CN108546252A - Triazinone compounds and its preparation method and application - Google Patents
Triazinone compounds and its preparation method and application Download PDFInfo
- Publication number
- CN108546252A CN108546252A CN201810410175.8A CN201810410175A CN108546252A CN 108546252 A CN108546252 A CN 108546252A CN 201810410175 A CN201810410175 A CN 201810410175A CN 108546252 A CN108546252 A CN 108546252A
- Authority
- CN
- China
- Prior art keywords
- formula
- iii
- triazinone compounds
- preparation
- triazinone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 0 *NC(NC(N)=O)=N Chemical compound *NC(NC(N)=O)=N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic 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
- C07D251/14—Heterocyclic 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
- C07D251/16—Heterocyclic 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses one kind triazinone compounds and the preparation method and application thereof, methods as shown in formula (III) to be：Alcohol compound shown in formula (I) is mixed with dicyandiamidines hydrochloride shown in formula (II) and is added in organic solvent, under metal Ru catalyst effect, in the presence of alkaline matter, it is stirred to react at a temperature of 60~130 DEG C 15~27 hours, after reaction, obtain reaction solution, triazinone compounds shown in post-treated obtained formula (III).Technological reaction mild condition of the present invention, raw material is easy to get, easy to operate, at low cost, there is extensive prospects for commercial application.Triazinone compounds provided by the present invention can be applied to prepare treatment bone and flesh tumor medicine, lays a good foundation for new medicament screen and exploitation, has preferable practical value.
Description
(1) technical field
The present invention relates to a kind of triazinone compounds and its preparation method and application.
(2) background technology
Triazinone compounds are one of most common herbicides, are mainly used for preventing and kill off grassy weed and broad leaved weed,
In pesticide field using very extensive.1,3,5-triazines ketone is one of most important one kind compound in triazinone compounds,
The preparation method of such compound is less, mainly passes through S, S '-dimethyl-N-cyano carbimide di-sulfate amide derivatives
It is made under the conditions of sodium hydride, the preparation method complex steps, raw material is not easy to obtain, the structure list of prepared triazone derivatives
One, there is certain limitation.Therefore, the important reason of the preparation method of new, easy synthesis triazinone compounds is developed
By and practical significance.
(3) invention content
The present invention provides a new class of triazinone compounds and preparation method thereof in order to solve the problems existing in the prior art
And application.
The present invention adopts the following technical scheme that：
One kind triazinone compounds as shown in formula (III)：
In formula (III), R1Or R2Respectively stand alone as C1~C10Alkyl, C4~C10Aryl, wherein aryl are heteroaromatic, phenyl
Or by C1~4Alkyl, C1~4Alkoxy or halogen substitution phenyl.
Further, the preferably described R1Or R2Respectively stand alone as methyl, thienyl, phenyl or by methyl, methoxyl group, 3,4-
The phenyl that methylene dimethoxy, fluorine, chlorine or bromine replace.
Further, a kind of preparation method of the triazinone compounds as shown in formula (III) specifically in accordance with the following steps into
It is prepared by row：
Alcohol compound shown in formula (I) is mixed with dicyandiamidines hydrochloride shown in formula (II) and is added in organic solvent,
Under metal Ru catalyst effect, in the presence of alkaline matter, it is stirred to react 15~27 hours at a temperature of 60~130 DEG C, instead
After answering, reaction solution is obtained, triazinone compounds shown in post-treated obtained formula (III)；Alcohol shown in the formula (I)
Class compound is 1: 0.5 with the ratio between dicyandiamidines hydrochloride, metal Ru catalyst, amount of substance of alkaline matter shown in formula (II)
~1.5: 0.01~0.04: 1.0~2.5；The organic solvent is ethers or substituted benzene；The alkaline matter is organic
Alkali；The metal Ru catalyst be divalent ruthenium or trivalent ruthenium compound,
Formula (I) R1With formula (II) R2It is such as above-mentioned.
Further, the organic solvent is preferably tetrahydrofuran, Isosorbide-5-Nitrae-dioxane or toluene.
