128508-22-5Relevant academic research and scientific papers
Reaction of (dimethylvinylidene)carbene with indole-3-carbaldehyde and its application in the synthesis of β-(dehydroprenyl)indole-based natural products
Sheu, Jyh-Horng,Chen, Chun-An,Chen, Buo-Horng
, p. 203 - 204 (2007/10/03)
Reaction of (dimethylvinylidene)carbene with indole-3-carbaldehyde gives various dehydroprenyl-based indoles. Efficient synthesis of the indole natural products yuehchukene and murrapanine, using this reaction as a key step, is also described.
Further study on the transformation of β-(1-hydroxybut-3-enyl)-indoles into 1-β-(indolyl)buta-1,3-diene, yuehchukene, murrapanine and analogues
Sheu, Jyh-Horng,Chen, Yua-Kuang,Chung, Huey-Fen,Lin, Song-Fang,Sung, Ping-Jyun
, p. 1959 - 1965 (2007/10/03)
β-(1-Hydroxybut-3-enyl)indoles have been converted into three indole natural products: yuehchukene 1, β-(dehydroprenyl)indole 2, murrapanine 3 and other analogues in a one step procedure under various acid-catalysed reaction conditions in THF. A one-pot synthesis of bisnoryuehchukene 15 starting from indole-3-carboxaldehyde was also achieved using a similar approach. β-(1-Hydroxybut-3-enyl)indoles are presumed to be dehydrated to 1-(β-indolyl)buta-1,3-dienes which then react further to give yuehchukene, murrapanine and other derivatives via a Diels-Alder pathway. The yields of 3 and normurrapanine 31 could be improved by using an aerial oxidation method. Murrapanine and analogues were found to exhibit potent cytotoxicity towards various cancer cell lines.
Synthesis of yuehchukene analogues, murrapanine and normurrapanine utilizing thermal reaction of β-(1-hydroxybutenyl)indoles under neutral reaction conditions
Sheu, Jyh-Horng,Chen, Yua-Kuang,Chung, Huey-Fen,Sung, Ping-Jyun,Lin, Song-Fong
, p. 1751 - 1758 (2007/10/03)
β-(1-Hydroxybutenyl)indoles, which were prepared in high yields from indole-3-carboxaldehyde, could be converted into yuehchukene analogues (8a, b), murrapanine(9a)and normurrapanine(9b)m one step under thermal-induced reaction conditions in neutral solution of ethylene glycol and water. β-(1-Hydroxybutenyl)indoles are supposed to be dehydrated to 1-(β-indolyl)-1,3-butadienes which react further to yuehchukene analogues via a Diels-Alder pathway. Murrapanine and normurrapanine showed a cytotoxicity toward KB cells.
STRUCTURE AND SYNTHESIS OF MURRAPANINE, A NOVEL SKELETAL INDOLE-NAPHTHOQUINONE ALKALOID AND CYTOTOXIC PRINCIPAL FROM MURRAYA PANICULATA VAR. OMPHALOCARPA
Wu, Tian-Shung,Liou, Meei-Jen,Lee, Chwan-Jen,Jong, Ting-Ting,McPhail, Andrew T.,et al.
, p. 6649 - 6652 (2007/10/02)
A novel skeletal cytotoxic indole-naphthoquinone alkaloid, murrapanine, has been isolated from the root bark of Murraya paniculata var. omphalocarpa and its structure has been established from spectral data and single-crystal X-ray analysis; the synthesis of murrapanine from indole-3-aldehyde is also described.
