongs to technical field of organic synthesis, it is related to chromene simultaneously [3 ', 4 ':5,6] simultaneously [2,3-b] quinoline spreads out pyrans
Biological preparation method, and the application in antineoplastic
Background technology
Chromene, also known as chromene, its skeleton are widely present in natural products, for example：Vitamin E, flavones, isoflavones
Deng all contain chromene skeleton.Chromene derivative has extensive biological and pharmacological activity.Existing antiallergy and anticancer isoreactivity side
The report in face.
Quinoline, is also benzo pyridine or azanaphthalene, is the very important nitrogen-containing heterocycle compound of a class, especially in pharmacy work
Had a wide range of applications in industry.Moreover, they are also the parent nucleus of many natural products and biologically active drug structure, such as：Chlorine
The peaceful alkali of quinoline, camel, camptothecine.By the continuous research of medicine scholar, substantial amounts of quinoline derivatives are synthesized, and it
Have extensive bioactivity, for example：Anti-malarial, antibacterial, anti-inflammatory, antitumor, anti-diabetic, anti-asthma, anti-hypertension,
Anti- alzheimer that disease, platelet aggregation-against, AntiHIV1 RT activity isoreactivity.
Pyranoquinoline is a kind of skeleton of alkaloid, and it is present in rutaceae, such compound due to
Extensive pharmacology and bioactivity and attract attention.There is pyranoquinoline class compound antibacterial, antiplatelet to gather
The bioactivity such as collection, anti-inflammatory, antiallergy, antihistamine.There is important bioactivity based on pyranoquinoline, this kind of compound
Synthesis technique causes the interest of people, and Liu in 2007 etc. reports the formamide of 1- acetyl group-N- aryl rings penta in sulfuric acid catalysis
Under cyclisation/open loop/cyclisation cascade reaction synthesized a series of pyrans simultaneously [2,3-b] quinoline.The report such as Singh in 2009
The coupling Cyclization method of 2- chloroquinoline -3- formaldehyde and alkynes under road palladium chtalyst.Verma in 2011 etc. reports catalysis of iodine
Coupling reaction under cyclisation and palladium chtalyst of the 2- alkynyl -3- quinoline aldehydes with alcohol has synthesized a series of pyrans simultaneously [4,3-b] quinoline
Quinoline derivant.But, these synthesis techniques use noble metal as catalyst the need for having, some synthesis materials are difficult to obtain.
How the raw material being easy to get using some, synthesize the novel pyranoquinoline derivatives of some structures by some simple methods and have
It is of great significance.
The content of the invention
Present invention solves the technical problem that being that the synthesis technique of pyranoquinoline in the prior art needs noble metal as urging
Agent, the defect that synthesis material is difficult to obtain there is provided a kind of chromene novel with a kind of structure of Material synthesis that is simple, being easy to get simultaneously
[3’,4’:5,6] pyrans simultaneously [2,3-b] quinoline.
A kind of chromene simultaneously [3 ', 4 ':5,6] pyrans simultaneously [2,3-b] quinoline, structure shown in its structural formula as I：
Wherein, R1For H, CH3O, Cl or (CH3)3Any one in C.
It is a kind of such as chromene simultaneously [3 ', 4 ':5,6] synthetic method of pyrans simultaneously [2,3-b] quinoline, with 2- chloroquinolines-
3- formaldehyde or derivatives thereof, malononitrile and 4 hydroxy coumarin are raw material, the compound shown in one-step synthesis Formulas I, its reaction side
Formula is as follows：
Described 2- chloroquinoline -3- formaldehyde derivatives be the chloro- 6- methoxy quinolines -3- formaldehyde of 2-, 2,6- dichloroquinolines -
Any one in 3- formaldehyde and the chloro- 6- tert-butyl groups quinoline-3-formaldehydes of 2-.