Further, the volumetric usage of the organic solvent is usually in terms of the quality of alcohol compound shown in formula (I)
For 5~20mL/mmol.
Further, the metal Ru catalyst is preferably ten dicarbapentaborane rutheniums, triphenylphosphine ruthenic chloride, two (triphenylphosphine) rings
Pentadiene ruthenic chloride or 1,5- cyclo-octadiene ruthenous chlorides.
Further, the alkaline matter is preferably potassium tert-butoxide.
In preparation method of the present invention, the post-processing approach of the reaction solution is：The post-processing approach of the reaction solution
For：After reaction, water is added into the reaction solution, is extracted with ethyl acetate, organic layer is merged, it is dry with anhydrous sodium sulfate
It is dry, filtering, concentrate filtrate, column chromatography for separation, the mixed liquor of the dichloromethane and methanol that are 30: 1 using volume ratio as eluant, eluent,
The eluent containing target compound is collected, vacuum distillation is dried to obtain triazinone compounds shown in formula (III).
Triazinone compounds of the present invention can be applied to prepare treatment bone and flesh tumor medicine.
Further, the triazinone compounds are preferably
Compared with prior art, the beneficial effects of the present invention are：
The present invention develops a kind of preparation method of triazinone compounds, and the technological reaction mild condition, raw material is easy to get,
It is easy to operate, it is at low cost, there is extensive prospects for commercial application.Triazinone compounds provided by the present invention show certain
Anti-human osteosarcoma cell activity, lays a good foundation for new medicament screen and exploitation, has preferable practical value.
Specific implementation mode
Below will by embodiment, the present invention is further illustrated, but the scope of the present invention is not limited thereto.
Embodiment 1：The preparation of compound (III-1)：
In the reaction vessel plus N- phenyl dicyandiamidines hydrochlorides (107.3mg, 0.50mmol), P-methoxybenzyl alcohol
(93.3mg, 0.75mmol), 1,5- cyclo-octadiene ruthenous chloride (2.8mg, 0.01mmol), potassium tert-butoxide (167.3mg,
1.50mmol), the mixing in Isosorbide-5-Nitrae-dioxane (4mL), reacts 27 hours at 100 DEG C, after reaction, obtains reaction solution, to
Add water in the reaction solution, be extracted with ethyl acetate, merge organic layer, dried with anhydrous sodium sulfate, filter, concentrates filtrate,
Column chromatography (dichloromethane:Methanol=30:1) R, is collectedfThe eluent of value 0.3~0.35, vacuum distillation, is dried to obtain targeted
Close object (III-1), 96.6mg, yield 65%.
1H NMR(500MHz,DMSO-d6) δ 12.09 (br, 1H), 10.02 (br, 1H), 8.21 (d, J=8.9Hz, 2H),
7.85-7.67 (m, 2H), 7.34 (t, J=7.3Hz, 2H), 7.13 (d, J=8.9Hz, 2H), 7.07 (t, J=7.3Hz, 1H),
3.87(s,3H).
Embodiment 2：
1,5- cyclo-octadiene ruthenous chlorides are changed to ten dicarbapentaborane rutheniums (6.7g, 0.01mmol), other operate same embodiment
Isosorbide-5-Nitrae 0mg, yield 27%.
Embodiment 3：
1,5- cyclo-octadiene ruthenous chlorides are changed to three (triphenylphosphine) ruthenous chlorides (9.5mg, 0.01mmol), other behaviour
Make with embodiment 1,66.9mg, yield 45%.
Embodiment 4：
1,5- cyclo-octadiene ruthenous chlorides are changed to two (triphenylphosphine) cyclopentadiene ruthenic chlorides (7.0mg, 0.01mmol),
Other operations are the same as embodiment 1,52mg, yield 35%.
Embodiment 5：
Solvent Isosorbide-5-Nitrae-dioxane is changed to tetrahydrofuran (15mL), is 60 DEG C by reaction temperature, other operations are the same as implementation
Example 1,31.2mg, yield 21%.
