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Thiazole dihydronaphthalene derivatives and application thereof in metabolic diseases

A technology of thiazole dihydronaphthalene derivatives, which is applied in the field of medicine, can solve the problems of large side effects and weak research on TGR5 agonists, and achieve the effect of great research value

Inactive Publication Date: 2020-07-24
邱曲真
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, most of the TGR5 agonists under research are bile acid analogs, which are steroidal compounds with relatively high side effects; research on non-steroidal TGR5 agonists is relatively weak

Method used

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  • Thiazole dihydronaphthalene derivatives and application thereof in metabolic diseases
  • Thiazole dihydronaphthalene derivatives and application thereof in metabolic diseases
  • Thiazole dihydronaphthalene derivatives and application thereof in metabolic diseases

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] (1) Preparation of 1-bromo-3,4-dihydronaphthalene-2-carbaldehyde

[0028] Add 2.1 mL (30.0 mmol) of N,N-dimethylformamide to 10 mL of chloroform. After cooling to 0°C in an ice bath, slowly add 2.8 mL (27.0 mmol) of phosphorus tribromide and continue to maintain 0°C and stir for 2 hours. 1.5 g (10.0 mmol) of 1-tetralone was added in batches, and the temperature was raised to room temperature to react for 6 hours. TLC detects the completion of the reaction, the reaction solution is slowly poured into ice water, and the pH of the reaction solution is adjusted to 8-9 with sodium bicarbonate. Extract with dichloromethane, combine the organic phases, wash the organic phases with saturated brine, and dry overnight with anhydrous sodium sulfate. The desiccant was filtered off, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 0.91 g of a yellow oily substance with a yield of 38.4%. MS (ESI) m / z...

Embodiment 2

[0038]

[0039] 1 H-NMR (400MHz, DMSO-d 6 )δ9.14(s,1H),8.44(s,1H),7.30-7.18(m,4H), 7.08-7.02(m,2H),6.90-6.88(m,1H), 4.36(t,J= 7.2Hz, 2H), 4.05 (t, J = 7.2Hz, 2H), 3.12 (t, J = 7.1Hz, 2H), 2.95 (t, J = 7.0 Hz, 2H).MS(ESI) m / z 393.1 [M+H] + .

Embodiment 3

[0041]

[0042] 1 H-NMR (400MHz, DMSO-d 6 )δ9.13(s,1H),8.45(s,1H),7.38-7.24(m,5H), 7.08-7.04(m,2H), 4.36(t,J=7.2Hz,2H),4.07(t ,J=7.3Hz,2H),3.11(t,J=7.3 Hz,2H),2.92(t,J=7.2Hz,2H).MS(ESI)m / z 409.2[M+H] + .

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Abstract

The invention belongs to the technical field of medicines, provides a thiazole dihydronaphthalene derivative shown in the following general formula and a preparation method thereof, and further discloses application of the thiazole dihydronaphthalene derivative in activating TGR5 activity and treating or preventing diseases related to TGR5 activity regulation.

Description

Technical field [0001] The present invention belongs to the technical field of medicine, and relates to a thiazole dihydronaphthalene derivative and a preparation method and application thereof. Specifically, the derivative can activate TGR5 activity and can be used to treat or prevent diseases related to the regulation of TGR5 activity. Background technique [0002] TGR5 is a G protein coupled receptor, also known as GPBAR1, BG37, M-BAR and so on. It is mainly expressed in lung, spleen, intestine and monocytes. The amino acid sequence of human TGR5 has 86%, 90%, 82% and 83% similarity with the corresponding sequences of cow, rabbit, rat and mouse respectively. When TGR5 is activated, it can cause the level of cAMP in the cell to increase, thereby promoting the increase of GLP-1 secreted by intestinal cells, which in turn has a hypoglycemic effect. [0003] TGR-5 receptor is involved in the regulation of blood glucose homeostasis, immune system, liver and gallbladder function, gas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/10A61K31/538A61K31/4725A61P3/10A61P3/04A61P3/00A61P1/16
CPCA61P1/16A61P3/00A61P3/04A61P3/10C07D417/10
Inventor 邱曲真
Owner 邱曲真
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