The solvent of reaction is acetonitrile, tetrahydrofuran, toluene, ethylene glycol, N,N-dimethylformamide (DMF), water and ethanol
Any of, wherein preferred alcohol.The catalyst of reaction can be alkali, for example sodium hydroxide, sodium carbonate, cesium carbonate, hexahydro
Pyridine or acid, such as p-methyl benzenesulfonic acid, acetic acid either organic micromolecule catalyst such as L-PROLINE.Preferably L-
Proline.
The mol ratio of 2- chloroquinoline -3- formaldehyde or derivatives thereof, malononitrile, 4 hydroxy coumarin and catalyst is 1:1:1:
0.1~0.6, preferably 1:1:1:0.5.
The temperature of reaction is 80~110 DEG C, and the reaction time is 20~50min；It is preferred that 100 DEG C, react 30min.
It is preferred that, 2- chloroquinoline -3- formaldehyde, malononitrile and 4 hydroxy coumarin, using L-PROLINE as catalyst, 100 DEG C
Reaction 20 minutes, the mol ratio of raw material is 3- chloroquinoline -3- formaldehyde：Malononitrile：4 hydroxy coumarin：L-PROLINE=1:1:1:
0.5, high income is up to 75%.
Beneficial effect：
The present invention utilizes multi-component reaction, and three kinds of raw materials that are simple, being easy to get are closed by the multi-component reaction of " treating different things alike "
Into chromene simultaneously [3 ', 4 ':5,6] pyrans simultaneously [2,3-b] quinoline, total recovery is up to 75%；The compound is a kind of suitable
Stable compound, there is preferably external Inhibit proliferaton to act on to human body hepatoma cell line HepG2, by extracorporeal anti-tumor
Active testing shows that most compounds have obvious antitumor activity, can be applied in antineoplastic.Wherein chemical combination
Thing 2- (6- oxo -6,7- dihydros chromenes simultaneously [3 ', 4 ':5,6] pyrans simultaneously [2,3-b] quinoline -7- bases) malononitrile (Ia), 2-
(10- methoxyl group -6- oxo -6,7- dihydros chromene simultaneously [3 ', 4 ':5,6] pyrans simultaneously [2,3-b] quinoline -7- bases) malononitrile
(Ib), 2- (the 10- tert-butyl group -6- oxo -6,7- dihydros chromenes simultaneously [3 ', 4 ':5,6] pyrans simultaneously [2,3-b] quinoline -7- bases) third
Dintrile (Ic), 2- (the chloro- 6- oxos -6,7- dihydros chromenes of 10- simultaneously [3 ', 4 ':5,6] pyrans simultaneously [2,3-b] quinoline -7- bases)
Malononitrile (Id) has good antitumor activity, their IC50Value is as follows：
Embodiment
Embodiment 1
2- chloroquinoline -3- formaldehyde (0.2mmol), malononitrile (0.2mmol) and 4 hydroxy coumarin (0.2mmol) are added
Into 5mL microwave reaction pipes, L-PROLINE (0.1 mmol) and ethanol 2mL are added, the seal of tube will be reacted, 10 are stirred in advance
Second, mixture reacts 30 minutes under microwave radiation in 100 DEG C, after reaction terminates, reaction system is cooled into room temperature, waits to separate out
Suction filtration is carried out after solid, then carries out with the mixed solvent of DMF and water being recrystallized to give 2- that (6- oxo -6,7- dihydros chromene is simultaneously
[3’,4’:5,6] pyrans simultaneously [2,3-b] quinoline -7- bases) malononitrile (Ia)：Yield 71%；m.p.:274-276℃；IR(KBr,
ν,cm-1):2917,2250,1701, 1638,1607,1493,1404,1332,1244,1204,1169,1151,1050,
1025,987, 769,754；1H NMR(400MHz,DMSO-d6)(δ,ppm):8.84 (s, 1H, ArH), 8.15 (d, J=
8.0Hz, 2H, ArH), 8.04 (d, J=8.4Hz, 1H, ArH), 7.94-7.90 (m, 1H, ArH), 7.86-7.82 (m, 1H,
ArH), 7.70 (t, J=7.6Hz, 1H, ArH), 7.61 (d, J=8.4 Hz, 1H, ArH), 7.57 (t, J=8.0Hz, 1H,
), ArH 5.38 (d, J=4.0Hz, 1H, CH), 5.34 (d, J=3.6Hz, 1H, CH)13C NMR(100MHz,DMSO-d6)(δ,
ppm):162.3, 160.0,158.5,153.7,152.6,145.6,140.8,134.0,131.9,128.3,127.6,
127.0,126.9,125.2,123.0,117.0,113.2,113.1,112.7,112.4,98.4,35.7, 35.2,30.7,
30.4.HRMS Calcd for C22H12N3O3[(M+H)+]366.0879；Found 366.0870.
