91985-75-0Relevant academic research and scientific papers
Structure-activity relationship in the antitumor activity of 6-, 8- or 6,8-substituted 3-benzylamino-β-carboline derivatives
Ikeda, Reiko,Kimura, Takanori,Tsutsumi, Tatsuya,Tamura, Syunsuke,Sakai, Norio,Konakahara, Takeo
, p. 3506 - 3515 (2012/07/03)
We synthesized 47 kinds of 3-amino- or 3-benzylamino-β-carboline derivatives with a substituent on the 6-, 8-, or 6,8-carbon atoms and evaluated their antitumor activities for Hela S-3 and Sarcoma 180 cell lines using a 3-(4,5-dimethylthiazol-2-yl)-2,5-di
3-Benzylamino-β-carboline derivatives induce apoptosis through G 2/M arrest in human carcinoma cells HeLa S-3
Ikeda, Reiko,Iwaki, Toshie,Iida, Tomoko,Okabayashi, Takasumi,Nishi, Eishiro,Kurosawa, Masaki,Sakai, Norio,Konakahara, Takeo
experimental part, p. 636 - 646 (2011/03/20)
β-Carboline derivatives are known as the lead compounds for anti-tumor agents. To examine an optimal structure for anti-tumor activity, we synthesized a variety of β-carboline derivatives, possessing a variety of substituents on the nitrogen atom of the amino group of 3-amino-β-carboline, and evaluated their anti-tumor activity for HeLa S-3 cell line. 3-(4,5- Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay showed that an optimal structure for anti-tumor activity was 3-cyclohexylmethylamino (1e) or 3-benzylamino-β-carboline (1f). An optimal counter anion of 2-methyl-3-benzylamino- β-carbolinium salts was a triflate anion 2c. In addition, the introduction of a hydroxyl group on the meta-position of the benzyl group of 3-benzylamino-β-carboline (3e) enhanced its anti-tumor activity. Hoechst 33342 staining and DNA fragmentation assay suggested that 1f, 2c and 3e induced cell death by apoptosis unlike 1e. Flow cytometry analysis showed that 1f, 2c and 3e induced cell apoptosis through arrest of the cell cycle in the G2/M phase.
3-Amino-β-carboline derivatives and the benzodiazepine receptor. Synthesis of a selective antagonist of the sedative action of diazepam
Dodd,Ouannes,Prado de Carvalho,Valin,Venault,Chapouthier,Rossier,Potier
, p. 824 - 828 (2007/10/02)
Seven 3-N-substituted derivatives of 3-amino-β-carboline were synthesized and their affinities for the benzodiazepine receptor were assessed in vitro. Two compounds, 3-(ethylamino)-β-carboline and 3-[(methoxycarbonyl)amino]-β-carboline (β-CMC), showing IC50 values of 460 and 71 nM, respectively, were selected for in vivo studies. The former compound showed long-lasting proconvulsant activity in Papio papio baboons while β-CMC was shown in mice to selectively antagonize the sedative effects of diazepam without exhibiting convulsant, proconvulsant, or anxiogenic activity by itself.
