150258-59-6Relevant academic research and scientific papers
Synthesis and biological activity of optically active phenylbutenoid dimers
Chu, Jeonghyun,Suh, Dong Hoon,Lee, Gehyung,Han, Ah-Reum,Chae, Song Wha,Lee, Hwa Jeong,Seo, Eun-Kyoung,Lim, Hee-Jong
supporting information; experimental part, p. 1817 - 1821 (2011/10/17)
The total synthesis of optically active phenylbutenoid dimers 1, 3, and ent-3 is described. The key step to access optically active cyclohexene rings was achieved by Diels-Alder reaction of chiral acryloyloxazolinone 9 and phenylbetadiene 10.
Non-Amine Based Analogues of Lavendustin A as Protein-Tyrosine Kinase Inhibitors
Smyth, Mark S.,Stefanova, Irena,Hartmann, Frank,Horak, Ivan D.,Osherov, Nir,et al.
, p. 3010 - 3014 (2007/10/02)
The fermentation product lavendustin A (1) is a protein-tyrosine kinase (PTK) inhibitor whose active pharmacophore has previously been shown to reside in the more simplified salicyl-containing benzylamine 2.Amine 2 bears some structural resemblance to two other natural product PTK inhibitors, erbstatin (3) and piceatannol (4).Non-amine containing analogues of 2 were therefore synthesized which incorporated additional aspects of either erbstatin or piceatannol.Examination of these inhibitors in immunoprecipitated p56lck, epidermal growth factor receptor (EGFR), and c-erb B-2/HER 2/neu PTK preparation showed that compound 12 (IC50=60 nM)was one of the most potent p56lek inhibitors reported to date.These results demonstrate that nitrogen is not an essential component of the lavendustin A pharmacophore 2 and that 1,2-diarylethanes and ethenes bearing a salicyl moiety appear to be valuable structural motifs for the constuction of extremely potent PTK inhibitors.