Embodiment 6：
Reaction temperature is increased to 130 DEG C, other operations are the same as embodiment 1,89.1mg, yield 60%.
Embodiment 7：
The amount of 1,5- cyclo-octadiene ruthenous chlorides is changed to 7.8mg, with embodiment 1,52mg, yield is for other operations
35%.
Embodiment 8：
The amount of 1,5- cyclo-octadiene ruthenous chlorides is changed to 2.7mg, with embodiment 1,22.3mg, yield is for other operations
15%.
Embodiment 9：
The amount of potassium tert-butoxide is changed to 83.6mg, other operations are the same as embodiment 1,53.5mg, yield 36%.
Embodiment 10：
The amount of potassium tert-butoxide is changed to 209.1mg, other operations are the same as embodiment 1,29.7mg, yield 20%.
Embodiment 11：
It will be changed in reaction time 15 hours, other operations are the same as embodiment Isosorbide-5-Nitrae 3.1mg, yield 29%.
Embodiment 12：
The amount of N- phenyl dicyandiamidines hydrochlorides is changed to 80.5mg, with embodiment 1,26.7mg, yield is for other operations
18%.
Embodiment 13：
The amount of N- phenyl dicyandiamidines hydrochlorides is changed to 241.4mg, 1.1mmol, other are operated with embodiment 1,37.2mg,
Yield is 25%.
Embodiment 14：The preparation of compound (III-2)
Operation only changes P-methoxybenzyl alcohol into 4- chlorobenzene methanols (107.2mg, 0.75mmol) with embodiment 1, makes
Obtain target compound (III-2), 91.0mg, yield 60%.1H NMR(500MHz,DMSO-d6)δ12.31(br,1H),
10.14 (br, 1H), 8.20 (d, J=6.9Hz, 2H), 7.95-7.54 (m, 4H), 7.41-7.24 (m, 2H), 7.17-7.01 (m,
1H).
Embodiment 15：The preparation of compound (III-3)
Operation with embodiment 1, only by P-methoxybenzyl alcohol change into 3,4- 3,5-dimethoxybenzoic alcohols (123.0mg,
0.75mmol), target compound (III-3), 135.3mg, yield 82% is made.
1H NMR(500MHz,DMSO-d6)δ12.11(br,1H),10.02(br,1H),8.26-7.69(m,4H),7.41-
7.25 (m, 2H), 7.16 (d, J=8.3Hz, 1H), 7.10-7.05 (m, 1H), 3.87 (s, 6H)
Embodiment 16：The preparation of compound (III-4)
Operation with embodiment 1, only by P-methoxybenzyl alcohol change into 2,3- 3,5-dimethoxybenzoic alcohols (126.5mg,
0.75mmol), target compound (III-4), 134.0mg, yield 87% is made.
1H NMR(500MHz,DMSO-d6) δ 11.86 (br, 1H), 10.12 (br, 1H), 7.84 (d, J=7.2Hz, 2H),
7.34 (t, J=7.2Hz, 2H), 7.29 (dd, J=7.0,2.8Hz, 1H), 7.24-7.21 (m, 2H), 7.07 (t, J=7.0Hz,
1H),3.88(s,3H),3.82(s,3H).
Embodiment 17：The preparation of compound (III-5)
Operation only changes P-methoxybenzyl alcohol into 2- thenyl alcohols (89.2mg, 0.75mmol) with embodiment 1, makes
Obtain target compound (III-5), 95.8mg, yield 71%.1H NMR(500MHz,DMSO-d6)δ12.32(br,1H),
10.00 (br, 1H), 8.47-8.20 (m, 1H), 8.02 (d, J=4.6Hz, 1H), 7.89-7.62 (m, 2H), 7.34 (t, J=
7.5Hz, 2H), 7.30 (t, J=4.6Hz, 1H), 7.08 (t, J=7.5Hz, 1H)
Embodiment 18：The preparation of compound (III-6)
Operation with embodiment 1, only by P-methoxybenzyl alcohol change into 2- methoxy benzyl alcohols (126.2mg,
0.75mmol), target compound (III-6), 102.2mg, yield 69% is made.
