362014-09-3Relevant academic research and scientific papers
Development of the β-lactam type molecular scaffold for selective estrogen receptor α modulator action: synthesis and cytotoxic effects in MCF-7 breast cancer cells
Carr, Miriam,Knox, Andrew J. S.,Lloyd, David G.,Zisterer, Daniela M.,Meegan, Mary J.
, p. 117 - 130 (2016)
The estrogen receptors (ERα and ERβ) which are ligand inducible nuclear receptors are recognized as pharmaceutical targets for diseases such as osteoporosis and breast cancer. There is an increasing interest in the discovery of subtype Selective Estrogen Receptor Modulators (SERMs). A series of novel β-lactam compounds with estrogen receptor modulator properties have been synthesized. The antiproliferative effects of these compounds on human MCF-7 breast tumor cells are reported, together with binding affinity for the ERα and ERβ receptors. The most potent compound 15g demonstrated antiproliferative effects on MCF-7 breast tumor cells (IC50=186 nM) and ERα binding (IC50=4.3 nM) with 75-fold ERα/β receptor binding selectivity. The effect of positioning of the characteristic amine containing substituted aryl ring (on C-4 or N-1 of the β-lactam scaffold) on the antiproliferative activity and ER-binding properties of the β-lactam compounds is rationalized in a molecular modeling study.
Development of the carboxamide protecting group, 4-(tert -butyldimethylsiloxy)-2-methoxybenzyl
Muranaka, Kazuhiro,Ichikawa, Satoshi,Matsuda, Akira
, p. 9278 - 9293 (2012/01/04)
The new carboxamide protecting group, 4-(tert-butyldimethylsiloxy)-2- methoxybenzyl (SiMB), has been developed. While this SiMB group can be removed using mild basic desilylation methods, it can also be deprotected under strongly acidic or oxidative conditions. An application of this group to simple carboxamide groups, as well as to more complex and acid-sensitive adenosine derivatives containing a cyclophane scaffold, was also demonstrated.
