Study On Tandem Reaction Via Propargyl Alcohol And Bioactivities Of ?-carbolines

Objective:Using propargyl alcohol as a substrate,under the guidance of the green chemical concept,a variety of biologically active fused ring compounds,such as?-carboline com-pounds,dehydro-?-lapachone,bicyclodimedione dihydrofuran and 7H-benzo[c]fluoren are constructed using inexpensive,environmentally friendly,and atom-economically compatible methods.Then test the universality of its construction method.At the same time,14 kinds of?-carboline compounds were tested for their biological activity,and the?-carboline compounds were studied for biological activity and the effects of different substituents on their biological activities were investigated.Methods:?1?A series cyclization reaction with other active substances was carried out using propargyl alcohol as a substrate.?2?According to the literature,the range of reaction conditions,such as the type of catalyst,the type of solvent,the amount of catalyst and the temperature,are initially de-lineated,and then the optimal conditions for the reaction are screened out through experi-ments.?3?The reaction was carried out under optimal conditions.The influence of different material was tested by changing the substituents on the raw materials,and the universality of the synthesis method was verified.?4?To test the biological activity of the?-carboline compound,the cell proliferation was examined by culturing the gastric cancer cell HGC-27 using the CCK-8 method.Results:?1?Using FeCl3·6H2O as a catalyst to catalyze the synthesis of?-carboline com-pounds by the propargyl alcohol and?E?-1-methyl-1H-indole-2-carbaldehyde oxime under the mild conditions.?2?Meyer-Schuster rearrangement of propargyl alcohol was carried out under mild conditions using zinc triflate?Zn?OTf?₂?catalyst,and tandem cyclization reaction with2-hydroxy-1,4-naphthoquinone was carried out.One-pot method forms a series of dehy-dro-?-lapachone structures.?3?Using 2-hydroxy-1,4-naphthoquinone and propargyl alcohol as substrates and FeCl₃ as catalyst,a series of complicated bicyclodimedione dihydrofuran compounds were synthesized in high yield.In this reaction,two molecules of propargyl alcohol undergo Meyer-Schuster rearrangement,and tandem cyclization,Diels-Alder reaction and intra-molecular electron transfer.?4?Introduces a new method for the synthesis of the 7H-benzo[c]fluorene?BcF?skeleton.The method uses Sc?OTf?₃ as a catalyst with the help of oxidant2,5-dihydroxy-1,4-benzoquinone.The propargyl alcohol undergoes its own tandem cy-clization reaction to synthesize the 7H-benzo[c]fluorene?BcF?skeleton structure.?5?Through bioactivity experiments,five?-carboline compounds were screened for the statistical significance of the survival rate of gastric cancer cells HGC-27.Conclusion:?1?In this paper,propargyl alcohol was used as substrate to react with different active structures,such as?-carboline,dehydro-?-lapachone,bicyclodimedione dihydrofuran and7H-benzo[c]fluorine?BcF?were synthesized respectively.There are four categories of a total of 45 new fused ring compounds.?2?The biological activity of?-carboline was briefly explored by the CCK-8 method.