1H NMR(500MHz,DMSO-d6) δ 11.69 (br, 1H), 10.12 (br, 1H), 7.84 (d, J=7.8Hz, 2H),
7.75 (d, J=7.4Hz, 1H), 7.60 (t, J=7.8,1H), 7.34 (t, J=7.8Hz, 2H), 7.22 (d, J=7.4Hz,
1H), 7.12 (t, J=7.4Hz, 1H), 7.07 (t, J=7.4Hz, 1H), 3.89 (s, 3H)
Embodiment 19：The preparation of compound (III-7)
Operation only changes P-methoxybenzyl alcohol into 4- bromobenzenes methanol (140.5mg, 0.75mmol) with embodiment 1, makes
Obtain target compound (III-7), 113.0mg, yield 66%.1H NMR(500MHz,DMSO-d6)δ12.60(br,1H),
10.19 (br, 1H), 8.15 (d, J=7.2Hz, 2H), 7.92-7.53 (m, 4H), 7.36 (t, J=7.2Hz, 2H), 7.09 (t, J
=7.2Hz, 1H)
Embodiment 20：The preparation of compound (III-8)
Operation only changes P-methoxybenzyl alcohol into 3- chlorobenzene methanols (106.9mg, 0.75mmol) with embodiment 1, makes
Obtain target compound (III-8), 79.8mg, yield 53%.1H NMR(500MHz,DMSO-d6)δ12.33(br,1H),
10.16 (br, 1H), 8.34-8.21 (m, 1H), 8.15 (d, J=7.1Hz, 1H), 7.85-7.45 (m, 3H), 7.63 (t, J=
7.5Hz,1H),7.46-7.24(m,2H),7.17-7.01(m,1H).
Embodiment 21：The preparation of compound (III-9)
Operation only changes P-methoxybenzyl alcohol into 4- fluorophenyl methanols (91.4mg, 0.75mmol) with embodiment 1, makes
Obtain target compound (III-9), 106.1mg, yield 53%.1H NMR(500MHz,DMSO-d6)δ12.25(br,1H),
10.12 (br, 1H), 8.33-8.21 (m, 2H), 7.94-7.69 (m, 2H), 7.44 (t, J=7.8Hz, 2H), 7.36 (t, J=
7.2Hz, 2H), 7.09 (t, J=7.2Hz, 1H)
Embodiment 22：The preparation of compound (III-10)
Operation with embodiment 1, only by P-methoxybenzyl alcohol change into the sub- methoxy benzyl alcohol of 2,3- bis- (113.6mg,
0.75mmol), target compound (III-10), 122.3mg, yield 84% is made.
1H NMR(500MHz,DMSO-d6)δ12.07(br,1H),10.01(br,1H),8.06-7.58(m,4H),7.48-
7.24(m,2H),7.21-7.00(m,2H),6.18(s,2H).
Embodiment 23：The preparation of compound (III-11)
Operation with embodiment 1, only by N- phenyl dicyandiamidines hydrochlorides change into N- methyl amidino ureas hydrochloride (77.6mg,
0.50mmol), target compound (III-11), 45.5mg, yield 46% is made.
1H NMR(500MHz,DMSO-d6)δ11.85(br,1H),8.26(br,1H),8.1-7.93(m,2H),7.63-
7.53 (m, 3H), 2.79 (d, J=4.1Hz 3H)
Embodiment 24：The preparation of compound (III-12)
Operation only changes N- phenyl dicyandiamidines hydrochlorides into N- (4- aminomethyl phenyls) dicyandiamidines hydrochloride with embodiment 1
(77.6mg, 0.50mmol), P-methoxybenzyl alcohol are changed to 3- chlorobenzene methanols (109.9mg, 0.75mmol), and target chemical combination is made
Object (III-12), 74.5mg, yield 50%.
