New use of medicine containing benzophen [C] anthridine alkaloid and its derivatives

A technology of alkaloids and derivatives, applied in the field of preparing anti-hepatitis B virus drugs

Inactive Publication Date: 2007-12-12
成都军区昆明总医院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The above patent documents related to the preparation and application research of benzo[C]phenanthridine derivatives are limited to anti-tumor, anti-platelet aggregation, anti-arrhythmia and insecticidal effec

Method used

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  • New use of medicine containing benzophen [C] anthridine alkaloid and its derivatives
  • New use of medicine containing benzophen [C] anthridine alkaloid and its derivatives
  • New use of medicine containing benzophen [C] anthridine alkaloid and its derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: Extracting and separating monomeric alkaloids I-III and IX from Celandine.

[0025] Get the whole herb of celandine (Chelidonium majus) and adjust slightly according to the method introduced in references [2, 3]: 5 kg of medicinal materials are extracted three times with 70% ethanol containing 5% acetic acid, and the extracts are combined, concentrated and steamed under reduced pressure. Most of the ethanol was removed, and the acid water extract was treated with a conventional acid-base method. First, 5% hydrochloric acid was added to PH2, and extracted with petroleum ether. The resulting acid water layer (S-1) was extracted with chloroform to obtain 23g (L-1). Silica gel column chromatography, petroleum ether: chloroform (10:0 ~ 10:1.5) gradient elution, chelidonine (IX = 1.86g) and dihydrochelerythrine (II = 45mg).

[0026] The above acidic aqueous layer (S-2) extracted with chloroform was allowed to stand, and the precipitate was collected by filtration, ...

Embodiment 2

[0027] Example 2: Conversion from quaternary ammonium benzo[C]phenanthridine alkaloids to tertiary amine benzo[C]phenanthridine alkaloids.

[0028] According to the method of reference [4], get chelerythrine hydrochloride (20mg, 0.052mM) and be dissolved in 15ml 10% dilute hydrochloric acid, add zinc powder 0.3g under stirring at room temperature, continue to stir overnight, reaction mixture is washed with chloroform Extract (60ml×3), wash the extract with a small amount of acidic water (10% dilute hydrochloric acid), then wash to neutrality, recover chloroform, and recrystallize the residue with ethanol to obtain 14 mg of dihydrochelerythrine (yield 77% ). The obtained physical and chemical constants and spectral data are consistent with those obtained by extraction and separation of dihydrochelerythrine.

[0029] The conversion of other quaternary ammonium benzo[C]phenanthridine alkaloids into tertiary amine benzo[C]phenanthridine alkaloids can be prepared by a similar meth...

Embodiment 3

[0030] Example 3: Physicochemical and Spectroscopic Data of Monomeric Compounds.

[0031] Chelidonine hydrochloride (I): [C 21 h 18 NO 4 ] + , Yellow needle crystal, mp201-202 ℃, bismuth iodide potassium reaction is positive. IR ν max KBr (cm -1 ): 3380, 2920, 2824, 1642 (C≡N + ), 1575, 1450, 1364, 1250, 1100, 1035 (C-O-C), 970, 875, 825; UV (nm, logε): 228 (4.49), 274sh (4.54), 282 (4.62), 320 (4.26), 346sh(3.55); EIMS: m / z 348[M] + (100), 333(12), 318(5), 307(6), 290(5), 167(4), 154(38), 136(31), 124(4). 1 H-NMR (400MHz, DMSO-d 6 ): 4.07 (3H, s, OMe), 4.13 (3H, s, 3H, s, OMe), 4.93 (3H, s, 3H, s, N-Me), 6.22 (2H, s, 2H, s, - OCH 2 O-), 7.83 (1H, s, 1H, s, H-1), 8.24 (1H, d, J=9.0Hz, H-9), 8.26 (1H, s, H-4), 8.29 (1H, d, J=9.0 Hz, H-9), 8.80 (2H, d, J=9.0 Hz, H-11), 10.06 (1H, s).

[0032]Dihydrochelerythrine (II): off-white crystal, C 21 h 19 NO 4 , mp164-165 ° C, bismuth iodide potassium reaction was positive. EIMS: 349[M] + (100), 348 (80), 334 [M-Me] +...

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PUM

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Abstract

The invention discloses a new use of phenanthridine biologic alcali of general formula I containing coumarone and its derivant in preparing anti-hepatitis b virus medicament.The biologic alcali has tumor cell apoptosis inducing effect, has strong inhibiting activity against to such pathogen, has antiviral effect, and is expected for treating liver cancer, wherein R1 to R10, R12 and R13 is hydrogen, hydroxy, carbon chain or naphthenic base with 1-12 carbon atoms, alkoxyl or acyloxy group, benzyloxy, chlorine and other halogen atoms, amino group, methylol, aldehyde group, carbonyl, acetonyl, carboxy, sulacyloxy, 4-methyl-benzenesulfonyloxyl, arylsulfonyloxy, diphenylphosphonoxyl and -OCONH2; R11 is hydrogen, methyl or oxygen atom; R14 and R15 are respectively hydrogen or methyl.

Description

technical field [0001] The invention relates to a new application of benzo[C]phenanthridine alkaloids and their derivatives in the preparation of anti-hepatitis B virus drugs. Background technique [0002] Hepatitis B virus HBV infection is a worldwide health problem. Because HBV infection can lead to chronic hepatitis, liver cirrhosis and primary liver cancer, most patients with liver cancer have a history of chronic hepatitis, so HBV infection has become one of the nine major diseases that affect human life. According to statistics, 2 billion people in the world have been infected with HBV, 360 million chronic patients, and 520,000 deaths per year, of which 50,000 died of acute HBV patients, and 470,000 died of liver cirrhosis and liver cancer. my country is a high-incidence area of ​​hepatitis B. The infection rate of HBV population is 57.6%, and the hepatitis B surface antigen (HBsAg) positive persons are 9.75%. The current chronic hepatitis B in the country is about 30...

Claims

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Application Information

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IPC IPC(8): A61K31/58A61P31/20A61P1/16
Inventor 左国营徐贵丽赵益斌张青何洪静余巍王根春唐斌
Owner 成都军区昆明总医院
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