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Indole derivative and preparation method thereof

A compound, hydrate technology, applied in the field of new antibacterial compounds, can solve problems such as no obvious antibacterial effect

Active Publication Date: 2014-03-26
MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Tests on these derivatives showed that, except for the antibacterial effect of N-formyl noveltymycin, which was close to that of noveltycin, other derivatives had no obvious antibacterial effect [Su Shenghui et al. Pharmaceutical Industry, 1984, 139 (2): 17)]

Method used

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  • Indole derivative and preparation method thereof
  • Indole derivative and preparation method thereof
  • Indole derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0328] Example 1: 2-Carboxylic acid-3-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole (compound C)

[0329]

[0330] Step 1) Under nitrogen protection, slowly add tin tetrachloride (4.5ml, 36mmol) to a solution of 4-iodoindole (7.5g, 30mmol) in dichloromethane (75ml) at 0°C, react at room temperature for 30min, and then Join Ac 2 O (2.9g, 30mmol) and nitromethane (46.5ml), reacted at room temperature for 1h, quenched with ice water, filtered, the filter cake was washed with a small amount of ether, the organic layer was extracted with ethyl acetate, anhydrous Na 2 SO 4 After drying, the solvent was spin-dried and recrystallized with ethyl acetate and petroleum ether to obtain compound 3-acetyl-4-iodoindole (6.9 g, 78%).

[0331] 1 HNMR(500MHz,DMSO-d6)δ:12.07(s,1H),8.32(d,J=3.0Hz,1H),7.67(dd,J=7.5Hz,1.0Hz,1H),7.49(dd,J= 8.0Hz, 1.0Hz, 1H), 6.92(t, J=8.0Hz, 1H), 2.49(s, 3H). MS (ESI + )m / z:286.0[M+H] + .

[0332] Step 2) Under nitrogen protection, mix 3-acetyl-4-iodoi...

Embodiment 2

[0341] Example 2: Benzoyloxymethyl 3-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole-2-carboxylate (CV2)

[0342]

[0343] Under nitrogen protection, the racemic mixture 2-carboxylic acid-3-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole or (2R,3S)-2 -Carboxylic acid-3-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole (0.23g, 1mmol) and triethylamine (0.10g, 1mmol) dissolved In DMF solution (6ml), react at room temperature for 5min, then add chloromethyl benzoate (0.17g, 1mmol), react at room temperature for 24h, add ethyl acetate 50ml after the reaction, wash the ethyl acetate layer (80ml×3 ), the ethyl acetate layer was washed with anhydrous Na 2 SO 4 After drying, the solvent was spin-dried and recrystallized with ethanol and petroleum ether to obtain a racemic mixture of 3-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole-2-carboxylate Benzoyloxymethyl ester or (2R,3S)-3-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole-2-carboxylic acid benzene Formyloxymethyl ester...

Embodiment 3

[0345] Example 3: 3-(Indol-3-yl)-butyric acid (Compound 20)

[0346]

[0347] Sodium hydroxide (0.19g, 4.8mmol) was dissolved in water (50ml), and the racemic mixture 2-carboxylic acid-3-methyl-3,5-dihydro-2H-thiopyrano[ 4,3,2-cd]indole or (2R,3S)-2-carboxylic acid-3-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole Indole (1g, 4.3mmol), add freshly prepared Raney nickel (Raney nickel) (10g, wet weight, containing absolute ethanol) and water (50ml) to it, heat and reflux for 1 hour, cool and filter, and use 0.02% Wash with sodium hydroxide solution (20ml×2), combine the washing solution with the filtrate, add 0.2 g of activated carbon for decolorization, filter, acidify the filtrate with concentrated hydrochloric acid and extract with ether (20ml×3), wash the ether extract with water (10ml×3) , dried over night over anhydrous sodium sulfate, concentrated solvent and recrystallized with diethyl ether and petroleum ether to obtain yellow crystals, which is a racemic mixture of ...

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Abstract

The invention relates to a novel antibacterial compound, i.e. an indole derivative, a three-dimensional isomerism or medical salt, solvent compound or aquo-complex as well as a preparation method, a medicine composition containing the compound and an application of the compound in preparing an antibiotic drug.

Description

technical field [0001] The present invention relates to a new class of antibacterial compounds, namely a class of indole derivatives, their stereoisomers or their pharmaceutically acceptable salts or solvates or hydrates; methods for preparing these compounds, pharmaceutical compositions containing these compounds, Use of these compounds in the preparation of antibacterial drugs, the antibacterial drugs are preferably directed against bacillus or gram, more preferably against mycobacterium tuberculosis or gram-negative bacteria or gram-positive bacteria. Background technique [0002] The resistance of drug-resistant strains to antibiotics, especially multidrug resistance, seriously endangers the treatment of anti-infective diseases and has become one of the important public health problems of global concern. In recent years, infections caused by drug-resistant strains have been one of the main causes of high mortality from infectious diseases, such as methicillin-resistant S...

Claims

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Application Information

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IPC IPC(8): C07D495/04C07D495/16C07D491/16C07D491/052C07D209/18C07D471/04C07D487/04C07D209/26C07F9/6561A61K31/407A61K31/437A61K31/4985A61K31/405A61K31/519A61K31/5377A61K31/4178A61K31/675A61P31/04
CPCC07D209/18C07D209/26C07D471/04C07D487/04C07D491/06C07D491/16C07D495/06C07D495/16C07F9/6561
Inventor 刘宗英李卓荣金洁朱俊泰
Owner MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI