25488-33-9Relevant academic research and scientific papers
Divergent synthesis of prenylated carbazole alkaloid (+)-S-mahanimbine led to the discovery of a notch activator
Yedukondalu, Nalli,Gupta, Gourav,Nadkarni, Janhavi R.,Gupta, Vivek Kumar,Syed, Sajad Hussain,Ali, Asif
, p. 83069 - 83077 (2016)
(+)-Mahanimbine (1), a prenylated carbazole alkaloid, was isolated from the stems of Murraya koenigii. Herein we developed a divergent synthesis by the Vilsmeier-Haack reaction, which involves unusual oxidative cyclization and transformation to several distinct tetracyclic carbazole natural products (2-9). The new chemical entities were identified by extensive 1D and 2D NMR data, HR-ESI-MS, and comparison with the known literature. Compounds 2 and 5 were further characterized by X-ray crystal analysis. Compounds (1-9) were screened against the notch pathway activation in which the new compound 8 exhibited prominent notch activation in a reporter gene assay with an EC50 value equal to 0.85 μM. It also inhibited the cell proliferation and colony formation of the K562 human leukemia cell line.
A simple BF3?Et2O-mediated cycloaddition reaction to the formation of cyclic monoterpenoid pyrano[3,2-a]carbazole alkaloids
Tan, Siow-Ping,Nafiah, Mohd Azlan
, p. 395 - 399 (2021/09/07)
A Lewis acid BF3?Et2O-mediated intramolecular cycloaddition reaction of mahanimbine (1) is described. Three cycloadducts, bicyclomahanimbine (2), cyclomahanimbine (3) and murrayazolinine (4) were obtained. The structural characterization of these compounds was determined by 1D and 2D NMR experiments. These compounds showed no cytotoxic activity against human MRC-5 cells (IC50 > 60 μg/mL). Compound 3 showed the highest inhibition cytotoxic effects against HeLa and HL-60 cancer cells with IC50 values of 10.0 and 28.7 μg/mL, respectively. This strategy opens a new approach for the synthesis of biologically significant cyclic monoterpenoid pyrano[3,2-a]carbazole alkaloids.
