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Dialkyl and diaryl tetrasubstituted heterocyclic compounds, preparing process and use thereof

A kind of heterocyclic compound and tetra-substituted technology, which is applied in the field of preparation of diaryl tetra-substituted heterocyclic compounds, dialkyl, and can solve problems such as dialkyl that have not yet been seen

Inactive Publication Date: 2005-06-22
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the existing literature, the report of the dialkyl, diaryl four-substituted heterocyclic compound of the present invention and its use for anticancer drugs and COX-2 inhibitor drugs have not been seen so far

Method used

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  • Dialkyl and diaryl tetrasubstituted heterocyclic compounds, preparing process and use thereof
  • Dialkyl and diaryl tetrasubstituted heterocyclic compounds, preparing process and use thereof
  • Dialkyl and diaryl tetrasubstituted heterocyclic compounds, preparing process and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Synthesis of 2-(3-bromo-4-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-3,4-dimethylthiophene

[0098] (A) Preparation of o-bromoanisole (1)

[0099] In a round bottom flask equipped with a reflux condenser and a magnetic stirring device, 60 ml of 37% KOH aqueous solution and 50 ml of o-bromophenol were added at room temperature. The mixture was heated to 85°C with sufficient stirring and kept for 0.5 hours, and then sulfuric acid was added dropwise. 41ml of methyl ester, keep the pH of the reaction solution> 8, and continue the reaction for 48 hours. After the reaction was completed, it was extracted with ether, the organic layer was washed with a 10% KOH aqueous solution, and the solvent was evaporated to obtain a pale yellow liquid o-bromoanisole with a yield of 86%.

[0100] (B) Preparation of 3-bromo-4-methoxypropiophenone (2)

[0101] Add 200ml of dried CHCl to a dry round bottom flask 3 And 86g AlCl 3 , Keep the temperature of the reaction solution at 0~5℃ with an ice wa...

Embodiment 2

[0118] Preparation of 2-(3-bromo-4-methoxyphenyl)-3,4-dimethyl-5-(3,,4,5-trimethoxyphenyl)furan (9)

[0119] In a round bottom flask equipped with a reflux device, 100 mg of 1-(3-bromo-4-methoxyphenyl)-2,3-dimethyl-4-(3,,4,5-trimethoxy Phenyl)-1,4-butanedione (7) dissolved in 2mlCH 2 Cl 2 In the solution, and add 2ml HCl methanol solution (made by adding 5ml concentrated hydrochloric acid to 100ml methanol solution). After the reaction mixture was heated to reflux for 1 hour, TLC detected that the reaction was complete. Crystals separated out after cooling, filtered to obtain 85 mg of white crystals, which were determined to be 2-(3-bromo-4-methoxyphenyl)-3,4-dimethyl-5-(3,,4,5- Trimethoxyphenyl) furan, the yield was 88.5%.

[0120] 1 HNMR(CDCl 3 )δppm 2.17~2.22(m, 6H, -CH 3 ), 3.86~3.91(m, 12H, OCH 3 ), 6.84-7.83 (m, 5H, ArH).

Embodiment 3

[0122]Preparation of 2-(3-bromo-4-methoxyphenyl)-3,4-dimethyl-5-(3,,4,5-trimethoxyphenyl)-1H-pyrrole (10).

[0123] Add 55 mg of 1-(3-bromo-4-methoxyphenyl)-2,3-dimethyl-4-(3,,4,5-trimethoxyphenyl)-1,4-butanedione (7) Dissolve in 0.7ml EtOH and 1ml CHCl 3 In the solution, heat and reflux for 10 hours. After cooling the reaction solution, the solvent was removed under reduced pressure to obtain a crude product, which was separated by silica gel column (ethyl acetate / petroleum ether = 1 / 4) to obtain a white solid, which was determined to be 2-(3-bromo-4-methoxybenzene) Yl)-5-(3,4,5-trimethoxyphenyl)-3,4-dimethylpyrrole, the yield was 75.8%.

[0124] 1 HNMR(DMSO)δppm 2.05(s, 3H, -CH 3 ), 2.11(s, 3H, -CH 3 ), 3.65(s, 3H, -OCH 3 ), 3.80(s, 6H, OCH 3 ), 3.84(s, 3H, OCH 3 ), 6.74-7.66 (m, 5H, ArH), 10.59 (s, 1H, -NH).

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Abstract

The invention discloses a dialkyl and diaryl tetrasubstituted heterocyclic compound, their preparing process and use, the compound has the general formula disclosed in the specification, wherein X is selected from S, O, NH and N-alkyl derivative, R1, R5, R'1, R'4, R'5 are selected from H, R6, R'5 are selected from alkyl, in particular alkyl of C1-C4, R2 is selected from H, methoxyl, R3 is selected from halogen, alkoxy, in particular alkyl of C1-C4 and PhCH2-alkoxy, R4 is selected from H, methoxyl, halogen, R'2 is selected from H, methoxyl, halogen and amine derivative, R'3 is selected from halogen, alkoxy, in particular alkyl of C1-C4 and PhCH2-alkoxy. The substituted heterocyclic compound can be used in preparing medicinal compositions, especially medicament for antineoplastic and anti-inflammatory actions.

Description

Technical field [0001] The invention relates to a tetra-substituted heterocyclic compound, a preparation method and application thereof, in particular to a dialkyl and diaryl tetra-substituted heterocyclic compound, a preparation method and application thereof. Background technique [0002] Cancer is one of the main diseases that seriously affect human health and threaten human life. In a broad sense, cancer refers to all malignant tumors. Its distinctive feature is that tumor cells have the ability to grow autonomously, continue to differentiate and proliferate, infiltrate and spread from the original site to other sites, and metastasize to other sites; further invade vital organs and cause failure , Which eventually led to death. According to WHO statistics, 6.9 million people die of malignant tumors globally every year, and 8.7 million new cases are diagnosed, and the number is increasing year by year. Therefore, countries all over the world are actively engaged in the researc...

Claims

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Application Information

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IPC IPC(8): A61K31/34A61K31/381A61K31/40A61P35/00C07D207/32C07D307/38C07D333/06
Inventor 赵康郑秀芳石继仙胡清萍
Owner TIANJIN UNIV
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