Purrocoline derivative and synthetic method and application thereof

A synthesis method and compound technology, which can be used in pharmaceutical combinations, medical preparations containing active ingredients, pharmaceutical formulations, etc., can solve the problems of large chemical pollution, increase reaction consumption, etc., and achieve simplified operation, good activity, and reduced chemical pollution. Effect

Inactive Publication Date: 2014-03-19
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the prior art, many methods for obtaining indolizine derivatives by artificial synthesis are disclosed, such as publication numbers CN1373130A, CN103087061A, CN1948310A and other patents all disclosing the synthetic methods of indolizine compounds, but in these existing synthetic methods Both need to react in the presence of a solvent, which increases the consumption of the reaction on the one hand, and on the other hand has a large chemical pollution problem

Method used

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  • Purrocoline derivative and synthetic method and application thereof
  • Purrocoline derivative and synthetic method and application thereof
  • Purrocoline derivative and synthetic method and application thereof

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Embodiment 1

[0025] Embodiment 1: the preparation of 2-benzyl-3-phenyl indolizine

[0026] 0.3 mmol (62.4 mg) of 1,3-diphenyl-prop-2-yn-1-ol and 1.5 mmol (139.5 mg) of 2-picoline were added to the flask, followed by 1,3-diphenyl- Prop-2-yn-1-ol was reacted with 20 mol% (30 mg) of samarium trifluoromethanesulfonate catalyst at 120°C and stirred until complete (TLC followed the reaction, about 24 hours). After the reaction is complete, cool to room temperature, pour the reactant into 10-30mL of water, and add 20-30mL of ethyl acetate for extraction, collect the extract phase, wash with saturated brine (10-20mL) three times, and then wash with anhydrous Na 2 SO 4 Dry, filter, remove the solvent from the filtrate under reduced pressure, and purify the residue by silica gel column chromatography, eluting with an eluent composed of ethyl acetate and petroleum ether with a volume ratio of 1:20, and evaporate the eluent under reduced pressure solvent to obtain 76.4 mg of green oily liquid 1a.

...

Embodiment 2

[0031] Embodiment 2: Preparation of 2-benzyl-1-methyl-3-phenylindolizine

[0032] 0.3 mmol (62.4 mg) of 1,3-diphenyl-prop-2-yn-1-ol and 1.5 mmol (160 mg) of 2-ethylpyridine were added to the flask, followed by 1,3-diphenyl-prop-2-yn-1-ol -2-Alkyn-1-ol was reacted with 20 mol% (30 mg) of samarium trifluoromethanesulfonate as a catalyst at 120°C until complete (TLC followed the reaction, about 24 hours). After the reaction is complete, cool to room temperature, pour the reactant into 10-30 mL of water, extract with 20-30 mL of ethyl acetate, collect the extract phase, wash with saturated brine (10-20 mL) three times, and finally wash with anhydrous Na 2 SO 4 Dry, filter, remove the solvent from the filtrate under reduced pressure, and purify the residue by silica gel column chromatography, eluting with an eluent composed of ethyl acetate and petroleum ether with a volume ratio of 1:20, and evaporate the eluent under reduced pressure solvent to obtain 80.2 mg of green oily liqu...

Embodiment 3

[0037] Embodiment 3: Preparation of 2-benzyl-3-phenylindolizine-1-carboxylate ethyl ester

[0038]0.3 mmol (62.4 mg) of 1,3-diphenyl-prop-2-yn-1-ol and 1.5 mmol (247.5 mg) of 2-acetoxyethylpyridine were added to the flask, followed by 1,3-diphenyl 20 mol% (30 mg) of samarium trifluoromethanesulfonate catalyst was used in the base-prop-2-yn-1-ol, and the reaction was stirred at 120°C until complete (TLC followed the reaction, about 24h). After the reaction is complete, cool to room temperature, pour the reactant into 10-30mL of water, and extract with 20-30mL of ethyl acetate, collect the extract phase, wash with saturated brine (10-20mL) three times, and finally wash with anhydrous Na 2 SO 4 Dry, filter, remove the solvent from the filtrate under reduced pressure, and purify the residue by silica gel column chromatography, eluting with an eluent composed of ethyl acetate and petroleum ether with a volume ratio of 1:20, and evaporate the eluent under reduced pressure solvent ...

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Abstract

The invention discloses a purrocoline derivative and a synthetic method and application thereof. The purrocoline derivative with a novel structure can be prepared by reacting propargyl alcohol and a 2-alkyl pyridine compound by taking samarium trifluoromethanesulfonate as a catalyst under the condition without a solvent; the reaction consumption and the chemical contamination are reduced, the cost is reduced and the operation is simplified; the obtained purrocoline derivative has better activity on a gastric cancer cell strain MGC80-3. The structural formula of the purrocoline derivative is shown in a formula (I) in the specification, wherein R<1> is phenyl, 4-methoxyphenyl, 4-fluorophenyl and 2-chlorphenyl or thienyl, R<2> is phenyl, and R<3> is H, phenyl, methyl, a nitrile group or an ethyl acetate group.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a series of indolizine derivatives and their synthesis methods and applications. Background technique [0002] Malignant tumor is one of the major diseases that seriously threaten human health. Every year, 11 million people are diagnosed with cancer worldwide. It has become the second leading cause of death after cardiovascular and cerebrovascular diseases. At present, in the method of treating cancer, chemical drug therapy is a research field with the fastest development. Among them, natural indolizine compounds are known for their anti-virus, anti-tumor, anti-inflammatory, anti-fungal, anti-Leishmania, Various biological activities such as anti-oxidation, histamine H3 receptor antagonism and immune regulation have attracted more and more attention from researchers. However, due to its low natural content and difficulty in separation and purification, it has brought ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/437A61P35/00
CPCC07D471/04
Inventor 潘英明
Owner GUANGXI NORMAL UNIV
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