918659-56-0Relevant articles and documents
Synthesis and bioactivity studies of covalent inhibitors derived from (-)-Chaetominine
Chen, Deheng,Feng, Xuexin,Lyu, Xilin,Wang, Dachi,Wang, Huan,Wu, Gaoxing,Yan, Ziqin,Yang, Jin-Ming,Zhao, Yujun,Zhou, Xian
, (2021)
We reported herein the synthesis and bioactivity studies of compounds derived from the natural product (-)-Chaetominine (6). The key feature of these compounds is the incorporation of electrophilic groups that are capable of forming covalent bonds with the cysteine or threonine residues of cellular proteins. The cell growth inhibition activities of these derivatives of 6 were tested in four cancer cell lines, i.e. a leukemia cell line K562, a multiple myeloma cell line MM1.S, an acute myeloid leukemia cell line MV4-11, and a colon cancer cell line RKO. The data show that cellular growth inhibition IC50 values of 29, an acrylamide-containing molecule, are 9-17 folds more potent than that of 6, while other acrylamide-containing compounds are much less potent, suggesting 29 might have covalent interactions with cellular target proteins. Collectively, incorporation of an acrylamide moiety into 6 is a good strategy to improve its cell growth inhibition activity in cancer cell lines.
Biomimetic synthesis of (-)-chaetominine epimers via copper-catalyzed radical cyclization
Deng, Xu,Liang, Kangjiang,Tong, Xiaogang,Ding, Ming,Li, Dashan,Xia, Chengfeng
, p. 3699 - 3704 (2015/05/20)
Synthetic endeavors toward (-)-chaetominine via copper-catalyzed radical cyclization are reported. Both of the pyrido[2,3,b]-indole ring (C ring) and imidazolidinone (D ring) are efficiently constructed in one-pot manner. It's unveiled that the newly form
Complexity generation by chemical synthesis: A five-step synthesis of (-)-chaetominine from l-tryptophan and its biosynthetic implications
Xu, Chu-Pei,Luo, Shi-Peng,Wang, Ai-E,Huang, Pei-Qiang
supporting information, p. 2859 - 2863 (2014/05/06)
We demonstrated, for the first time, that on the basis of chemistry principles, the hexacyclic peptidyl alkaloid (-)-chaetominine (1) can be synthesized in a straightforward manner from l-Trp. The approach features the efficient generation of molecular complexity via a tandem C3/C14 syn-selective epoxidation (dr = 3:2)-annulative ring-opening reaction and a regioselective epimerization at C14. The successful production of (-)-chaetominine (1) from l-Trp could be helpful for revealing how the configuration of l-tryptophan becomes inverted in the biosynthetic pathway of (-)-chaetominine (1). This journal is the Partner Organisations 2014.