Embodiment 2
According to the method for embodiment 1,2- chloroquinoline -3- formaldehyde is changed into 6- methoxyl group -2- chloroquinoline -3- formaldehyde, with L-
Proline is catalyst, is reacted 30 minutes under microwave radiation, after reaction terminates, reaction system is cooled into room temperature, waits to separate out
Suction filtration is carried out after solid, target product 2- (10- methoxyl group -6- oxos -6,7- are recrystallized to give with DMF and water mixed solvent
Dihydro chromene simultaneously [3 ', 4 ':5,6] pyrans simultaneously [2,3-b] quinoline -7- bases) malononitrile (Ib)：Yield 75%；m.p.: 258-
260℃；IR(KBr,ν,cm-1):2903,2254,1686,1637,1609,1497,1455, 1353,1236,1172,1113,
1025,1005,993,794,747；1H NMR(400MHz, DMSO-d6)(δ,ppm):8.69(s,1H,ArH),8.14-8.11
(m, 1H, ArH), 7.94 (d, J=9.2Hz, 1H, ArH), 7.85-7.81 (m, 1H, ArH), 7.61-7.53 (m, 4H, ArH),
5.35 (d, J=3.6Hz, 1H, CH), 5.31 (d, J=3.6Hz, 1H, CH), 3.94 (s, 3H, CH3O).13C NMR (75MHz,
DMSO-d6)(δ,ppm):160.5,159.0,158.1,153.1,152.6,141.7, 139.6,134.4,129.5,128.6,
125.7,124.9,123.4,117.4,113.7,113.6, 113.2,112.9,106.4,98.7,56.2,35.7,
30.8.HRMS Calcd for C23H14N3O4 [(M+H)+]396.0984；Found 396.0981.
Embodiment 3
According to the method for embodiment 1,2- chloroquinoline -3- formaldehyde is changed into the 6- tert-butyl group -2- chloroquinoline -3- formaldehyde, with L-
Proline is catalyst, is reacted 30 minutes under microwave radiation, after reaction terminates, reaction system is cooled into room temperature, waits to separate out
Suction filtration is carried out after solid, target product 2- (the 10- tert-butyl group -6- oxos -6,7- are recrystallized to give with DMF and water mixed solvent
Dihydro chromene simultaneously [3 ', 4 ':5,6] pyrans simultaneously [2,3-b] quinoline -7- bases) malononitrile (Ic)：Yield 73%；m.p.: 284-
286℃；IR(KBr,ν,cm-1):2963,2255,1702,1640,1610,1497,1460, 1438,1396,1380,1366,
1271,1183,1169,1150,1126,1098,988,969, 915,831；1H NMR(400MHz,DMSO-d6)(δ,ppm):
8.82 (s, 1H, ArH), 8.17 (d, J=7.6Hz, 1H, ArH), 8.09-8.00 (m, 3H, ArH), 7.86 (t, J=8.0Hz,
1H, ArH), 7.64-7.58 (m, 2H, ArH), 5.38 (d, J=3.6Hz, 1H, CH), 5.34 (d, J=3.6 Hz, 1H, CH),
1.45(s,9H,(CH3)3C).13C NMR(75MHz,DMSO-d6)(δ,ppm): 160.5,158.9,153.9,153.1,
150.0,144.5,141.1,134.5,131.4,127.7, 127.1,125.7,123.4,117.4,113.7,113.2,
112.9,98.8,35.8,35.3,31.3, 31.9.HRMS Calcd for C26H20N3O3[(M+H)+]422.1510；Found
422.1505.
