CN105384702B - Three substitution s-triazine compounds and preparation method thereof - Google Patents

Three substitution s-triazine compounds and preparation method thereof Download PDF

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CN105384702B
CN105384702B CN201510920677.1A CN201510920677A CN105384702B CN 105384702 B CN105384702 B CN 105384702B CN 201510920677 A CN201510920677 A CN 201510920677A CN 105384702 B CN105384702 B CN 105384702B
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compound
formula
preparation method
shown
hydrogen
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CN201510920677.1A
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CN105384702A (en
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张辰
郭顺娜
张立宇
李晓
崔冬梅
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浙江大学
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D251/00Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/16Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C07D251/18Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines

Abstract

The present invention provides one kind three and substitutes s-triazine compound, by the hydrochloride of biguanide compound and 1, the mixing of 1 dibromoethylene class compound is added in organic solvent, under the catalysis of metallic copper, in the presence of part and alkali, stirring reaction 2~25 hours at a temperature of 60~130 DEG C, target compound is made through handling.The preparation method for developing three novel substitution s-triazine compounds of structure of the present invention, the technological reaction mild condition, easy to operate, cost is low, there is extensive prospects for commercial application.Three substitutions s-triazine compound provided by the present invention shows certain anti-breast cancer activity, is laid a good foundation for new medicament screen and exploitation, has preferable practical value.General structure is as follows.

Description

Three substitution s-triazine compounds and preparation method thereof

Technical field

The invention belongs to chemical field, is related to a kind of three new substitution s-triazine compounds and its preparation.

Background technology

S-triazine compound is widely used in the industries such as medicine, weaving, rubber, as antiseptic, insecticide, activity Dyestuff, fluorescent whitening agent, luminescent material, explosive and catalyst etc., its route of synthesis be mainly the ring of nitrile compounds it is poly- and Therefore, the three substitution s-triazine compounds for preparing novelty have important theory significance and reality to the modification of s-triazine side chain Application value.

The content of the invention

It is an object of the invention to provide a kind of three new substitution s-triazine compounds, general structure are as follows:

R in formula (III)1, R2Each stand alone as hydrogen, C1~C10 alkyl or C6~C10 aryl, or R1, R2With both it Between N combine the heterocycle to form C4~C8 containing N or containing N, O;It is preferred that R1, R2Each stand alone as hydrogen or methyl, or R1, R2With N between the two combines to form nafoxidine ring, piperidine ring or morpholine ring.R3, R4Each stand alone as hydrogen, C1~C10 alkyl or C6 ~C10 aryl;It is preferred that R3, R4Each stand alone as hydrogen or methyl.R5For C6~C10 aryl;Further R5For substituted-phenyl;It is preferred that R5 For 3,4- Dimethoxyphenyls, rubigan or p-bromophenyl.

It is a further object to provide the compound (III) preparation method, realized by following steps:

By the hydrochloride of the biguanide compound shown in formula (I) with 1,1- dibromoethylenes class compound shown in formula (II) are mixed Close and add in organic solvent, under the catalytic action of metallic copper, in the presence of part and alkali, stirred at a temperature of 60~130 DEG C Mix reaction 2~25 hours, after reaction terminates, three substitution compound in triazine class shown in formula (III) are made in reaction solution post processing.Instead Answer formula as follows:

The organic solvent is ethers;The metal copper catalyst is the halide of copper or the oxide of copper;The part For aromatic nitrogen heterocycle, carbonyl containing compound or amino acid;The alkali is inorganic base;1,1- dibromoethylene classizationes shown in formula (II) with The hydrochloride (not including Metformin) of biguanide compound shown in formula (I), metal copper catalyst, part, alkalescence The amount ratio of the material of material is 1:0.5~3.0:0.05~0.5:0.3~0.1:8.0~4.0.

Wherein R1, R2Each stand alone as hydrogen, C1~C10 alkyl or C6~C10 aryl, or R1, R2N between the two Combination forms the heterocycle of C4~C8 containing N or containing N, O;It is preferred that R1, R2Each hydrogen, methyl are stood alone as (not including R1, R2It is simultaneously Methyl, R3, R4It is simultaneously hydrogen atom;And R1, R2It is simultaneously hydrogen atom, R3, R4It is simultaneously methyl), or R1, R2With both it Between N combine to form nafoxidine ring, piperidine ring or morpholine ring.R3, R4Each stand alone as hydrogen, C1~C10 alkyl or C6~C10 Aryl;It is preferred that R3, R4Each stand alone as hydrogen or methyl.R5For C6~C10 aryl;It is preferred that R5For substituted-phenyl;Further preferred R5 For 3,4- Dimethoxyphenyls, rubigan or p-bromophenyl.

Described organic solvent is ethers;Preferably tetrahydrofuran and 1,4- dioxane;More preferably 1,4- bis- The ring of oxygen six.The volumetric usage of the organic solvent is generally calculated as with the quality of the 1,1- dibromoethylene class compounds shown in formula (II) 10~50mL/g.

Described metal copper catalyst is the halide of copper or the oxide of copper;Preferably cuprous iodide or cuprous oxide.

The part is aromatic nitrogen heterocycle, carbonyl containing compound or amino acid;Preferably 2,2 '-bipyridyl, ninhydrin or Glycine.

Described alkali is inorganic base;Preferably potassium phosphate.

In preparation method of the present invention, the post processing can be with the following method:After reaction terminates, reacting liquid filtering, Filter residue is washed with methanol, concentrates filtrate, column chromatography (dichloromethane:Methanol=50:1, V:V), washing containing target compound is collected De- liquid, is evaporated under reduced pressure, is dried to obtain target compound (III).

It is also another object of the present invention to provide the compound (III) to prepare the application in treating breast cancer medicines.

The preparation method for developing three novel substitution s-triazine compounds of structure of the present invention, the technological reaction condition Gently, easy to operate, cost is low, there is extensive prospects for commercial application.Three substitutions s-triazine chemical combination provided by the present invention Thing shows certain anti-breast cancer activity, is laid a good foundation for new medicament screen and exploitation, has preferable practical value.

Embodiment

Below will by embodiment, the present invention is further illustrated, but protection scope of the present invention not limited to this.

Embodiment 1:The preparation of compound (III-1)

Piperidines biguanide hydrochloride (0.2057g), 1,1- dibromo (3,4- dimethoxy) styrene are added in reaction vessel (0.1286g), cuprous iodide (0.0076g), 2,2 '-bipyridyl (0.0125g), potassium phosphate (0.5094g), in Isosorbide-5-Nitrae-dioxy six Mixed in ring (5mL), stirring reaction 13 hours in 110 DEG C of oil baths;After reaction terminates, filtering, filter residue is washed with methanol, concentration filter Liquid, column chromatography (dichloromethane:Methanol=50:1) R, is collectedfThe eluent of value 0.3~0.35, it is evaporated under reduced pressure, is dried to obtain mesh Mark compound III-1 (0.1067g, yield 81%).

1H NMR(500MHz,CDCl3):δ 6.99 (d, J=1.8Hz, 1H), 6.90 (dd, J=8.2,1.8Hz, 1H), 6.80 (d, J=8.2Hz, 1H), 5.16 (s, 2H), 3.87 (s, 3H), 3.86 (s, 3H), 3.75-3.73 (m, 6H), 1.66 (t, J =5.4Hz 2H), 1.61-1.49 (m, 4H).

Embodiment 2:

The amount of cuprous iodide is changed to 0.0048g, other operations are the same as embodiment 1, the amount of obtaining 0.013g, yield 10%.

Embodiment 3:

The amount of cuprous iodide is changed to 0.0189g, other operations are the same as embodiment 1, the amount of obtaining 0.0988g, yield 75%.

Embodiment 4:

The amount of piperidines biguanide hydrochloride is changed to 0.308g, other operations are with embodiment 1, the amount of obtaining 0.079g, yield 60%.

Embodiment 5:

The amount of piperidines biguanide hydrochloride is changed to 0.103g, other operations are with embodiment 1, the amount of obtaining 0.0105g, yield 8%.

Embodiment 6:

The amount of 2,2 '-bipyridyl is changed to 0.0076g, other operations are with embodiment 1, the amount of obtaining 0.0527g, yield 40%.

Embodiment 7:

The amount of 2,2 '-bipyridyl is changed to 0.0234g, other operations are with embodiment 1, the amount of obtaining 0.0724g, yield 55%.

Embodiment 8:

The amount of potassium phosphate is changed to 0.4246g, other operations are the same as embodiment 1, the amount of obtaining 0.0803g, yield 61%.

Embodiment 9:

The amount of potassium phosphate is changed to 0.8491g, other operations are the same as embodiment 1, the amount of obtaining 0.1001g, yield 76%.

Embodiment 10:

Reaction temperature is reduced to 60 DEG C, other operations are the same as embodiment 1, the amount of obtaining 0.0206g, yield 10%.

Embodiment 11:

Reaction temperature is increased to 130 DEG C, other operations are the same as embodiment 1, the amount of obtaining 0.0658g, yield 50%.

Embodiment 12:The preparation of compound (III-2)

Operation with embodiment 1, simply by piperidines biguanide hydrochloride change into nafoxidine biguanide hydrochloride (0.1917g, 1.00mmol), 2,2 '-bipyridyl changes ninhydrin (0.0128g, 0.08mmol) into, and target compound III-2 is made (0.0946g, yield 75%).1H NMR(500MHz,CDCl3):δ 6.99 (d, J=1.8Hz, 1H), 6.91 (dd, J=8.1, 1.8Hz, 1H), 6.79 (d, J=8.1Hz, 1H), 5.28 (s, 2H), 3.87 (s, 3H), 3.85 (s, 3H), 3.74 (s, 2H), 3.58 (t, J=6.4Hz, 2H), 3.47 (t, J=6.4Hz, 2H), 2.02-1.83 (m, 4H).

Embodiment 13:The preparation of compound (III-3)

Operation changes abitilguanide hydrochloride (0.2077g, 1.00mmol) into embodiment 1, simply piperidines biguanide hydrochloride, 2,2 '-bipyridyl changes ninhydrin (0.0128g, 0.08mmol) into, and target compound III-3 is made, and (0.1087g, yield are 82%).1H NMR(500MHz,CDCl3):δ 6.93 (d, J=1.6Hz, 1H), 6.88 (dd, J=8.2,1.6Hz, 1H), 6.80 (d, J=8.2Hz, 1H), 5.26 (s, 2H), 3.86 (s, 3H), 3.86 (s, 3H), 3.84-3.74 (m, 4H), 3.74 (s, 2H), 3.72–3.69(m,4H)。

Embodiment 14:The preparation of compound (III-4)

Operation simply changes piperidines biguanide hydrochloride into N, N, N with embodiment 1 ', N '-tetramethyl biguanide hydrochloride (0.1937g, 1.00mmol), 2,2 '-bipyridyl is changed to glycine (0.0060g, 0.08mmol), and target compound III- is made 5 (0.0546g, yields 43%).

1H NMR(500MHz,CDCl3):δ 7.07 (d, J=1.8Hz, 1H), 6.94 (dd, J=8.1,1.8Hz, 1H), 6.79 (d, J=8.1Hz, 1H), 3.88 (s, 3H), 3.86 (s, 3H), 3.76 (s, 2H), 3.13 (s, 12H).

Embodiment 15:The preparation of compound (III-5)

Operation changes 1,1-, bis- bromo- styrene into embodiment 1, simply 1,1- dibromos (3 ', 4 '-dimethoxy) styrene (0.1048g, 0.40mmol), change piperidines biguanide hydrochloride into abitilguanide hydrochloride (0.2077g, 1.00mmol), be made Target compound III-7 (0.0847g, yield 78%).

1H NMR(500MHz,CDCl3):δ 7.35 (d, J=7.3Hz, 2H), 7.31 (t, J=7.3Hz, 2H), 7.23 (t, J =7.2Hz, 1H), 5.24 (s, 2H), 3.81-3.79 (m, 6H), 3.72-3.69 (m, 4H).

Embodiment 16:The preparation of compound (III-6)

Operation changes 1,1- dibromos (4 '-chlorine) benzene into embodiment 1, simply 1,1- dibromos (3 ', 4 '-dimethoxy) styrene Ethene (0.1186g, 0.40mmol), change piperidines biguanide hydrochloride into abitilguanide hydrochloride (0.2077g, 1.00mmol), Target compound III-8 (0.0929g, yield 76%) is made.

1H NMR(500MHz,CDCl3):δ7.31–7.23(m,4H),5.35(s,2H),3.78–3.76(m,6H),3.72– 3.66(m,4H)。

Embodiment 17:The preparation of compound (III-7)

Operation changes 1,1- dibromos (4 '-bromine) benzene into embodiment 1, simply 1,1- dibromos (3 ', 4 '-dimethoxy) styrene Ethene (0.1363g, 0.40mmol), change piperidines biguanide hydrochloride into abitilguanide hydrochloride (0.2077g, 1.00mmol), Target compound III-9 (0.0882g, yield 63%) is made.

1H NMR(500MHz,CDCl3):δ 7.41 (d, J=8.3Hz, 2H), 7.22 (d, J=8.3Hz, 2H), 5.20 (s, 2H),3.78-3.75(m,6H),3.72–3.68(m,4H)。

Embodiment 18:Anti-breast cancer cell MDA-MB-231 biological activity tests

External anti-breast cancer cell MDA-MB-231 activity test methods:Mtt assay

A principles:Thiazolyl blue (MTT) is decomposed into bluish violet crystallization not soluble in water simultaneously by cell by mitochondria hydrolase It is deposited in cell, crystal can determine the suction of its light with enzyme-linked immunosorbent assay instrument by dmso solution at 490nm wavelength Receipts value, reflect the proliferative conditions and number change of cell indirectly.

