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Benzohetercyclic compound as well as preparation method and applications thereof

A technology of compounds and heterocycles, applied in the field of medicinal chemistry

Active Publication Date: 2011-10-19
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the research on tryptamine analogs is mainly concentrated in the field of mental diseases as ligands of 5-HT receptors. So far, there have been no reports on the anti-HBV and anti-HCV effects of tryptamine alkaloid monomers and their use in the treatment of hepatitis B and C.

Method used

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  • Benzohetercyclic compound as well as preparation method and applications thereof
  • Benzohetercyclic compound as well as preparation method and applications thereof
  • Benzohetercyclic compound as well as preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] Example 1 Extraction of tryptamine alkaloids from plants

[0107] The roots and stems (20kg) of Jiangxi Rutaceae Evodia rutaecarpa were extracted three times by percolation at room temperature with 95% ethanol, the extracts were combined and concentrated under reduced pressure to obtain ethanol extract, and the ethanol extract was suspended in water (3L) Sequentially extract with petroleum ether, chloroform, ethyl acetate and n-butanol (each 3L×3); 78g of the n-butanol extraction part is acidified with 2% hydrochloric acid, and the precipitate is removed by filtration, and the acidic water layer is alkalized with concentrated ammonia water, adjusted The pH is about 8-9, and then extracted with n-butanol until there is no alkaloid reaction in the n-butanol layer, and 6.7 g of total alkaloids are obtained; the sample is mixed with silica gel, and the gradient elution is performed by normal phase silica gel column chromatography (CHCl 3 -MeOH 50:1, 20:1, 12:1, 8:1, 5:1, 3:...

Embodiment 25

[0110] Example 25-Hydroxy-N 12 - Oxy-N,N-Dimethyltryptamine

[0111]

[0112] Reagents and conditions: (a) NaOMe, MeOH, formaldehyde solution (38%), NaCNBH 3 , AcOH, room temperature, 2h; (b) MCPBA (50%), CHCl 3 , 0°C, 5min.

[0113] Specific test operation:

[0114] (a) Under an argon atmosphere, dissolve 200mg of 5-hydroxytryptamine hydrochloride (0.94mmol) in 10ml of anhydrous methanol, cool in an ice bath, and add fresh sodium methoxide (20mgNa dissolved in 1ml of anhydrous methanol) while stirring. Adjust pH8-9, then add 0.22ml acetic acid (3.76mmol) to adjust pH5-6, then add 102mg sodium cyanoborohydride (1.88mmol), finally add dropwise 0.18ml (2.26mmol) of 38% aqueous formaldehyde solution, the reaction temperature rises to At room temperature, continue to stir for 2h (TLC detects the reaction process), after the reaction is complete, add 2mol / L Na dropwise 2 CO 3 Adjust the pH of the solution to about 8-9 to terminate the reaction, filter, and concentrate the ...

Embodiment 3

[0130] Example 3N-Methyl-N 12 - Amyltryptamine

[0131]

[0132] Reagents and conditions: (a) MeOH, Isovaleraldehyde, NaCNBH 3 , AcOH, 0°C, 1h; (b) formaldehyde solution (38%) (excess), room temperature, 8h.

[0133] Specific test operation:

[0134] (a) Dissolve 100mg of tryptamine (0.62mmol) in 5ml of methanol, cool in an ice bath, add 0.14ml of acetic acid (2.48mmol) under stirring to adjust the pH to 5-6, then add 78mg of NaCNBH 3 (1.24mmol), finally dropwise added 0.067ml (0.62mmol) of isovaleraldehyde (0.62mmol) methanol (20ml) solution under ice bath cooling, the dropwise addition time was greater than 1h, the reaction temperature was kept at 0°C and continued to stir for 1h, and TLC detected that the reaction was complete .

[0135] (b) The reaction solution of the above (a) step is not treated, and the stirring is continued at room temperature, 0.06ml (0.75mmol) of 38% formaldehyde solution is added, and the stirring is continued for 1.5h (TLC detection reactio...

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Abstract

The invention provides a non-nucleoside antiviral inhibitor, especially a benzohetercyclic compound shown by a general formula I or pharmaceutically acceptable salt or hydrate. The invention further provides a method for preparing the compound or the pharmaceutically acceptable salt or hydrate. Pharmacology tests show that the compound or salt or hydrate accepted on the pharmacy can effectively inhibit replication of HBV (hepatitis B virus) DNA (deoxyribonucleic acid) and HCV (hepatitis C virus) RNA (Ribonucleic acid), therefore, the invention further provides applications on preparing medicaments in preventing and / or treating viral infection, especially the HBV and the HCV. The general formula I is as follows.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a new class of non-nucleoside antiviral inhibitors, in particular to a class of benzoheterocyclic compounds or pharmaceutically acceptable salts or hydrates thereof; the invention also relates to such compounds or The preparation method of its pharmaceutically acceptable salt or hydrate and its use in the preparation of drugs for preventing and / or treating viral infection, especially hepatitis B virus (HBV) infection and hepatitis C virus (HCV) infection. Background technique [0002] Virus infection can cause a variety of diseases and seriously endanger human health and life. Among them, hepatitis virus infection is an internationally recognized therapeutic problem. Among hepatitis viruses, type B (HBV), type C (HCV) are the most serious. According to the statistics of the World Health Organization (WHO), there are about 2 billion people in the world who have been infected with...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/16C07D401/14C07D405/14C07D409/14C07D405/12C07D409/12C07D235/06A61K31/4045A61K31/4439A61K31/4184A61P31/20A61P31/14A61P1/16
CPCC07D209/14C07D209/16C07D235/06C07D401/14C07D405/12C07D405/14C07D409/12C07D409/14A61P1/16A61P31/14A61P31/20C07D235/14
Inventor 朱大元左建平曲世津段文虎王桂凤
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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