94258-44-3Relevant academic research and scientific papers
Synthesis and biological evaluation of novel N9-heterobivalent β-carbolines as angiogenesis inhibitors
Guo, Liang,Ma, Qin,Chen, Wei,Fan, Wenxi,Zhang, Jie,Dai, Bin
, p. 375 - 387 (2019/01/10)
A series of novel N9-heterobivalent β-carbolines has been synthesized. All the novel compounds were tested for their anticancer activity against six tumour cell lines in vitro. Among these molecules, compounds 5b, and 5w exhibited strong cytotoxic activities with IC50 value of lower than 20 μM. Acute toxicities and antitumor efficacies of the selected compounds in mice were also evaluated, compounds 5b and 5w exhibited that tumour inhibition rate of over 40% in the Sarcoma 180 and Lewis lung cancer animal models. Preliminary structure–activity relationships (SARs) analysis indicated that: (1) C1-methylation and C7-methoxylation were favorable for increased activities; (2) 3-Pyridyl or 2-thienyl group substituent into position-1 of the β-carboline core, and the aryl substituent into another β-carboline ring might be detrimental to cytotoxic effects of this class compounds. Investigation of the preliminary mechanism of action demonstrated that compound 5b had obvious angiogenesis inhibitory effects in the chicken chorioallantoic membrane (CAM) assay.
Synthesis and structure-activity relationships of asymmetric dimeric β-carboline derivatives as potential antitumor agents
Guo, Liang,Chen, Wei,Cao, Rihui,Fan, Wenxi,Ma, Qin,Zhang, Jie,Dai, Bin
, p. 253 - 265 (2018/02/15)
A series of newly asymmetric dimeric β-carbolines with a spacer of 4–6 methylene units between the indole nitrogen and the harmine oxygen were synthesized. Structures of all the novel synthesized compounds were confirmed by their spectral and analytical studies. All of the synthesized compounds were screened for their in vitro cytotoxic activity against nine cancer cell lines. The results revealed that compounds 7c, 7o and 7s exhibited the highest cytotoxic activities with IC50 values of less than 20 μM against the tumor cell lines tested. Acute toxicities and antitumor efficacies of the selected compounds in mice were also evaluated, and compound 7o exhibited potent antitumor activities with the tumor inhibition rate of over 40%. The wound healing assay displayed a specific impairment in the motility of the HT-29 cells, which suggested the anti-metastatic potential of compound 7o. Moreover, compound 7o had obvious angiogenesis inhibitory effects in the chicken chorioallantoic membrane (CAM) assay. Preliminary structure-activity relationship (SAR) analysis indicated that: (1) 3-phenylpropyl substituent at the N9-position of the indole ring was the most suitable group giving rise to potent cytotoxic agents; (2) the spacer length affected the antitumor potencies, and four methylene units were more favorable.
Cu-catalyzed mild and efficient oxidation of THβCs using air: Application in practical total syntheses of perlolyrine and flazin
Zheng, Bo,Trieu, Tien Ha,Meng, Tian-Zhuo,Lu, Xia,Dong, Jing,Zhang, Qiang,Shi, Xiao-Xin
, p. 6834 - 6839 (2018/02/23)
A mild, efficient and environmentally benign method for synthesis of aromatic β-carbolines via Cu(ii)-catalyzed oxidation of 1,2,3,4-tetrahydro-β-carbolines (THβCs) was developed, in which air (O2) was used as the clean oxidant. This method has advantages such as environmentally friendliness, mildness, very good tolerance of functional groups, high yielding and easy experiment operation. In addition, this new methodology was successfully applied in the efficient and practical total syntheses of β-carboline alkaloids perlolyrine and flazin.
Efficient and practical one-pot conversions of n- tosyltetrahydroisoquinolines into isoquinolines and of N-tosyltetrahydro-β- carbolines into β-carbolines through tandem β-elimination and aromatization
Dong, Jing,Shi, Xiao-Xin,Yan, Jing-Jing,Xing, Jing,Zhang, Qiang,Xiao, Sen
experimental part, p. 6987 - 6992 (2011/02/24)
An efficient, practical, and general method for conversions of N-tosyltetrahydroisoquinolines (N-tosyl-THIQs) into isoquinolines and of N-tosyltetrahydro-β-carbolines (N-tosyl-THBCs) into β-carbolines is described. Treatment of N-tosyl-THIQs or N-tosyl-THBCs with base in dimethyl sulfoxide afforded dihydroisoquinolines or dihydro-β-carbolines as intermediates, and these were then oxidized in situ by molecular oxygen to furnish isoquinolines or β-carbolines in good to high yields. Both one-pot conversions occurred through tandem β-elimination and aromatization. An efficient method for conversions ofN-tosyltetrahydroisoquinolines (N-tosyl-THIQs) and N-tosyltetrahydro-β-carbolines (N-tosyl-THBCs) into isoquinolines and β-carbolines is described. Treatment ofN-tosyl-THIQs or N-tosyl-THBCs with base affords dihydroisoquinolines or dihydro-β- carbolines. These can be oxidized in situ by molecular oxygen to furnish isoquinolines or β-carbolines. Copyright
A mild and efficient route to 2-benzyl tryptamine derivatives via ring-opening of β-carbolines
Hadjaz, Fariza,Yous, Sa?d,Lebegue, Nicolas,Berthelot, Pascal,Carato, Pascal
experimental part, p. 10004 - 10008 (2009/04/03)
We described a mild and easy method, in two steps, by which various benzyl groups were introduced in the C-2 position of tryptamine. The first step consisted on the synthesis of β-carbolines, starting from tryptamine derivatives, by a Pictet-Spengler reaction. Ring-opening of the β-carbolines, by hydrogenation, led to the desired 2-substituted benzyl tryptamine indole products. A supplementary step of alkylation could be realized to give N-alkyl-2-substituted benzyl tryptamine. During these reactions, nitrogen atoms require no step of protection.
