Sinomenine derivatives and preparation method and medical application thereof

A technology of sinomenine and derivatives, applied in the field of medicinal chemistry, can solve the problems of short biological half-life, anaphylactic shock, slow onset of action, etc.

Inactive Publication Date: 2010-12-01
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the use of sinomenine as a drug has side effects such as rash and anaphylactic shock caused by the release of histamine, and the biological half-life is short, the dosage is too large, and the onset of effect is slow

Method used

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  • Sinomenine derivatives and preparation method and medical application thereof
  • Sinomenine derivatives and preparation method and medical application thereof
  • Sinomenine derivatives and preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Dissolve sinomenine (660 mg, 2 mmol) in 20 mL of carbon tetrachloride, add bromosuccinimide (NBS) (445 mg, 2.5 mmol) under stirring, continue stirring for about 2 h, filter out insoluble matter, and distill the filtrate to Dry it on a silica gel column and elute with dichloromethane:methanol (20:1~10:1) to give 1-bromosinomenine 2 (384 mg) as a pale yellow solid with a yield of 47.2% and a melting point of 148-153°C.

[0029] Confirmation of the structure of compound 2:

[0030] Pale yellow powder, ESI-MS: m / z 408.1[M+H] + , 1 H-NMR (300MHz, CDCl 3 ): δ6.93(1H, s, H-2), 5.44(1H, d, J=2.1Hz, H-8), 4.34(1H, d, J=15.6Hz, H-5a), 3.82(3H ,s,3-OC H 3 ), 3.50 (3H, s, 7-OC H 3 ), 3.43 (1H, m, H-9), 3.16 (1H, br s, H-14), 3.02 (1H, d, J=19.2Hz, H-10a), 2.72 (1H, d, J=11.4 Hz, H-16a), 2.58 (1H, dd, J=18.9, 6.0Hz, H-10b), 2.51 (3H, s, N-C H 3 ), 2.50(1H, d, J=15.6Hz, H-5b), 2.11(1H, m, H-16b), 1.97-1.99(2H, m, 2×H-15).

Embodiment 2

[0032] Referring to Example 1, using sinomenine as a raw material and chlorosuccinimide (NCS) as a halogenation reagent, compound 1 was prepared. White powder,

[0033] ESI-MS: m / z 364.1[M+H] + .

Embodiment 3

[0035] Referring to Example 1, using sinomenine as a raw material and iodosuccinimide (NIS) as a halogenation reagent, Compound 3 was prepared. yellow powder,

[0036] ESI-MS: m / z 456.1[M+H] + .

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Abstract

The invention provides sinomenine derivatives and preparation methods and medical applications thereof and relates to the pharmaceutical chemistry field. The invention particularly relates to a sinomenine derivative with the structural general formula I. The invention also discloses the preparation method of the sinomenine derivative. The invention selects the 293 cell transfected by Phf-Kb-luc to test the inhibitory action of the compounds to NF-kB signal channel and the results show that most of the compounds have good inhibitory action. Therefore, the sinomenine derivatives can be used to prepare anti-inflammatory immune medicines.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a sinomenine derivative and a preparation method thereof. The invention also discloses the application of the compound in the preparation of an anti-inflammatory immune drug. Background technique [0002] Sinomenine (Sinomenine, structural formula 1) is an alkaloid monomer extracted from the traditional Chinese medicine Ivy vine (Editorial Committee of the State Administration of Traditional Chinese Medicine "Chinese Materia Medica", Chinese Materia Medica, 1999.1966-1968), and its medicinal use is mostly its hydrochloride . Traditional Chinese medicine has used it to treat rheumatic diseases for more than one thousand years. Sinomenine has a definite curative effect. At present, various dosage forms such as injections, capsules, tablets, and patches have been used clinically, mainly for the treatment of rheumatism, rheumatoid arthritis, ankylosing spondylitis, and glomerular ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/28A61K31/485A61P29/00A61P37/02
Inventor 汤建刘瑞江徐秀泉于小凤
Owner JIANGSU UNIV
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