1197392-20-3Relevant articles and documents
Pyrano[3,2-a]carbazole alkaloids as effective agents against ischemic stroke in vitro and in vivo
Zang, Yingda,Song, Xiuyun,Li, Chuangjun,Ma, Jie,Chu, Shifeng,Liu, Dandan,Ren, Qian,Li, Yan,Chen, Naihong,Zhang, Dongming
, p. 438 - 448 (2018)
A series of pyrano[3,2-a]carbazole alkaloids were designed and synthesized as analogues of Claulansine F (Clau F, 10a) isolated from Clausena lansium. Some of compounds showed strong neuroprotective effects and were promising agents against ischemic stroke. Among these compounds, 7c was the most active in inhibiting the programmed death of PC12 cells and primary cortical neurons. This compound induced neuroprotection following ischemic reperfusion and decreased neurological deficit scores in treated animals. Furthermore, 7c could penetrate the blood-brain barrier (BBB) in rats, and its exposure in the brain was 4.3-fold higher than that in plasma. More importantly, compared to edaravone, 7c exhibited stronger free radical scavenging activity. Our findings suggest that 7c may be promising for further evaluation as an intervention for ischemic stroke.
Synthesis of the Pyrano[3,2- a ]carbazole Alkaloids Koenine, Koenimbine, Koenigine, Koenigicine, and Structural Reassignment of Mukonicine
Schuster, Christian,R?nnefahrt, Marika,Julich-Gruner, Konstanze K.,J?ger, Anne,Schmidt, Arndt W.,Kn?lker, Hans-Joachim
, p. 150 - 160 (2015/12/26)
Using the palladium(II)-catalyzed oxidative cyclization of a diarylamine and the annulation of a dimethylpyran ring by Lewis acid promoted reaction with prenal as key steps, the total syntheses of the 6-oxygenated pyrano[3,2-a]carbazole alkaloids koenine and koenimbine, and of the 6,7-dioxygenated pyrano[3,2-a]carbazole alkaloids koenigine and koenigicine (koenimbidine, koenidine) were achieved. Moreover, these studies led to an improved synthetic route to the 2,6-dioxygenated carbazole alkaloid glycozolidol. Mukonicine, originally published as 6,8-dimethoxypyrano[3,2-a]carbazole, was found to be identical with koenigicine.