1H NMR(500MHz,DMSO-d6)δ12.29(br,1H),10.10(br,1H),8.34-8.21(m,1H),8.14
(d, J=8.9Hz, 1H), 7.73-7.60 (m, 4H), 7.16 (d, J=7.5Hz, 2H), 2.29 (s, 3H)
Embodiment 25：Anti-human osteosarcoma U 2OS biological activity test
External anti-human osteosarcoma cell (U2OS) activity test method：Mtt assay
Experimental procedure：
1) preparation of sample：For solvable sample, per 1mg with 20 μ L DMSO dissolvings, take 2uL dilute with 1000 μ L culture solutions
It releases, makes a concentration of 100 μ g/mL, then concentration is extremely used with culture solution serial dilution.
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
Fetal calf serum.
2.2) culture of cell：By tumor cell inoculation in culture medium, 37 DEG C are set, 5%CO2It is cultivated in incubator, 3~
5d is passed on.
3) inhibiting effect of the determination sample to growth of tumour cell
Cell EDTA- pancreatin digestive juices are digested, culture medium is used in combination to be diluted to 1 × 105/ mL is added to 96 hole cell trainings
It supports in plate, per hole 100uL, sets 37 DEG C, 5%CO2It is cultivated in incubator.After inoculation for 24 hours, the diluted sample of addition culture medium,
Per 100 μ L of hole, each concentration adds 3 holes, sets 37 DEG C, 5%CO2It is cultivated in incubator, 5mg/ is added after 72h in cell culture well
The MTT of mL sets 37 DEG C of incubation 4h, DMSO is added, per 150 μ L of hole, is vibrated with oscillator per 10 μ L of hole, and Shi Jia Za is completely dissolved,
With microplate reader under 570nm wavelength colorimetric.With similarity condition use be free of sample, the medium culture containing same concentration DMSO it is thin
Born of the same parents as a contrast, calculate sample to the inhibiting rate of growth of tumour cell, the results are shown in Table 1.
Using human osteosarcoma cell U2OS as model, determine the triazinone compounds (III-1) that are prepared in embodiment~
(III-12) 12 samples are in vitro to the inhibiting effect of human osteosarcoma cell's growth.The results show that the sample that this experiment is tested
In, compound (III-2), (III-3), (III-5), (III-6), (III-10) have to testing osteosarcoma U 2OS used
Certain inhibiting effect (the results detailed in Table 1).
Inhibiting rate of the 1 each compound of table to human osteosarcoma cell U2OS
| Compound | Inhibiting rate % | Compound | Inhibiting rate % |
| (III-1) | 30 | (II1-7) | 31 |
| (III-2) | 74 | (III-8) | 26 |
| (III-3) | 65 | (III-9) | 32 |
| (III-4) | 25 | (III-10) | 67 |
| (III-5) | 64 | (III-11) | 22 |
| (III-6) | 68 | (III-12) | 35 |
Claims (10)
1. a kind of triazinone compounds as shown in formula (III)：
In formula (III), R1Or R2Respectively stand alone as C1~C10Alkyl, C4~C10Aryl, wherein aryl be heteroaromatic, phenyl or by
C1~4Alkyl, C1~4Alkoxy or halogen substitution phenyl.
2. triazinone compounds as described in claim 1, it is characterised in that：The R1Or R2Respectively stand alone as methyl, thiophene
Pheno, phenyl or the phenyl replaced by methyl, methoxyl group, 3,4- methylenes dimethoxy, fluorine, chlorine or bromine.
3. the preparation method of triazinone compounds as described in claim 1, it is characterised in that：The method is according to as follows
It is prepared by step：
Alcohol compound shown in formula (I) is mixed with dicyandiamidines hydrochloride shown in formula (II) and is added in organic solvent, in metal
It under ruthenium catalyst effect, in the presence of alkaline matter, is stirred to react at a temperature of 60~130 DEG C 15~27 hours, reaction knot
Shu Hou, obtains reaction solution, triazinone compounds shown in post-treated obtained formula (III)；Alcohols shown in the formula (I)
It is 1 that object, which is closed, with the ratio between dicyandiamidines hydrochloride, metal Ru catalyst, amount of substance of alkaline matter shown in formula (II)：0.5~
1.5：0.01~0.04：1.0~2.5；The organic solvent is ethers or or substituted benzene；The alkaline matter is organic
Alkali；The metal Ru catalyst be divalent ruthenium or trivalent ruthenium compound,
4. method as claimed in claim 3, it is characterised in that：The organic solvent is tetrahydrofuran, Isosorbide-5-Nitrae-dioxane
Or toluene.