Embodiment 4
According to the method for embodiment 1,2- chloroquinoline -3- formaldehyde is changed into 2,6- dichloroquinoline -3- formaldehyde, with L- dried meat ammonia
Acid is catalyst, is reacted 30 minutes under microwave radiation, and after reaction terminates, reaction system is cooled into room temperature, solid to be separated out
After carry out suction filtration, target product 2- (chloro- 6- oxos -6, the 7- dihydro colors of 10- are recrystallized to give with DMF and water mixed solvent
Alkene simultaneously [3 ', 4 ':5,6] pyrans simultaneously [2,3-b] quinoline -7- bases) malononitrile (Id)：Yield 69%；m.p.: 284-286℃；IR
(KBr,ν,cm-1):2903,2256,1689,1642,1604,1577,1417, 1392,1344,1272,1206,1119,
1050,1024,991,930,823,767；1H NMR (400MHz,DMSO-d6)(δ,ppm):8.82(s,1H,ArH),8.32
(d, J=2.4Hz, 1H, ArH), 8.14-8.11 (m, 1H, ArH), 8.05 (d, J=9.2Hz, 1H, ArH), 7.92-7.90 (m,
1H, ArH), 7.86-7.82 (m, 1H, ArH), 7.61 (d, J=8.4Hz, 1H, ArH), 7.59-7.55 (m, 1H, ArH), 5.38
(d, J=3.6Hz, 1H, CH), 5.34 (d, J=3.6Hz, 1H, CH)13C NMR(100MHz,DMSO-d6)(δ,ppm):
162.3,159.9,158.3,154.0,152.6, 144.1,140.1,134.0,132.4,131.4,129.7,127.6,
126.9,125.2,122.9, 116.9,114.4,113.1,112.6,112.4,98.4,35.2,30.3.HRMS Calcd
for C22H9ClN3O3[(M-H)-]398.0332；Found 398.0330.
The general principle and principal character and advantages of the present invention of the present invention has been shown and described above.The skill of the industry
Art personnel are it should be appreciated that the present invention is not limited to the above embodiments, and described in above-described embodiment and specification is explanation
The principle of the present invention, without departing from the spirit and scope of the present invention, various changes and modifications of the present invention are possible, these
Changes and improvements all fall within the protetion scope of the claimed invention.The claimed scope of the invention by appended claims and
Its equivalent thereof.
Claims (9)
1. a kind of chromene simultaneously [3 ', 4 ':5,6] pyrans simultaneously [2,3-b] quinoline, structure shown in its structural formula as I：
Wherein, R1For H, CH3O, Cl or (CH3)3Any one in C.
2. a kind of chromene as claimed in claim 1 simultaneously [3 ', 4 ':5,6] the synthesis side of pyrans simultaneously [2,3-b] quinoline
Method, it is characterised in that using 2- chloroquinoline -3- formaldehyde or derivatives thereof, malononitrile and 4 hydroxy coumarin as raw material, one-step synthesis
Compound shown in Formulas I, its reaction equation is as follows：
3. chromene as claimed in claim 2 simultaneously [3 ', 4 ':5,6] synthetic method of pyrans simultaneously [2,3-b] quinoline, its
It is characterised by, described 2- chloroquinoline -3- formaldehyde derivatives are the chloro- 6- methoxy quinolines -3- formaldehyde of 2-, 2,6- dichloroquinolines -
Any one in 3- formaldehyde and the chloro- 6- tert-butyl groups quinoline-3-formaldehydes of 2-.
