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Dimeric indole alkaloid compounds, preparation method thereof and use thereof in preparation of antibacterial drugs

A dimer indole biological and compound technology, applied in antibacterial drugs, organic chemistry, pharmaceutical formulations, etc., can solve the problems of unseen synthetic methods and reports of their applications

Active Publication Date: 2019-04-19
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And so far, there is no report about the synthetic method and application of this class of compounds

Method used

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  • Dimeric indole alkaloid compounds, preparation method thereof and use thereof in preparation of antibacterial drugs
  • Dimeric indole alkaloid compounds, preparation method thereof and use thereof in preparation of antibacterial drugs
  • Dimeric indole alkaloid compounds, preparation method thereof and use thereof in preparation of antibacterial drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The preparation of embodiment 1 compound 1a:

[0037] (1) Dissolve 0.28g of ethylenediamine in 30ml of dichloromethane, add 0.47g of triethylamine, and dropwise add 1.50g of compound 2 (N,N'-di-Boc-N"-triflylguanidine dissolved in dichloromethane ). Stir the reaction at room temperature for 10-12h. Wash and extract 2 times with saturated sodium bicarbonate solution, wash and extract once with water and saturated saline respectively. The organic phase is dried with anhydrous sodium sulfate, filtered and concentrated, and the residue is passed through a silica gel column Chromatography (eluent: ethyl acetate: methanol: triethylamine (volume ratio) = 10:1:0.1) yielded compound 3a as a colorless oil.

[0038] (2) Compound 3a was dissolved in dichloromethane, and after adding aqueous sodium bicarbonate solution, cyanogen bromide dissolved in dichloromethane was added dropwise at zero degrees Celsius, then reacted and stirred at room temperature for 1-2h, and separated and ex...

Embodiment 2

[0043] The preparation of embodiment 2 compound 1b:

[0044] With reference to Example 1, ethylenediamine is replaced with 1,6-hexamethylenediamine in step (1). Compound 1b was obtained as a pale yellow oil.

[0045] 1 H NMR (400MHz, CD 3 OD)δ(ppm):7.54(d,1H,ArH),7.40(dd,2H,ArH),7.28(d,1H,ArH),7.23(s,1H,CH),7.13(t,1H,ArH ),7.07(t,1H,ArH),7.04(t,1H,ArH),7.02(t,1H,ArH),6.94(t,1H,ArH),6.73(s,1H,CH),4.36(s ,2H,CH 2 ), 4.14 (s,2H,CH 2 ), 3.79(t,2H,CH 2 ), 3.05(t,2H,CH 2 ), 1.52 (m,2H,CH 2 ), 1.43 (m,2H,CH 2 ), 1.27-1.21 (m,4H,CH 2 ).

Embodiment 3

[0046] The preparation of embodiment 3 compound 1c:

[0047] Referring to Example 1, ethylenediamine in step (1) was replaced with 1,5-pentanediamine, and indoleacetic acid in step (4) was replaced with 5-fluoro-indoleacetic acid. Compound 1c was obtained as a pale yellow oil.

[0048] 1 H NMR (400MHz, CD 3 OD)δ(ppm):7.34(d,1H,ArH),7.31(s,1H,CH),7.25(d,1H,ArH),7.23(d,1H,ArH),7.10(d,1H,ArH ),6.90(dd,1H,ArH),6.84(dd,1H,ArH),6.84(s,1H,CH),4.35(s,2H,CH 2 ), 4.12 (s,2H,CH 2 ), 3.82(t,2H,CH 2 ), 3.03(t,2H,CH 2 ), 1.58-1.48 (m,4H,CH 2 ), 1.31-1.27 (m,2H,CH 2 ).

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Abstract

The present invention belongs to the fields of organic synthesis and pharmaceutical chemistry. In particular, the present invention relates to a series of dimeric indole alkaloid compounds as shown instructural general formula I, a preparation method thereof and use thereof in preparation of antibacterial drugs. After in vitro activity screening, results show that the compounds have strong antibacterial activity, in particular have specific inhibitory effects on strains of gram-positive bacteria such as staphylococcus, bacillus and enterococcus, and related drug-resistant strains thereof, andcan be used as lead compounds for developing new antibacterial drugs.

Description

technical field [0001] The invention belongs to the fields of organic synthesis and pharmaceutical chemistry. Specifically, it relates to a class of dipolyindole alkaloid compounds, its preparation method and its application in the preparation of antibacterial drugs. After in vitro activity screening, the results show that these compounds have strong antibacterial activity, especially good inhibitory effect on drug-resistant strains of Staphylococcus aureus and Enterococcus, and can be used as a class of lead compounds for the development of new antibacterial drugs. Background technique [0002] Staphylococcus aureus (Staphylococcus aureus) is an important pathogenic bacteria, Gram-positive bacteria, belonging to the genus Staphylococcus (Staphylococcus). It is the most common pathogenic bacteria in human suppurative infection. It can cause local suppurative infection, pneumonia, pseudomembranous enteritis, pericarditis, etc., and even systemic infection such as sepsis and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14A61K31/4245A61P31/04
CPCC07D413/14A61K31/4245A61P31/04
Inventor 郭跃伟蓝乐夫李序文陈菲菲刘进
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI