Novel tryptamine derivative and preparation method and application thereof

A derivative, tryptamine technology, applied in the field of medicine, can solve the problems of lack of anti-inflammatory activity research, in-depth research on anti-inflammatory structure-activity relationship, unclear curative effect and application, etc., to improve spatial memory and learning ability, pharmacokinetics, etc. The effect of optimal kinetic parameters

Pending Publication Date: 2020-05-08
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to these biological activity studies of this type of compound, we found that tryptamine hormones are spliced ​​with salicylic acid structure, an

Method used

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  • Novel tryptamine derivative and preparation method and application thereof
  • Novel tryptamine derivative and preparation method and application thereof
  • Novel tryptamine derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] N-(2-(1H-indol-3-yl)ethyl)-2-((3-chloro-2-methylphenyl)amino)benzamide (new tryptamine derivative 1): Add tryptamine ( Formula I, 0.60 mmol) (if formula I is hydrochloride, water and dichloromethane need to be added, the pH of the aqueous phase is adjusted to 11 for extraction, and dried), and 2.5 mL of solvent dichloromethane is added. Add EDCI condensation agent at room temperature, that is, 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.60mmol), and simultaneously add catalyst HOBt (1-hydroxybenzotriazole) (0.50mmol) , base triethylamine (1.2mmol), and 2-((3-chloro-2-methylphenyl)amino)benzoic acid (formula II, 0.50mmol) were added and reacted at room temperature for 8h. After the completion of the reaction as monitored by TLC, it was filtered with suction, and the white solid was washed repeatedly with dichloromethane. The organic phase was spin-dried, and the organic phase was dried over anhydrous magnesium sulfate. Purification by silica gel colum...

Embodiment 2

[0045] N-(2-(1H-indol-3-yl)ethyl)-3-hydroxy-2-naphthamide (new tryptamine derivative 2):

[0046] With the method of embodiment 1, tryptamine is formula (I) (formula I), 3-hydroxy-2-naphthamide is (formula II) yield 75%. 1 H NMR(400MHz,DMSO)δ12.13(s,1H),10.87(s,1H), 9.19(t,J=5.4Hz,1H),8.51(s,1H),7.84(d,J=8.2Hz ,1H),7.74(d,J=8.3Hz,1H),7.62(d,J=7.8Hz,1H),7.50(t,J=7.5Hz,1H),7.35(dd,J=11.6,6.0Hz ,2H), 7.28(s,1H),7.23(s,1H),7.08(t,J=7.5Hz,1H),7.00(t,J=7.4Hz,1H),3.66(dd,J=13.3, 7.0Hz, 2H), 3.03(t, J=7.3Hz, 2H). 13 C NMR(101MHz,DMSO)δ168.18, 155.64,136.38,136.11,129.54,128.78,128.30,127.32,126.67,125.88,123.76, 122.88,121.09,118.65,118.40,111.70,111.53,110.83,40.19,25.04.

Embodiment 3

[0048] N-(2-(1H-indol-3-yl)ethyl)-2-hydroxy-4-methylbenzamide (new tryptamine derivative 3): with the method of Example 1, tryptamine is formula (I) (formula I), 2-hydroxy-4-methylbenzamide is (formula II) yield 80%. 1 H NMR (400MHz, DMSO) δ12.73(s, 1H), 10.83(s, 1H), 8.87(t, J=5.4Hz, 1H), 7.73(d, J=8.0Hz, 1H), 7.58(d ,J=7.8Hz,1H),7.35(d,J=8.1Hz,1H),7.18(d,J=1.6Hz,1H),7.07(t,J=7.5Hz,1H),6.99(t,J =7.4Hz,1H), 6.70(d,J=9.2Hz,2H),3.57(dd,J=13.5,7.0Hz,2H),2.97(t,J=7.4Hz,2H),2.27(s,3H ). 13 C NMR (101MHz, DMSO) δ169.20, 160.45, 144.13, 136.34, 127.43, 127.29, 122.77, 121.04, 119.61, 118.36, 118.33, 117.62, 112.53, 111.70, 111.48, 319.90, 2

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Abstract

The invention discloses a novel tryptamine derivative. The novel tryptamine derivative is characterized in that the chemical structural formula of the novel tryptamine derivative is as shown in the specification. According to the invention, an intracerebral tryptamine hormone fragment with an anti-neuroinflammation effect and a non-steroidal anti-inflammatory drug salicylic acid and derivatives thereof are subjected to molecular combination; on one hand, COX effect can be inhibited; and on the other hand, the generation of iNOS and inflammatory factors and the activation of immune cells can beinhibited, and the occurrence and development of inflammations are jointly inhibited through multiple mechanisms. Meanwhile, carboxylic acid groups of salicylic acid non-steroidal anti-inflammatory drugs can be removed, so gastrointestinal side effects caused by acidity are reduced. On such a basis, a series of compounds are designed and synthesized; and enzyme inhibition tests, various immune cell tests and animal in-vivo experimental studies prove that the synthesized compounds have good anti-inflammatory and analgesic activity.

Description

technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to a tryptamine derivative compound and its preparation method, and the application of its salt in the preparation of anti-inflammatory and analgesic drugs, which can be used to prevent and / or treat peripheral inflammation and / or or drugs for central nervous system inflammation. Background technique [0002] Tryptamine hormones have attracted attention due to their wide range of pharmacological activities. For example, the neurotransmitters 5-hydroxytryptamine (5-HT) and melatonin in the brain have strong antioxidant and free radical scavenging properties, thereby acting as anti-inflammatory, Prevents mitochondrial damage and apoptosis. Among them, melatonin has been proven to inhibit NO production, regulate JNK activation, and Akt / ERK / CREB signaling disorders to improve synaptic dysfunction, memory impairment, neuroinflammation, and neurodegeneration. Asumatriptan and...

Claims

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Application Information

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IPC IPC(8): C07D209/14A61K31/4045A61P1/04A61P3/06A61P7/02A61P9/10A61P17/00A61P19/02A61P25/02A61P25/14A61P25/16A61P25/28A61P25/24A61P29/00A61P37/06A61P39/06
CPCC07D209/14A61P1/04A61P3/06A61P7/02A61P9/10A61P17/00A61P19/02A61P25/02A61P25/14A61P25/16A61P25/28A61P25/24A61P29/00A61P37/06A61P39/06
Inventor 王震石桃范晓红李俊芳
Owner LANZHOU UNIVERSITY
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