4. chromene as claimed in claim 2 simultaneously [3 ', 4 ':5,6] synthetic method of pyrans simultaneously [2,3-b] quinoline, its
It is characterised by, the solvent of reaction is in acetonitrile, tetrahydrofuran, toluene, ethylene glycol, DMF, water and ethanol
It is any.
5. chromene as claimed in claim 2 simultaneously [3 ', 4 ':5,6] synthetic method of pyrans simultaneously [2,3-b] quinoline, its
It is characterised by, the catalyst of reaction is sodium hydroxide, sodium carbonate, cesium carbonate, hexahydropyridine, p-methyl benzenesulfonic acid, acetic acid and L- dried meat
Any one or a few in propylhomoserin.
6. chromene as claimed in claim 5 simultaneously [3 ', 4 ':5,6] synthetic method of pyrans simultaneously [2,3-b] quinoline, its
It is characterised by, the mol ratio of 2- chloroquinoline -3- formaldehyde or derivatives thereof, malononitrile, 4 hydroxy coumarin and catalyst is 1:1:
1:0.1~0.6.
7. chromene as claimed in claim 2 simultaneously [3 ', 4 ':5,6] synthetic method of pyrans simultaneously [2,3-b] quinoline, its
It is characterised by, the temperature of reaction is 80~110 DEG C, and the reaction time is 20~50min.
8. chromene as claimed in claim 2 simultaneously [3 ', 4 ':5,6] synthetic method of pyrans simultaneously [2,3-b] quinoline, its
It is characterised by, 2- chloroquinoline -3- formaldehyde, malononitrile and 4 hydroxy coumarin, using L-PROLINE as catalyst, 100 DEG C of reactions 30
Minute, the mol ratio of raw material is 2- chloroquinoline -3- formaldehyde：Malononitrile：4 hydroxy coumarin：L-PROLINE=1:1:1:0.5.
9. a kind of chromene as claimed in claim 1 simultaneously [3 ', 4 ':5,6] simultaneously [2,3-b] quinoline is preparing anti-swell to pyrans
Application in tumor medicine.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113234083A (en) * | 2021-04-16 | 2021-08-10 | 华南理工大学 | Tetrahydroquinoline pyran compound and preparation method and application thereof |
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| CN102584841A (en) * | 2011-12-16 | 2012-07-18 | 浙江工业大学 | Quinoline coumarin derivate and preparation method and application thereof |
| CN102757446A (en) * | 2012-07-30 | 2012-10-31 | 李佰林 | Synthesis method of pyranocoumarin derivatives |
| CN106632364A (en) * | 2016-12-22 | 2017-05-10 | 精华制药集团南通有限公司 | Pyrano[2,3-b]quinoline derivative as well as synthesis method and anti-tumor application thereof |
| CN108218883A (en) * | 2016-12-22 | 2018-06-29 | 精华制药集团南通有限公司 | A kind of simultaneously [2,3-b] quinoline and its synthesis technology and the application in anti-tumor aspect of pyrans |
-
2017
- 2017-05-18 CN CN201710352512.8A patent/CN107098914A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102584841A (en) * | 2011-12-16 | 2012-07-18 | 浙江工业大学 | Quinoline coumarin derivate and preparation method and application thereof |
| CN102757446A (en) * | 2012-07-30 | 2012-10-31 | 李佰林 | Synthesis method of pyranocoumarin derivatives |
| CN106632364A (en) * | 2016-12-22 | 2017-05-10 | 精华制药集团南通有限公司 | Pyrano[2,3-b]quinoline derivative as well as synthesis method and anti-tumor application thereof |
| CN108218883A (en) * | 2016-12-22 | 2018-06-29 | 精华制药集团南通有限公司 | A kind of simultaneously [2,3-b] quinoline and its synthesis technology and the application in anti-tumor aspect of pyrans |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113234083A (en) * | 2021-04-16 | 2021-08-10 | 华南理工大学 | Tetrahydroquinoline pyran compound and preparation method and application thereof |
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