272449-67-9Relevant articles and documents
A simple route for the synthesis of novel norcantharimide derivatives via acidolysis with hydrochloric acid(gas)
K?se, Aytekin
, p. 1171 - 1178 (2021/03/08)
In this work, seven new norcantharimide derivatives were synthesized by an acidolysis method. The compounds were prepared by acidolyzing trans-1,4-diacetate and trans-1,2-chloroacetate structures, which were obtained by stereospecific cleavage of the internal etheric bond of the tricyclic imides. The HCl(gas) was produced from the reaction of H2SO4 with NaCl. The resulting gas was bubbled into the reaction mixture. Trans-1,4-diacetate and trans-1,2-chloroacetate were thus acidolyzed, and the corresponding diol and halohydrin products were obtained respectively in moderate overall yields from low-cost starting materials, using simple and easily scalable chemistry. The products were characterized by means of spectroscopic techniques. The synthesized compounds have high potential as anticancer agents and can be valuable for studies in this area.
Design of aromatic-containing cell-penetrating peptide mimics with structurally modified π electronics
DeRonde, Brittany M.,Birke, Alexander,Tew, Gregory N.
supporting information, p. 3013 - 3019 (2015/02/05)
Cell-penetrating peptides (CPPs) and their synthetic mimics (CPPMs) represent a class of molecules that facilitate the intracellular delivery of various cargo. Previous studies indicated that the presence of aromatic functionalities improved CPPM activity. Given that aromatic functionalities play prominent roles in membrane biology and participate in various π interactions, we explored whether these interactions could be optimized for improved CPPM activity. CPPMs were synthesized by ring-opening metathesis polymerization by using monomers that contained aromatic rings substituted with electron-donating and electron-withdrawing groups and covered an electrostatic potential range from -29.69 to + 15.57 kcalmol-1. These groups altered the quadrupole moments of the aromatic systems and were used to test if such structural modifications changed CPPM activity. CPPMs were added to dye-loaded vesicles and the release of carboxyfluorescein was monitored as a function of polymer concentration. Changes in the effective polymer concentration to release 50% of the dye (effective concentration, EC50) were monitored. Results from this assay showed that the strength of the electron-donating and electron-withdrawing groups incorporated in the CPPMs did not alter polymer EC50 values or activity. This suggests that other design parameters may have a stronger impact on CPPM activity. In addition, these results indicate that a wide range of aromatic groups can be incorporated without negatively impacting polymer activity.
Synthesis and characterization of novel bi- and tricyclic α-amino acids
Johnson, Matthew R.,Gauuan, Jolicia F.,Guo, Cheng,Guzzo, Peter R.,Le, Van-Duc,Shenoy, Rajesh A.,Hamby, James,Roark, Howard,Stier, Michael,Mangette, John E.
, p. 2769 - 2793 (2011/08/22)
As part of a medicinal chemistry collaboration, a number of novel bi- and tricyclic aamino acids were prepared through various routes and characterized by 1 H nuclearOverhauser effect difference experiments. The syntheses provide a number of routes to access some highly substituted amino acid derivatives that have not been reported previously. It is envisaged that the chemistry described here could be applied to the synthesis of other unique substrates Taylor & Francis Group, LLC.
