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A kind of thiazolamide derivative and its antidepressant use

A technology for aniline and compounds, applied in the field of preparation of thiazolamine derivatives, to achieve the effects of mild conditions, good antidepressant activity, and simple preparation route

Active Publication Date: 2022-07-01
THE SECOND PEOPLES HOSPITAL OF SHENZHEN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, there are no antidepressants of thiazolamides on the market at present, so the development of new thiazolamides with antidepressant activity still has good application prospects

Method used

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  • A kind of thiazolamide derivative and its antidepressant use
  • A kind of thiazolamide derivative and its antidepressant use
  • A kind of thiazolamide derivative and its antidepressant use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 3-[(5-ethyl-4-phenylthiazol-2-yl)amino]benzoic acid

[0039] Step 1: 3-[(-4-phenylthiazol-2-yl)amino]benzoic acid

[0040]

[0041] Add 1.96g (0.01mol) 3-carboxyphenylthiourea, 1.99g (0.01mol) 2-bromo-1-phenylethanone and 15mL glacial acetic acid to a 100mL oblique reaction flask with a condenser, stir evenly, Heating to reflux, TLC (developing solvent: ethyl acetate: petroleum ether=4:1) monitoring the reaction progress, the reaction was about 24h. Remove the insoluble solids in the reaction flask while it is still hot, and rotate part of the solvent. It was put into a fume hood to cool at room temperature, the solid was precipitated, filtered, the obtained solid was dried, and 2.02 g of powder was weighed, and the yield was 68.2%. 1 H NMR (DMSO-D 6 , 400MHz), δ: 7.16 (s, 1H, CH-S), 7.30-8.24 (m, 9H, C 6 H 4 , C 6 H 5 ), 10.38 (s, 1H, COOH).

[0042] Step 2: Preparation of the compound of formula I

[0043]

[0044] Add (0.28g, 3mmol) aniline, ...

Embodiment 2

[0046] Example 2 Antidepressant activity test

[0047]In this experiment, the high-throughput selection method of fluorescent substance ASP was used to find compounds that directly act on or produce reuptake inhibitory effects through adenosine receptors. Fluorescent dye ASP+ is a neurotoxic compound that can be combined with monoamine transporters to enter cells and emit yellow fluorescence (the order of binding is dopamine transporter>adrenaline transporter>5-HT transporter). When there are other compounds that can bind to the transporter, it competes with ASP, thereby reducing the number of cells entering the cell, and the yellow fluorescence is weakened.

[0048] RBL cells are a cell line that can secrete histamine and 5-HT, and the cells are immortalized mast cells that can release the transmitters quantumly. And has the ability to re-uptake 5-HT.

[0049] CACO-2 cells are adenocarcinoma cell lines derived from human small intestine. Studies have shown that the cells ca...

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PUM

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Abstract

The invention discloses a thiazolamide derivative with antidepressant activity, which can be used for preparing antidepressant drugs, broadens the scope of existing antidepressant compounds, and can be used as a leading compound for further optimization. Compared with fluoxetine hydrochloride, the compounds of the present invention have better antidepressant activity. The compound of the present invention has a simple preparation route, mild conditions, and is easy for industrialized large-scale production.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, in particular to a series of thiazolamide derivatives, a preparation method and uses thereof. Background technique [0002] Depression is a clinically manifested mood disorder or affective disorder caused by various reasons. About 15% of patients are accompanied by suicidal tendencies, which have a great impact on social stability and economic development. It is currently believed that receptors play an important role in the pathogenesis of depression and the mechanism of antidepressants, and the related receptors include monoamine receptors, glutamate receptors, glucocorticoid receptors and neurokinin receptors. body etc. Monoamine receptors include serotonin (5-HT) receptors, adrenergic receptors and dopamine receptors, among which the 5-HT system is the most widely studied. [0003] Janssen Pharmaceuticals reported a thiazolamide derivative with antidepressant activity (CN101263130...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/42A61K31/426A61P25/24
CPCC07D277/42A61P25/24
Inventor 谭回李维平任力杰俞玉明高明
Owner THE SECOND PEOPLES HOSPITAL OF SHENZHEN
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