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Substituted 1,4-dihydro-chromene [2, 3-b] pyrrole compound and preparation method thereof

A technology of dihydrobenzopyran and compound, applied in the directions of drug combination, organic chemistry, antitumor drug, etc., can solve the problems of long reaction time, use of expensive catalysts or reagents, no literature reports on the synthesis method, etc., and achieve post-processing Convenience, low price, high yield effect

Inactive Publication Date: 2015-12-02
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] Although there are many reports on the synthesis of benzopyranyl pyrrole compounds, there are still some problems in the known synthetic methods, such as long reaction time, expensive catalysts or reagents, etc.
In addition, the synthesis method of benzopyran[2,3-b]pyrrole compounds is hardly reported in the literature.

Method used

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  • Substituted 1,4-dihydro-chromene [2, 3-b] pyrrole compound and preparation method thereof
  • Substituted 1,4-dihydro-chromene [2, 3-b] pyrrole compound and preparation method thereof
  • Substituted 1,4-dihydro-chromene [2, 3-b] pyrrole compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1, ethyl 5-hydroxy-4-oxo-3-(4-methylphenyl)-1,4-dihydrobenzopyran[2,3-b]pyrrole-2-carboxylate (m1 )

[0048] Add 115.5mg (0.5mmol) of ethyl 2-azido-3-(4-methylphenyl)acrylate and 81.0mg (0.5mmol) of 4-hydroxycoumarin into the reaction flask, and then add DMF ( N,N-Dimethylformamide) 2.0ml, Mn(OAc) 2 4H 2 O24.5mg (0.1mmol), after the addition was completed, the reaction was stirred at 90°C for 12 hours, and the reaction was detected by TLC (petroleum ether:ethyl acetate=4:1 volume ratio). The result of the TLC detection reaction was the disappearance of ethyl 2-azido-3-(4-bromophenyl)acrylate, indicating that the reaction had ended.

[0049] After the reaction was finished, cool to room temperature, add 60ml of water, and extract the reaction solution three times with 3×20mL ethyl acetate, and the organic layer (at the upper layer) was combined and washed three times with 3×30mL saturated brine, and then washed with anhydrous sodium sulfate (2.0 g) drying for...

Embodiment 2

[0076] Example 2, ethyl 5-hydroxy-4-oxo-3-phenyl-1,4-dihydrochromen[2,3-b]pyrrole-2-carboxylate (m2)

[0077] Replace ethyl 2-azido-3-(4-methylphenyl)acrylate with ethyl 2-azido-3-phenylacrylate, the molar weight remains unchanged, and the rest is the same as in Example 1. 139.6 mg of ethyl 5-hydroxy-4-oxo-3-phenyl-1,4-dihydrochromen[2,3-b]pyrrole-2-carboxylate was obtained as a white powder product, with a yield of 80% .

[0078] Its structural formula is:

[0079]

[0080] Whitepowder; mp:200.4-201.6℃; 1 HNMR(500MHz,DMSO)δ11.47(s,1H),7.86–7.81(m,1H),7.77–7.73(m,3H),7.63–7.58(m,1H),7.57–7.57(m,2H) ,7.42(d,J=8.4Hz,1H),7.28–7.24(m,1H),3.83–3.74(m,2H),0.64(t,J=7.1Hz,3H). 13 CNMR (125MHz, CDCl 3 )δ194.2, 172.9, 170.9, 161.2, 157.3, 138.3, 131.9, 129.1, 128.4, 127.9, 125.2, 122.6, 120.8, 113.5, 105.1, 90.1, 60.3, 13.1. HRMS (ESI): m / zcalcdforC 20 h 15 NO 5 [M+H] + :350.1028,found:350.1028.

Embodiment 3

[0081] Example 3, 5-hydroxy-4-oxo-3-(3-methoxyphenyl)-1,4-dihydrobenzopyran[2,3-b]pyrrole-2-carboxylic acid ethyl ester ( m3)

[0082] Replace 2-azido-3-(4-methylphenyl)ethyl acrylate with 2-azido-3-(3-methoxyphenyl)ethyl acrylate, the molar weight remains unchanged, and the rest are the same In Example 1. Ethyl 5-hydroxy-4-oxo-3-(3-methoxyphenyl)-1,4-dihydrochroman[2,3-b]pyrrole-2-carboxylate was obtained as a white powder product 168.6 mg, yield 89%.

[0083]

[0084] Whitepowder; mp:166.2-167.4℃; 1 HNMR(500MHz,DMSO)δ11.45(s,1H),7.85–7.81(m,1H),7.77–7.74(m,1H),7.48–7.43(m,1H),7.41(d,J=8.4Hz ,1H),7.35–7.31(m,2H),7.28–7.24(m,1H),7.19–7.15(m,1H),3.83(s,3H),3.82–3.75(m,2H),0.64(t ,J=7.1Hz,3H). 13 CNMR (125MHz, CDCl 3 ( zcalcdforC 21 h 17 NO 6 [M+H] + :380.1134,found:380.1136.

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Abstract

The invention discloses a substituted 1,4-dihydro-chromene [2, 3-b] pyrrole compound. The structural formula is as shown in specifications. The invention further discloses a preparation method of the substituted 1,4-dihydro-chromene [2, 3-b] pyrrole compound. The preparation method includes the steps that olefine azido compounds and 4-hydroxycoumarin react for 8-12 hours at 80-100 DEG C under the existence of solvent and a metal catalyst; obtained reaction liquid is cooled to indoor temperature, then water and ethyl acetate are used for extraction, and an obtained organic layer is concentrated after being rinsed; obtained concentrate is subjected to silica column chromatography to obtain the substituted 1, 4-dihydro-chromene [2, 3-b] pyrrole compound. The compound is an anti-tumor lead compound.

Description

technical field [0001] The invention belongs to a synthesis method of a compound, and mainly relates to a substituted 1,4-dihydrobenzopyran[2,3-b]pyrrole compound and a preparation method thereof. Background technique [0002] Benzopyran compounds are a class of important compounds that widely exist in nature, and they have a wide range of biological and pharmacological activities, such as anti-tumor, anti-fungal, anti-virus, anti-oxidation, etc. Benzopyranopyrrole has various biological activities due to its skeleton, including multidrug resistance reversal activity, HIV-1 integrase inhibitory activity, cytotoxicity, etc., so it plays an important role in medicinal chemistry. [0003] Because of the important application value of benzopyranopyrrole compounds, their synthesis methods have been widely concerned. Existing reports mainly contain the synthesis of three classes of benzopyrrole compounds, wherein González et al. (Alberola, A.; álvaro, R.; Andrés, J.M.; Calvo, B.;...

Claims

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Application Information

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IPC IPC(8): C07D491/052A61P35/00
CPCC07D491/052
Inventor 章国林郭闪闪俞永平
Owner ZHEJIANG UNIV
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