5. method as claimed in claim 3, it is characterised in that：The volumetric usage of the organic solvent is with shown in formula (I)
The amount of the substance of alcohol compound is calculated as 5~20mL/mmol.
6. method as claimed in claim 3, it is characterised in that：The metal Ru catalyst is ten dicarbapentaborane rutheniums, triphenylphosphine
Ruthenic chloride, two (triphenylphosphine) cyclopentadiene ruthenic chlorides or 1,5- cyclo-octadiene ruthenous chlorides.
7. method as claimed in claim 3, it is characterised in that：The alkaline matter is potassium tert-butoxide.
8. method as claimed in claim 3, it is characterised in that：The post-processing approach of the reaction solution is：After reaction, to
Add water in the reaction solution, be extracted with ethyl acetate, merge organic layer, dried with anhydrous sodium sulfate, filter, concentrates filtrate,
Column chromatography for separation, with volume ratio for 30:1 dichloromethane and the mixed liquor of methanol are eluant, eluent, it collects containing target compound
Eluent, vacuum distillation, is dried to obtain triazinone compounds shown in formula (III).
9. a kind of triazinone compounds as described in claim 1 are preparing the application in treating human osteosarcoma drug.
10. application as claimed in claim 9, it is characterised in that：The triazinone compounds are
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810410175.8A CN108546252A (en) | 2018-05-02 | 2018-05-02 | Triazinone compounds and its preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810410175.8A CN108546252A (en) | 2018-05-02 | 2018-05-02 | Triazinone compounds and its preparation method and application |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108546252A true CN108546252A (en) | 2018-09-18 |
Family
ID=63513260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810410175.8A Pending CN108546252A (en) | 2018-05-02 | 2018-05-02 | Triazinone compounds and its preparation method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108546252A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110511214A (en) * | 2019-06-28 | 2019-11-29 | 浙江工业大学 | Two amidos replace heteroaromatic class compound and its preparation method and application |
| CN112250639A (en) * | 2020-11-19 | 2021-01-22 | 浙江工业大学 | Heterocyclic substituted arylamine compound and preparation method and application thereof |
| CN114031569A (en) * | 2021-11-30 | 2022-02-11 | 江苏剑牌农化股份有限公司 | Preparation process of triazone |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105384702A (en) * | 2015-12-11 | 2016-03-09 | 浙江大学 | Tri-substituted sym-triazine compound and preparation method thereof |
| CN105399695A (en) * | 2015-12-11 | 2016-03-16 | 浙江大学 | Triazine-kind compounds, preparation method and applications |
| CN105753801A (en) * | 2016-03-25 | 2016-07-13 | 浙江工业大学 | Preparation method of s-triazine compound |
| CN105820133A (en) * | 2016-03-25 | 2016-08-03 | 浙江工业大学 | Polysubstitution s-triazine compound and preparing method and application thereof |
-
2018
- 2018-05-02 CN CN201810410175.8A patent/CN108546252A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105384702A (en) * | 2015-12-11 | 2016-03-09 | 浙江大学 | Tri-substituted sym-triazine compound and preparation method thereof |
| CN105399695A (en) * | 2015-12-11 | 2016-03-16 | 浙江大学 | Triazine-kind compounds, preparation method and applications |
| CN105753801A (en) * | 2016-03-25 | 2016-07-13 | 浙江工业大学 | Preparation method of s-triazine compound |
| CN105820133A (en) * | 2016-03-25 | 2016-08-03 | 浙江工业大学 | Polysubstitution s-triazine compound and preparing method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| JEFFREY P.WHITTEN ET AL: "rapid microscal synthesis, a new method for lead optimization using robotics and solution phase chemistry:application to the synthesis and optimization of cortcotropin-releasing factor,receptoe antagonists", 《J.MED.CHEM.》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110511214A (en) * | 2019-06-28 | 2019-11-29 | 浙江工业大学 | Two amidos replace heteroaromatic class compound and its preparation method and application |
