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Triazine compound as well as preparation method and application thereof

A technology of triazine compounds and compounds, applied in organic chemistry, drug combination, nervous system diseases, etc., can solve the problems of lower learning and memory ability, increase learning and memory, etc., and achieve the effect of obvious activity-concentration dose-effect relationship

Inactive Publication Date: 2017-10-31
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] According to literature reports, α7 nicotinic acetylcholine receptor positive allosteric modulators (PAM) have the effect of increasing learning and memory. Experiments show that mice lacking α7nAChR subunit are compared with the control group containing α7nAChR subunit mice. Decreased learning and memory ability in water maze experiment

Method used

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  • Triazine compound as well as preparation method and application thereof
  • Triazine compound as well as preparation method and application thereof
  • Triazine compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Preparation of 4-chloro-N-phenyl-6-(4-methylphenylthio)-1,3,5-triazin-2-amine (Code: PG-B-00)

[0027] 1. Synthesis of 4,6-dichloro-N-phenyl-1,3,5-triazin-2-amine (Ab1)

[0028]

[0029] Compound A (562mg, 3mmol) was placed in 4ml of THF, slowly added dropwise under ice-cooling a THF solution (2ml) dissolved in Compound b1 (281mg, 3mmol) and triethylamine (310mg, 3mmol), and slowly raised to room temperature, Stir overnight. Tetrahydrofuran was distilled off under reduced pressure, water was added, ethyl acetate was extracted three times, the ethyl acetate layers were combined, washed with saturated brine, spin-dried, mixed, and separated by silica gel column chromatography (petroleum ether: ethyl acetate) to obtain 410 mg of white solid , denoted as Ab1, yield 56.9%.

[0030] 2. Synthesis of 4-chloro-N-phenyl-6-(4-methylphenylthio)-1,3,5-triazin-2-amine (No.: PG-B-00)

[0031]

[0032] Compound Ab1 (247 mg, 1 mmol) was dissolved in 4 ml of tetrahyd...

Embodiment 2

[0033] Example 2: Preparation of 4-chloro-N-(2-fluorophenyl)-6-(4-methylphenylthio)-1,3,5-triazin-2-amine (Code: PG-B-29)

[0034] 1. Synthesis of 4,6-dichloro-N-(2-fluorophenyl)-1,3,5-triazin-2-amine (Ab2)

[0035]

[0036] The synthesis method is the same as that of compound Ab1. The white solid is denoted as Ab2, and the yield is 11%.

[0037] 2. Synthesis of 4-chloro-N-(2-fluorophenyl)-6-(4-methylphenylthio)-1,3,5-triazin-2-amine (No.: PG-B-29)

[0038]

[0039] The synthesis method is the same as compound PG-B-00. White solid, recorded as PG-B-29, yield 52.8%. 1 H NMR (400MHz, CDCl 3 )δ7.50(d, J=7.7Hz, 3H), 7.38(t, J=8.1Hz, 1H), 7.30(d, J=7.5Hz, 2H), 7.08–6.91(m, 2H), 6.62( t,J=7.4Hz,1H),2.50(s,3H). 13 C NMR (101MHz, CDCl 3 )δ185.63, 168.76, 162.30, 153.56, 151.12, 140.36, 136.11, 130.36, 125.43, 124.18, 123.93, 123.76, 121.29, 114.74, 21.52. + 347.0528; found value 347.0530.

Embodiment 3

[0040] Example 3: Preparation of 4-chloro-N-(3-fluorophenyl)-6-(4-methylphenylthio)-1,3,5-triazin-2-amine (Code: PG-B-40)

[0041] 1. Synthesis of 2,4-dichloro-6-(4-methylphenylthio)-1,3,5-triazine (Ac1)

[0042]

[0043] Put compound A (9.336g, 50mmol) in 100ml of tetrahydrofuran, add compound c1 (6.231g, 50mmol) and 10ml of supersaturated aqueous solution of sodium bicarbonate (6.312g, 75mmol) under ice-cooling, slowly warm to room temperature, and stir overnight. Subsequent operations were the same as for compound Ab1 to obtain 6.420 g of white needle-like crystals, denoted as Ac1, with a yield of 47.4%.

[0044] 2. Synthesis of 4-chloro-N-(3-fluorophenyl)-6-(4-methylphenylthio)-1,3,5-triazin-2-amine (No.: PG-B-40)

[0045]

[0046] Compound Ac1 (272mg, 1mmol) was dissolved in 4ml of tetrahydrofuran, slowly added dropwise under ice-cooling a THF solution (2ml) of compound b3 (131mg, 1.2mmol) and triethylamine (110mg, 1.1mmol), and slowly rose to room temperature, st...

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Abstract

The invention provides a triazine compound shown as a chemical formula (I) and a preparation method thereof as well as an application of the triazine compound in preparing drugs for treating central nervous system diseases. In the formula, R1 is selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, halogen-containing C1-C4 alkyl or halogen-containing C1-C4 alkoxy, and n is equal to 1-2; R2 is selected from C1-C6 alkyl, benzyl, phenyl, pyridine, benzothiazole, and phenyl substituted by one or more of halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthiol, C1-C4 alkylamides and hydroxyl; and R3 is selected from halogen, hydrazine, C1-C4 alkanes hydrazide, arylhydrazine, benzothiazolyl sulfonyl, thiophenyl, benzylthio, and thiophenyl substituted by one or more of halogen, C1-C4 alkyl and C1-C4 alkoxy.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a triazine compound, a preparation method thereof, and an application thereof in preparation of medicines for treating central nervous system diseases. Background technique [0002] Alzheimer's disease, also known as Alzheimer's disease, is a progressive and fatal neurodegenerative disease. Symptoms and behavioral disturbances. Many studies have clearly shown that acetylcholine deficiency and reduced expression of nicotinic acetylcholine receptors (nAChRs) in the brain of AD patients are common phenomena. [0003] According to literature reports, α7 nicotinic acetylcholine receptor positive allosteric modulators (PAM) have the effect of increasing learning and memory. Experiments show that mice lacking α7nAChR subunit compared with the control group containing α7nAChR subunit mice, The ability to learn and remember is reduced in the water maze experiment. The mode of action of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/42C07D251/46C07D251/52C07D401/12C07D417/14A61P25/00A61P25/28A61P25/16
Inventor 王克威孙崎彭耕杨洮乙黄晓敏
Owner PEKING UNIV