272449-67-9

Upstream product

• 100-39-0 benzyl bromide 
• 6253-28-7 exo-7-oxabicyclo[2.2.1]hept-4-ene-2,3-dicarboximide 
• 110-00-9 furan 
• 1631-26-1 1-benzyl-1H-pyrrole-2,5-dione 
• 6118-51-0 exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride 
• 100-46-9 benzylamine 
• 100-51-6 benzyl alcohol 
• 29745-04-8 norcantharidin 

Downstream Products

• 730964-25-7 5,6-dihydroxy-exo-N-(phenylmethyl)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboximide 
• 73611-42-4 10-oxa-4-aza-tricyclo[5.2.1.0(2,6)]decane 
• 4938-65-2 C₁₅H₁₉NO 
• 913331-06-3 C₅₆H₆₂N₆O₁₂SSi 
• 913331-04-1 C₅₉H₆₀N₆O₁₁SSi 
• 913331-05-2 C₅₈H₆₀N₄O₁₂SSi 
• 913331-03-0 C₅₂H₅₇N₃O₁₂SSi 
• 1631-26-1 1-benzyl-1H-pyrrole-2,5-dione 

Relevant academic research and scientific papers

A simple route for the synthesis of novel norcantharimide derivatives via acidolysis with hydrochloric acid(gas)

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.

Synthesis and biological evaluation of new chloro/acetoxy substituted isoindole analogues as new tyrosine kinase inhibitors

We have developed a versatile synthetic approach for the synthesis of new isoindole derivatives via the cleavage of ethers from tricyclic imide skeleton compounds. An exo-cycloadduct prepared from the Diels–Alder reaction of furan and maleic anhydride furnished imide derivatives. The epoxide ring was opened with Ac2O or Ac2O/AcCl in the presence of a catalytic amount of H2SO4 in order to yield new isoindole derivatives 8a-d and 9a-d. The anticancer activity of these compounds was evaluated against the HeLa cell lines. The synthesized compounds showed inhibitory effects on the viability of HeLa cells and the degree of cytotoxicity was increased with the level of bigger branched isoindole derivatives. To better understand the acting mechanism of these molecules, western blot analysis was performed with using mTOR and its downstream substrates. In addition, human mTOR and ribozomal S6 kinase β1 (RS6Kβ1) have been investigated with molecular modelling studies as possible targets for compound series 8 and 9.

Design of aromatic-containing cell-penetrating peptide mimics with structurally modified π electronics

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.

Enantioselective access to bicyclo[4.2.0]octanes by a sequence of [2+2] photocycloaddition/reduction/fragmentation

Tricks of the trade: Because intramolecular Cu-catalyzed access to bicyclo[4.2.0]octanes is not feasible, an oxygen bridge was introduced to facilitate the [2+2] photocycloaddition. Starting from compounds similar to 1, products such as 2 could be obtaine

Synthesis and characterization of novel bi- and tricyclic α-amino acids

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.

cis-tetrahydrofuran-3,4-diol structure as a key skeleton of new protecting groups removable by self-cyclization under oxidative conditions

(Chemical Equation Presented) A variety of carbonate-type acyl groups having a cis-tetrahydrofuran-3,4-diol (1,4-anhydroerythritol) backbone structure and a TrS or MMTrS group have been examined as new "protected" protecting groups of the 5′-hydroxyl grou

Synthesis on N-alkylated maleimides

A two step synthesis of N-alkylated maleimides is presented. This method allows for the use of widely available starting materials and produces maleimides in high purity and yields. The maleimide precursors are of interest for potential thermo- and photo-setting polymerization processes.