| CN112250639A (en) * | 2020-11-19 | 2021-01-22 | 浙江工业大学 | Heterocyclic substituted arylamine compound and preparation method and application thereof |
| CN112250639B (en) * | 2020-11-19 | 2022-05-24 | 浙江工业大学 | Heterocyclic substituted arylamine compound and preparation method and application thereof |
| CN114031569A (en) * | 2021-11-30 | 2022-02-11 | 江苏剑牌农化股份有限公司 | Preparation process of triazone |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Zhu et al. | Design, synthesis, and evaluation of chalcone analogues incorporate α, β-Unsaturated ketone functionality as anti-lung cancer agents via evoking ROS to induce pyroptosis | |
| Singh et al. | 1, 2, 3-Triazole tethered β-lactam-chalcone bifunctional hybrids: synthesis and anticancer evaluation | |
| EP3517534B1 (en) | Compounds useful for treating cancer | |
| CN108546252A (en) | Triazinone compounds and its preparation method and application | |
| Khanye et al. | Synthesis and in vitro antimalarial and antitubercular activity of gold (III) complexes containing thiosemicarbazone ligands | |
| CN104010501B (en) | Containing SRC homologous region 2 albumen Tyrosine phosphatase-1 synergist and methods of treatments thereof | |
| CN105399695B (en) | Compound in triazine class and its preparation method and application | |
| CN106432229B (en) | One kind is used for the compound for treating or preventing hyperuricemia or gout | |
| CN105384702B (en) | Three substitution s-triazine compounds and preparation method thereof | |
| CN108752284A (en) | Two amido-s- compound in triazine class of one kind and its preparation method and application | |
| Kalaiarasi et al. | para metallation of 3-acetyl-chromen-2-one Schiff bases in tetranuclear palladacycles: focus on their biomolecular interaction and in vitro cytotoxicity | |
| CN108658962A (en) | 3- substituted cumarins Furazan Derivatives and its purposes in preparing anti-multidrug resistance of tumor drug | |
| CN109369724A (en) | A kind of organoarsenium compound and application thereof | |
| CN104109115A (en) | Phenylpropionic acid compounds chained by nitrogen-containing heterocyclic rings, pharmaceutical composition, preparation method, and application thereof | |
| CN109053612A (en) | A kind of phenethyl replaces 1,3,5- compound in triazine class and its preparation method and application | |
| Habala et al. | Synthesis and structure-activity relationships of mono-and dialkyl-substituted oxaliplatin derivatives | |
| CN108794414A (en) | The s-triazine compound of aromatic amide substitution and preparation and application | |
| WO2020192348A1 (en) | Phenyl allylidene cyclohexenone derivatives and preparation method and use | |
| Malbari et al. | Structure-aided drug development of potential neuraminidase inhibitors against pandemic H1N1 exploring alternate binding mechanism | |
| CN110511214A (en) | Two amidos replace heteroaromatic class compound and its preparation method and application | |
| CN106214677A (en) | The application in preparing antitumor drug of a kind of substituted single carbonyl curcumin compounds containing pi-allyl | |
| CN109516959A (en) | 2- fragrant amino -4- substituted uracil derivative and its application in preparation of anti-tumor drugs | |
| CN108840829A (en) | A kind of preparation method of 4- aryl -1,3,5- triazine -2- ketone compounds | |
| CN104725372B (en) | Tetracyclic indole alkaloid derivative as well as preparation method and application thereof | |
| CN108129325A (en) | A kind of nitrogenous diphenyl ethylene derivatives of fluoro and its preparation method and application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20180918 |
|
| RJ01 | Rejection of invention patent application after publication |