33032-83-6Relevant articles and documents
Synthesis of homotaurine and 1-substituted homotaurines from α,β-unsaturated nitriles
Ma, Yunhai,Xu, Jiaxi
supporting information; experimental part, p. 2225 - 2230 (2012/09/22)
Homotaurine and a series of 1-substituted homotaurines were readily synthesized in satisfactory to good yields via the Michael addition of thioacetic acid to aliphatic and aromatic α,β-unsaturated nitriles followed by lithium aluminum hydride mediated reduction and performic acid oxidation. The synthesis of 1,1-disubstituted homotaurines was attempted with β,β-disubstituted acrylonitriles as starting materials but failed due to steric hindrance. The current process is an efficient method for the synthesis of 1-substituted homotaurines. Georg Thieme Verlag Stuttgart New York.
OH-/silica-mediated one-pot synthesis of dithiocarbamates under solvent-free conditions
Bardajee, Ghasem Rezanejade,Afsari, Hamid Samareh,Sadraei, Seyediraj,Taimoory, Seyedehmaryamdokht
experimental part, p. 871 - 878 (2012/07/31)
An efficient, versatile, and environmentally benign method for the synthesis of dithiocarbamates under solvent-free conditions is reported. The Michael addition of electron-deficient alkenes with alkyl or aryl amines and CS2 in the presence of OH-/silica in a one-pot three-component reaction protocol gave the corresponding dithiocarbamates in good to excellent yields. This method is suitable for a wide range of amines and a variety of Michael acceptors in solvent-free conditions. The results of the present work show the desired products in excellent yields. Copyright Taylor and Francis Group, LLC 2012.
Exploring the structural requirements for inhibition of the ubiquitin E3 ligase breast cancer associated protein 2 (BCA2) as a treatment for breast cancer
Brahemi, Ghali,Kona, Fathima R.,Fiasella, Annalisa,Buac, Daniela,Soukupová, Jitka,Brancale, Andrea,Burger, Angelika M.,Westwell, Andrew D.
supporting information; experimental part, p. 2757 - 2765 (2010/08/20)
The zinc-ejecting aldehyde dehydrogenase (ALDH) inhibitory drug disulfiram (DSF) was found to be a breast cancer-associated protein 2 (BCA2) inhibitor with potent antitumor activity. We herein describe our work in the synthesis and evaluation of new series of zinc-affinic molecules to explore the structural requirements for selective BCA2-inhibitory antitumor activity. An N(C - S)S - S motif was found to be required, based on selective activity in BCA2-expressing breast cancer cell lines and against recombinant BCA2 protein. Notably, the DSF analogs (3a and 3c) and dithio(peroxo)thioate compounds (5d and 5f) were found to have potent activity (submicromolar IC50) in BCA2 positive MCF-7 and T47D cells but were inactive (IC50 > 10 μM) in BCA2 negative MDA-MB-231 breast cancer cells and the normal breast epithelial cell line MCF10A. Testing in the isogenic BCA2 +ve MDA-MB-231/ER cell line restored antitumor activity for compounds that were inactive in the BCA2 -ve MDA-MB-231 cell line. In contrast, structurally related dithiocarbamates and benzisothiazolones (lacking the disulfide bond) were all inactive. Compounds 5d and 5f were additionally found to lack ALDH-inhibitory activity, suggestive of selective E3 ligase-inhibitory activity and worthy of further development.
