17872-55-8Relevant articles and documents
Self-interrupted synthesis of sterically hindered aliphatic polyamide dendrimers
Jishkariani, Davit,MacDermaid, Christopher M.,Timsina, Yam N.,Grama, Silvia,Gillani, Syeda S.,Divar, Masoumeh,Yadavalli, Srujana S.,Moussodia, Ralph-Olivier,Leowanawat, Pawaret,Camacho, Angely M. Berrios,Walter, Ricardo,Goulian, Mark,Klein, Michael L.,Percec, Virgil
, p. E2275 - E2284 (2017)
2,2-Bis(azidomethyl)propionic acid was prepared in four steps and 85% yield from the commercially available 2,2-bis(hydroxymethyl) propionic acid and used as the starting building block for the divergent, convergent, and double-stage convergent-divergent iterative methods for the synthesis of dendrimers and dendrons containing ethylenediamine (EDA), piperazine (PPZ), and methyl 2,2- bis(aminomethyl)propionate (COOMe) cores. These cores have the same multiplicity but different conformations. A diversity of synthetic methods were used for the synthesis of dendrimers and dendrons. Regardless of the method used, a self-interruption of the synthesis was observed at generation 4 for the dendrimer with an EDA core and at generation 5 for the one with a PPZ core, whereas for the COOMe core, self-interruption was observed at generation 6 dendron, which is equivalent to generation 5 dendrimer. Molecular modeling and molecular-dynamics simulations demonstrated that the observed self-interruption is determined by the backfolding of the azide groups at the periphery of the dendrimer. The latter conformation inhibits completely the heterogeneous hydrogenation of the azide groups catalyzed by 10% Pd/carbon as well as homogeneous hydrogenation by the Staudinger method. These self-terminated polyamide dendrimers are enzymatically and hydrolytically stable and also exhibit antimicrobial activity. Thus, these nanoscale constructs open avenues for biomedical applications.
Norbornadienes: Robust and Scalable Building Blocks for Cascade "click" Coupling of High Molecular Weight Polymers
St Amant, Andre H.,Discekici, Emre H.,Bailey, Sophia J.,Zayas, Manuel S.,Song, Jung-Ah,Shankel, Shelby L.,Nguyen, Shay N.,Bates, Morgan W.,Anastasaki, Athina,Hawker, Craig J.,De Alaniz, Javier Read
supporting information, p. 13619 - 13624 (2019/09/10)
Herein, we report the development of a scalable and synthetically robust building block based on norbornadiene (NBD) that can be broadly incorporated into a variety of macromolecular architectures using traditional living polymerization techniques. By tak
Studies toward novel peptidomimetic inhibitors of thioredoxin-thioredoxin reductase system
K?ossowski, Szymon,Muchowicz, Angelika,Firczuk, Ma?gorzata,?wiech, Marta,Redzej, Adam,Golab, Jakub,Ostaszewski, Ryszard
supporting information; experimental part, p. 55 - 67 (2012/02/15)
Thioredoxins (Trx) are ubiquitous multifunctional low-molecular weight proteins that together with thioredoxin reductases (TrxR) participate in the maintenance of protein thiol homeostasis in NADPH-dependent reactions. An increasing number of data reveal that the Trx-TrxR system is an attractive target for anticancer therapies. In this work, we have elaborated a new and simple synthetic approach employing Ugi reaction to synthesize several new inhibitors of this system. The influence of various electrophilic fragments of this new class of compounds on the inhibition of the Trx-TrxR system was evaluated. As a result, a new compound 19a (SK053), which inhibits the activity of the Trx-TrxR system and exhibits antitumor activity, was obtained. Biologic analyses revealed that 19a inhibits induction of NF-κB and AP-1 and decreases H2O2 scavenging capacity in tumor cells. Altogether, we show that 19a is a novel potential antitumor peptidomimetic inhibitor that can be used as a starting compound for further optimization.
