20127-62-2Relevant academic research and scientific papers
Selective construction of alkaloid scaffolds by alcohol-based direct and mild aerobic oxidative Pictet-Spengler reactions
Han, Feng,Li, Huan,Liu, Haicheng,Liu, Jianping,Xu, Qing
supporting information, p. 7079 - 7085 (2020/10/02)
Employing TBN/TEMPO as the catalysts and oxygen as the oxidant, the biologically and pharmaceutically significant tetrahydro-β-carboline and β-carboline alkaloid scaffolds that used to be obtained by multi-step processes can now be selectively obtained in only one-stepviadirect aerobic oxidative Pictet-Spengler reactions of tryptamines with alcohols under mild conditions, with water generated as the byproduct. In this reaction, TBN/TEMPO was interestingly found to be able to facilitate the cyclization step of the whole reaction. This method tolerates a variety ofC- andN-substituted tryptamines, and both the more reactive benzylic and allylic alcohols and the less reactive aliphatic alcohols. This method can also be extended to dihydro-β-carboline synthesis and applied to the more available and more economical tryptophan for β-carboline synthesis, revealing its broad substrate scope and potential in synthetic applications.
Green synthesis method for beta-carboline heterocyclic compounds
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Paragraph 0084; 0085; 0086; 0087, (2018/09/11)
The invention discloses a green synthesis method for beta-carboline heterocyclic compounds. The green synthesis method includes that the beta-carboline heterocyclic compounds are made of alcohols compounds, oxidative condensation, cyclization and re-oxidation one-pot cascade reaction is carried out on tryptamines compounds and alcohol in oxygen under the catalytic effects of catalysts TEMPO and catalysts TBN to obtain the beta-carboline heterocyclic compounds, the reaction temperatures range from 40 DEG C to 120 DEG C, and the reaction time ranges from 6 hours to 48 hours. The green synthesismethod has the advantages that inexpensive, easily available, stable and low-toxicity alcohols which can come from wide sources are used as the raw materials for the beta-carboline heterocyclic compounds, the aerobic oxidative condensation, cyclization and re-oxidation cascade reaction is carried out on the tryptamines compounds and the alcohol under the synergistic catalytic effects of the catalysts TEMPO and the catalysts TBN and acetic acid solvent conditions to prepare the beta-carboline heterocyclic compounds, target products are high in selectivity, a byproduct is water, and accordinglythe green synthesis method is high in efficiency and free of pollution.
Synthesis and cytotoxic activities of 1-benzylidine substituted β-carboline derivatives
Cao, Rihui,Yi, Wei,Wu, Qifeng,Guan, Xiangdong,Feng, Manxiu,Ma, Chunming,Chen, Zhiyong,Song, Huacan,Peng, Wenlie
experimental part, p. 6558 - 6561 (2009/09/06)
A series of new β-carboline derivatives, bearing a benzylidine substituent at position-1, has been prepared and evaluated in vitro against a panel of human cell lines. The N2-benzylated β-carbolinium bromates represented the most interesting cytotoxic activities. In particular, compounds 19 were found to be the most potent compounds with IC50 values lower than 5 μM against 10 strains human tumor cell lines. These results confirmed that the N2-benzyl substituent on the β-carboline ring played an important role in the modulation of the cytotoxic activities and suggested that further development of such compounds may be interest.
