17952-82-8Relevant articles and documents
First total synthesis of the proposed structures of orisuaveolines A and B
Zhang, Jie,Da, Shijun,Feng, Xiaolin,Chen, Xiaoyi,Jiang, Jianhui,Li, Ying
, p. 123 - 126 (2013)
First total synthesis of the proposed structures of β- indoloquinazoline alkaloids orisuaveolines A and B is reported. The key steps of the synthesis included a Pictet-Spengler reaction to build a six-member lactam which further transformed into target molecular by a one-pot condensation. This synthesis provided an access to the proposed structures of orisuaveolines A and B in a short and convenient manner from inexpensive, commercially available starting materials. The structures of our synthesized products were confirmed by 2D-NMR experiments. First total synthesis of the proposed structures of β-indoloquinazoline alkaloids orisuaveolines A and B is reported. The key steps of the synthesis included a Pictet-Spengler reaction to build a six-member lactam which further transformed into target molecular by a one-pot condensation. The structures of our synthesized products were confirmed by 2D-NMR experiments. Copyright
Investigation into the stability and reactivity of the pentacyclic alkaloid dehydroevodiamine and the benz-analog thereof
Wehle, Sarah,Espargaró, Alba,Sabaté, Raimon,Decker, Michael
, p. 2535 - 2543 (2016/04/26)
Limited synthetic approaches to obtain the biologically active alkaloid dehydroevodiamine (DHED) are known to date. Undesired demethylation in the most widely applied route was found to be a hampering side reaction for the benz-DHED derivative leading to a quinazolinone, which represents a benz-rutaecarpine derivative. For rutaecarpine, a related plant alkaloid, many different synthetic approaches have been described. Alternative reaction procedures to obtain DHED such as methylation of rutaecarpine and oxidation of evodiamine were investigated to make DHED more easily accessible and the latter method proved to be the most successful one. Furthermore, the remarkable equilibrium between the ring closed quinazolinium and the ring open form of the compounds was systematically investigated by UV-vis measurements. The ring open form and the quinazolinium salt, form the same species when incubated in buffer solution for 24 h. A better soluble form, i.e., 'hydroxyevodiamine', seems to represent the biologically active form that has not yet been described.
Optical evodiamine derivatives: Asymmetric synthesis and antitumor activity
Li, Zhen-Gang,Dong, Guo-Qiang,Wang, Sheng-Zheng,Miao, Zhen-Yuan,Yao, Jian-Zhong,Zhang, Wan-Nian,Sheng, Chun-Quan
, p. 267 - 271 (2015/04/14)
Evodiamine and its derivatives have an asymmetric center at the C13b position. Herein, isomers of evodiamine derivatives 2 and 3 were obtained by straightforward asymmetric total synthesis. Their inhibitory activities toward topoisomerases I and II and th
Efficient synthesis of eudistomin U and evaluation of its cytotoxicity
Roggero, Chad M.,Giulietti, Jennifer M.,Mulcahy, Seann P.
supporting information, p. 3549 - 3551 (2015/02/19)
Eudistomin U is a member of a subclass of naturally occurring indole alkaloids known as β-carbolines. These molecules are reported to have diverse biological activity and high binding affinity to DNA, which make them attractive targets for total synthesis