B cells:Breast cancer cell MDA-MB-231 (is purchased from Chinese Academy of Sciences's Shanghai school of life and health sciences cell bank)

C experimental procedures:

1) preparation of sample:For solvable sample, dissolved per 1mg with 20 μ L DMSO, take 2uL dilute with 1000 μ L nutrient solutions Release, it is 100 μ g/mL to make concentration, then with nutrient solution serial dilution to concentration.

2) culture of cell

2.1) preparation of culture medium:Contain 800,000 units of Penicillin, 1.0g streptomysins, 10% inactivation in per 1000mL culture mediums Hyclone.

2.2) culture of cell:By tumor cell inoculation in culture medium, 37 DEG C are put, 5%CO2Cultivated in incubator, 3~ 5d is passed on.

3) inhibitory action of the determination sample to growth of tumour cell

Cell is digested with EDTA- pancreatin digestive juice, and 1 × 10 is diluted to culture medium5/ mL, it is added to 96 hole cell trainings Support in plate, per hole 100uL, put 37 DEG C, 5%CO2Cultivated in incubator.After being inoculated with 24h, sample that addition is diluted with culture medium, Per the μ L of hole 100, each concentration adds 3 holes, puts 37 DEG C, 5%CO2Cultivated in incubator, add 5mg/ after 72h in cell culture well ML MTT, per the μ L of hole 10,37 DEG C of incubation 4h to be put, DMSO is added, per the μ L of hole 150, is vibrated with oscillator, Shi Jia Za is completely dissolved, With ELIASA under 570nm wavelength colorimetric.With similarity condition with being free of sample, the medium culture containing same concentration DMSO it is thin Born of the same parents calculate LC50 (IC of the sample to growth of tumour cell as control50), as a result as shown in table 1.

Using breast cancer cell MDA-MB-231 as model, using cis-platinum as positive reference substance, determine what is prepared in embodiment Biphenol compound (III) sample is in vitro to the inhibitory action of breast cancer cell growth.As a result show, part of compounds (III) is right Experiment breast cancer cell MDA-MB-231 used has certain inhibitory action (the results detailed in Table 1).

IC of the compound of table 1 (III) to MDA-MB-23150(μM)

Test No. Compound IC50 1 III-1 9.06 2 III-5 0.66 3 III-8 1.22 4 Comparison medicine (cis-platinum) 8.21

Claims (4)

1. a kind of preparation method of three substitutions s-triazine compound, it is characterised in that realized by following steps:
By the hydrochloride of the biguanide compound shown in formula (I) with 1, the 1- dibromoethylene class compounds shown in formula (II) are mixed Close and add in organic solvent, under the catalytic action of metallic copper, in the presence of part and alkali, stirred at a temperature of 60~130 DEG C Mix reaction 2 ~ 25 hours, after reaction terminates, formula is made in reaction solution post processing(III)Three shown substitution compound in triazine class, instead Answer formula as follows:
The organic solvent is selected from tetrahydrofuran or Isosorbide-5-Nitrae-dioxane, and the volumetric usage of organic solvent is with shown in formula (II) The quality of 1,1- dibromoethylene class compound is calculated as 10 ~ 50mL/g;Described metal copper catalyst is selected from cuprous iodide or oxidation It is cuprous;The part is selected from 2,2 '-bipyridyl, ninhydrin or glycine;Described alkali is selected from potassium phosphate, shown in formula (II) 1,1- dibromoethylene class compound and formula(I)The hydrochloride of shown biguanide compound, metal copper catalyst, part, alkali The mass ratio of material is 1:0.5~3.0:0.05~0.5:0.3~0.1:4.0~8.0;
Wherein R1, R2Each stand alone as hydrogen, C1 ~ C10 alkyl or C6 ~ C10 aryl, or R1, R2N between the two combines to be formed The heterocycle of C4 ~ C8 containing N or containing N, O;R3, R4Each stand alone as hydrogen, C1 ~ C10 alkyl or C6 ~ C10 aryl;R5For 3,4- diformazans Phenyl, rubigan or p-bromophenyl.
2. preparation method according to claim 1, it is characterised in that formula(I)The hydrochloride of shown biguanide compound Do not include Metformin.
3. preparation method according to claim 1, it is characterised in that R1, R2Each stand alone as hydrogen, methyl;R3, R4Each solely Stand as hydrogen or methyl, and do not include R1, R2It is simultaneously methyl, R3, R4It is simultaneously hydrogen atom.
4. preparation method according to claim 1, it is characterised in that the post processing is with the following method:Reaction terminates Afterwards, reacting liquid filtering, filter residue are washed with methanol, concentration filtrate, column chromatography, and the volume ratio of dichloromethane and methanol is 50:1, receive Collect the eluent containing target compound, be evaporated under reduced pressure, be dried to obtain target compound(III).
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