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A kind of benzimidazole compound with anti-hepatitis B virus activity and antibacterial activity and its synthesis method and application

A technology of benzimidazole and antibacterial activity, applied in the field of benzimidazole compounds, can solve the problems of easy recurrence, nucleoside drugs are prone to drug resistance, etc., and achieve the effects of good inhibitory activity, significant scientific significance and application prospect.

Active Publication Date: 2022-02-22
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, long-term use of nucleoside drugs is prone to drug resistance and relapse after drug withdrawal, which has become a clinical problem

Method used

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  • A kind of benzimidazole compound with anti-hepatitis B virus activity and antibacterial activity and its synthesis method and application
  • A kind of benzimidazole compound with anti-hepatitis B virus activity and antibacterial activity and its synthesis method and application
  • A kind of benzimidazole compound with anti-hepatitis B virus activity and antibacterial activity and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] The preparation of embodiment 1 (E)-1-propyl group-2-styryl-1H-benzimidazole (H-1)

[0074] method 1

[0075]

[0076] Dissolve o-phenylenediamine (108 mg, 1 mmol, compound A) and cinnamaldehyde (158 mg, 1.2 mmol, compound B) in DMF (3 mL), add sodium metabisulfite (57 mg, 0.3 mmol) as a catalyst, stir and heat to 165°C , Reaction 12h, the reaction is basically complete. The reaction solution was added with dichloromethane, washed with water (3×15 mL), washed with saturated brine (2×15 mL), and dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and compound C was obtained through column chromatography with a yield of 60.0%. Dissolve C (44mg, 0.2mmol) in toluene (3mL), add potassium tert-butoxide (22mg, 0.2mmol), and react with bromopropane (29mg, 0.24mmol) at 140°C for 12h. After the reaction was completed, dichloromethane was added, washed with water (3×15mL), washed with saturated brine (2×15mL), the organic phase was dried over ...

Embodiment 2

[0080] The preparation of embodiment 2 (E)-5,6-dichloro-1-propyl-2-styryl-1H-benzimidazole (H-2)

[0081] method 1

[0082]

[0083] Dissolve 4,5-dichloro-o-phenylenediamine (177mg, 1mmol, compound D) and cinnamaldehyde (158mg, 1.2mmol, compound B) in DMF (3mL), add sodium metabisulfite (57mg, 0.3mmol) as a catalyst , stirred and heated to 165°C, reacted for 12h, and the reaction was almost complete. The reaction solution was diluted with dichloromethane, washed with water (3×15 mL), washed with saturated brine (2×15 mL), and dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and compound H-3 was obtained through column chromatography with a yield of 56.0%. 1 H NMR (400MHz, DMSO-d 6 )δ: 7.82(s, 2H), 7.72(dd, J=18.1, 12.0Hz, 3H), 7.46(t, J=7.2Hz, 2H), 7.40(d, J=7.1Hz, 1H), 7.26( s,1H),7.22(s,1H); 13 C NMR (101MHz, DMSO-d 6 ) δ: 153.99, 136.42, 135.90, 129.68, 129.46, 127.71, 124.84, 117.31; HRMS(ESI): m / z[M+H] + calcd.for C 15 h 11 N ...

Embodiment 3

[0089] The preparation of embodiment 3 (E)-5,6-dichloro-1-benzenesulfonyl-2-styryl-1H-benzimidazole (H-4)

[0090] method 1

[0091]

[0092] H-3 (58mg, 0.2mmol) was dissolved in dichloromethane (3mL), DMAP (24mg, 0.2mmol) was added, and reacted with benzenesulfonyl chloride (42mg, 0.24mmol) at 50°C for 12h. After the reaction was completed, dichloromethane was added, washed with water (3×15 mL), washed with saturated brine (2×15 mL), and dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and the corresponding product H-4 was obtained by column chromatography with a yield of 68.0%. 1 H NMR (400MHz, CDCl 3 )δ: 8.21 (s, 1H), 7.98-7.80 (m, 4H), 7.75 (s, 1H), 7.63 (dd, J = 15.8, 7.1Hz, 3H), 7.55-7.38 (m, 6H); 13 C NMR (101MHz, CDCl 3 ) δ: 152.84, 142.07, 141.37, 137.79, 135.36, 135.06, 132.19, 130.09, 129.87, 129.67, 129.13, 129.08, 127.92, 126.82, 120.91, 115.31, 113.45M): HMS( + calcd.for C 21 h 15 N 2 o 2 SCl 2 :429.0226; found: 429...

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Abstract

The invention discloses a benzimidazole compound with anti-hepatitis B virus activity and antibacterial activity, and a synthesis method and application thereof. The structure of this benzimidazole compound is shown in general formula (I): the synthesis method of this benzimidazole compound is also disclosed. Also disclosed is the application of the benzimidazole compound with anti-hepatitis B virus activity and antibacterial activity in the preparation of anti-hepatitis B virus medicines. The benzimidazole compounds disclosed in the invention have certain anti-HBV biological activity and antibacterial activity, and the anti-HBV activity is comparable to that of clinical anti-HBV drug tenofovir. inhibitory activity. In terms of compound structure, synthesis method and biological activity, the present invention has significant scientific significance and application prospect for developing novel anti-hepatitis B innovative drugs and antibacterial drugs of new structural types.

Description

technical field [0001] The invention relates to a benzimidazole compound with anti-hepatitis B virus activity and antibacterial activity, a synthesis method and application thereof. Background technique [0002] Chronic hepatitis B virus (HBV) infection is the cause of many liver diseases such as hepatitis, cirrhosis and liver cancer. According to the report of the World Health Organization, there are as many as 240 million people with chronic hepatitis B virus infection worldwide, and about 786,000 people die of chronic HBV infection-related liver diseases every year. Although hepatitis B (hepatitis B) vaccination has significantly controlled new infections in my country, there are still about 80 million cases of chronic HBV infection in China, of which more than 20 million patients with chronic hepatitis B (chronic hepatitis B). Although TDF (Viread, tenofovir disoproxil fumarate), TAF (Vemlidy, tenofovir alafenamide fumarate) and other blockbuster anti-hepatitis B virus ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/08A61K31/4184A61P31/04A61P31/20
CPCA61P31/04A61P31/20C07D235/08
Inventor 鲁桂尤义鹏黄功彬张辉潘婷张革翟珮宏鲁家琪林桐陈晓娜温婷
Owner SUN YAT SEN UNIV
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