41300-23-6Relevant articles and documents
Synthesis of bivalent ligands of β-carboline-3-carboxylates via a palladium-catalyzed homocoupling process
Yin, Wenyuan,Sarma, P. V. V. Srirama,Ma, Jun,Han, Dongmei,Chen, Jessica L.,Cook, James M.
, p. 6363 - 6368 (2005)
The first synthesis of bivalent ligands of β-carboline-3-carboxylates has been achieved from β-carboline-3-carboxylate tert-butyl ester (βCCt) via Sonogashira and palladium-catalyzed homocoupling processes. The Boc protected intermediate, an iodo-β-carboline-3-carboxylate, was employed to provide a general entry into a series of bivalent ligands structurally similar to βCCt.
β-Carbolines as benzodiazepine receptor ligands. 1. Synthesis and benzodiazepine receptor interaction of esters of β-carboline-3-carboxylic acid
Lippke,Schunack,Wenning,Muller
, p. 499 - 503 (1983)
Several esters of β-carboline-3-carboxylic acid were synthesized and tested in respect to their affinity for the benzodiazepine receptor in bovine cortex membranes. Out of these derivatives, the methyl, ethyl, and n-propyl ester were clearly the most pote
Molecular hybrid design, synthesis, in vitro and in vivo anticancer evaluation, and mechanism of action of N-acylhydrazone linked, heterobivalent β-carbolines
Chen, Wei,Chen, Xiaofei,Dai, Bin,Fan, Wenxi,Guo, Liang,Ma, Qin,Zhang, Jie
, (2020/02/05)
A series of N-acylhydrazone-linked, heterobivalent β-carboline derivatives was designed and synthesized from L-tryptophan in a nine-step reaction sequence. The effort resulted in the heterobivalent β-carbolines 10a–t in good yields. The target compounds were characterized by 1H NMR, 13C NMR and high-resolution mass spectrometry (HRMS). The in vitro cytotoxic activity of the synthesized compounds was evaluated against normal EA.HY926 cells and five cancer cell lines: LLC (Lewis lung carcinoma), BGC-823 (gastric carcinoma), CT-26 (murine colon carcinoma), Bel-7402 (liver carcinoma), and MCF-7 (breast carcinoma). Compound 10e, with an IC50 value of 2.41 μM against EA.HY926 cells, was the most potent inhibitor. It showed cytotoxicity against all five cancer cell lines of different origin – murine and human, with IC50 values ranging from 4.2 ± 0.7 to 18.5 ± 3.1 μM. A study of structure-activity relationships indicated that the influence on cytotoxic activities of the substituent in the R9′-position followed the tendency, 2,3,4,5,6-perfluorophenylmethyl > 4-fluorobenzyl > 3-phenylpropyl group. The antitumor efficacies of the selected compounds were also evaluated in mice. Compound 10e exhibited potent antitumor activity, with tumor inhibition of more than 40% for Sarcoma 180 and 36.7% for Lewis lung cancer. Furthermore, the pharmacological mechanisms showed that compound 10e has a certain impairment in the motility of LLC cells, which suggests the anti-metastatic potential. And compound 10e inhibited angiogenesis in chicken chorioallantoic membrane assay, and the anti-angiogenetic potency was more potent than the reference drug combretastatin A4-phosphate (CA4P) at a concentration 50 μM.
Design, synthesis, and anti-proliferative evaluation of 1: H -1,2,3-triazole grafted tetrahydro-β-carboline-chalcone/ferrocenylchalcone conjugates in estrogen responsive and triple negative breast cancer cells
Awolade, Paul,Cele, Nosipho,Gu, Liang,Kaur, Mandeep,Kumar, Vipan,Pillay, Ruvesh Pascal,Sharma, Bharvi,Singh, Parvesh
, p. 11137 - 11147 (2020/07/15)
A series of 1H-1,2,3 triazole grafted tetrahydro-β-carboline-chalcone/ferrocenylchalcone conjugates were synthesized and in vitro evaluated against estrogen responsive (MCF-7) and triple negative (MDA-MB-231) breast cancer cells. Comparative analysis reve
Pd/C-Catalyzed Dehydrogenative [3+2] Cycloaddition for the Synthesis of Functionalized Tropanes
Wang, Hai-Jun,Guo, Lei,Zhu, Cheng-Feng,Luo, Yun-Fei,Li, You-Gui,Wu, Xiang
supporting information, p. 5456 - 5459 (2018/10/20)
A Pd/C-catalyzed cascade approach for the synthesis of attractive benzo-fused tropanes was developed. The reaction proceeds through a sequential Pd/C-catalyzed dehydrogenative formation of azomethine ylides from amines and 1,3-dipolar cycloaddition. It allows the generation of structurally complex benzo-fused tropanes in good yields with excellent diastereoselectivities under mild reaction conditions. Preliminary results of asymmetric version of the reaction reveal that the copper catalyst and chiral monophosphoramidite ligand can furnish optically active products with moderate ee.
