18866-73-4Relevant articles and documents
Highly reactive, liquid diacrylamides via synergistic combination of spatially arranged curing moieties
Maier, Maximilian,Schmidt, Magnus S.,Ringwald, Markus,Fik, Christoph P.
, p. 372 - 383 (2017)
Six polymerizable N,N′-diacylamides containing spatially arranged N-acryl, N-allyl and/or N-alkyl groups were prepared via two-step syntheses and characterized by 1H/13C NMR-spectra, refractive index (RI) and viscosity measurements. Photo DSC measurements on activated samples provided reactivity parameters ΔHp, Rp,max and tmax, while FTIR spectra before and after curing elucidated the underlying polymerization mechanism. Mechanical testing of the obtained polymers exhibited gradual differences in network densities, depending on the intramolecular arrangement and number of functional groups. Overall, a general building principle for highly reactive, liquid diacrylamides via synergistic combination of optimally arranged functional groups could be identified. The highest possible level of intramolecular synergism was found for low viscous N,N′-diacryloyl-N,N′-diallyl-1,4-but-2-enediamine.
The effect of vicinal difluorination on the conformation and potency of histone deacetylase inhibitors
Bhadbhade, Mohan,Daryl Ariawan, A.,Ho, Junming,Hunter, Luke,Mansour, Flora,Richardson, Nicole
supporting information, (2021/07/22)
Histone deacetylase enzymes (HDACs) are potential targets for the treatment of cancer and other diseases, but it is challenging to design isoform selective agents. In this work, we created new analogs of two established but non selective HDAC inhibitors. We decorated the central linker chains of the molecules with specifically positioned fluorine atoms in order to control the molecular conformations. The fluorinated analogs were screened against a panel of 11 HDAC isoforms, and minor differences in isoform selectivity patterns were observed.
Synthesis and Characterization of Cyanobutadiene Isomers-Molecules of Astrochemical Significance
Esselman, Brian J.,Hyland, Grace E.,Knezz, Stephanie N.,Kougias, Samuel M.,Lee, Daniel J.,McMahon, Robert J.,Owen, Andrew N.,Patel, Aatmik R.,Sanchez, Rodrigo A.,Woods, R. Claude
, (2020/05/05)
Four cyanobutadiene isomers of considerable interest to the organic chemistry, molecular spectroscopy, and astrochemistry communities were synthesized in good yields and isolated as pure compounds: (E)-1-cyano-1,3-butadiene (E-1), (Z)-1-cyano-1,3-butadiene (Z-1), 4-cyano-1,2-butadiene (2), and 2-cyano-1,3-butadiene (3). A diastereoselective synthesis was developed to generate (E)-1-cyano-1,3-butadiene (1) (10:1 E/Z) via tandem SN2 and E2′ reactions. The potential energy surfaces of the E2′ reactions leading to (E)- A nd (Z)-1-cyano-1,3-butadiene (1) were analyzed by density functional theory calculations, and the observed diastereoselectivity was rationalized in the context of the Curtin-Hammett principle. The preparation of pure samples of these reactive compounds enables measurement of their laboratory rotational spectra, which are the critical data needed to search for these species in space by radioastronomy.
The Significance of Chirality in Drug Design and Synthesis of Bitopic Ligands as D3 Receptor (D3R) Selective Agonists
Battiti, Francisco O.,Cemaj, Sophie L.,Guerrero, Adrian M.,Shaik, Anver Basha,Lam, Jenny,Rais, Rana,Slusher, Barbara S.,Deschamps, Jeffery R.,Imler, Greg H.,Newman, Amy Hauck,Bonifazi, Alessandro
, p. 6287 - 6314 (2019/08/02)
Because of the large degree of homology among dopamine D2-like receptors, discovering ligands capable of discriminating between the D2, D3, and D4 receptor subtypes remains a significant challenge. Previous work has exemplified the use of bitopic ligands as a powerful strategy in achieving subtype selectivity for agonists and antagonists alike. Inspired by the potential for chemical modification of the D3 preferential agonists (+)-PD128,907 (1) and PF592,379 (2), we synthesized bitopic structures to further improve their D3R selectivity. We found that the (2S,5S) conformation of scaffold 2 resulted in a privileged architecture with increased affinity and selectivity for the D3R. In addition, a cyclopropyl moiety incorporated into the linker and full resolution of the chiral centers resulted in lead compound 53 and eutomer 53a that demonstrate significantly higher D3R binding selectivities than the reference compounds. Moreover, the favorable metabolic stability in rat liver microsomes supports future studies in in vivo models of dopamine system dysregulation.
