58617-31-5

Upstream product

• 110-00-9 furan 
• 930-88-1 N-methylmaleimide 
• 74-83-9 methyl bromide 
• 6253-28-7 exo-7-oxabicyclo[2.2.1]hept-4-ene-2,3-dicarboximide 
• 6118-51-0 exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride 
• 74-89-5 methylamine 
• 155793-97-8 endo,endo-2,3-dibromo-7-oxanorborneno<2,3-c>succinimide 

Downstream Products

• 96-48-0 4-butanolide 

Relevant academic research and scientific papers

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.

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.

POTENTIALLY ANTICARCINOGENIC NOVEL ISOINDOLE-1,3-DIONE DERIVATIVES AND SYNTHESIS METHOD FOR SUCH COMPOUNDS

The invention is related to novel isoindole-1,3-dione derivatives which are determined to be effective in vitro on certain cancer types (e.g., Lung, breast and cervical cancer) as well as the synthesis method of such compounds for use in the chemistry sector, pharmaceuticals industry and pharmacy sector.

Synthesis and anticancer activity evaluation of new isoindole analogues

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 in the presence of a catalytic amount of H2SO4 in order to yield new isoindole derivatives (8a and 8b). The anticancer activity of these compounds was evaluated against MCF-7 (breast adenocarcinoma) and A549 (adenocarcinomic human alveolar basal epithelial) cell lines. The synthesized compounds showed concentration- and time-dependent inhibitory effects on the viability of both cell lines. Compound 8a was more toxic compared to 8b in both cancer cell lines, having higher cytotoxicity against A549 cells. Testing the toxicity properties of these compounds on the BEAS 2B (human bronchial epithelial) cell line indicated that while both compounds decreased the cell viability of cancer cells, they were less toxic on healthy lung cells. Microscopy images of A549 cells after treatment with the new isoindole derivatives displayed characteristic apoptotic morphology compared to BEAS 2B cells. The results demonstrated here suggest that these new compounds might be considered as possible potential anticancer agents for the treatment of lung and breast cancer.

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

Self-activation in de novo designed mimics of cell-penetrating peptides

DIY transduction: Cell-penetrating peptides (CPPs) efficiently cross the nonpolar biological membrane, but activation by hydrophobic counterions is essential for transport activity. Polymeric mimics of CPPs are coupled with hydrophobic side chains; the "self-activation" in these species is demonstrated by transport of the fluorescent probe CF out of bilayer vesicles. Copyright

1,3-dipolar cycloaddition reactions of N-methyl-substituted tricyclic imides

The [3+2]?cycloadditions of N-methyl derivatives of unsaturated imides with various nitrile oxides to yield new bridged isoxazoline derivatives with potential biological activity is described.

ANTIMICROBIAL POLYMERS

The invention generally relates to novel polymers (SMAMPs) and their syntheses and use. The polymers exhibit promising properties of AMPs. In particularly, for example, a ring-opening metathesis polymerization (ROMP) platform was developed that allows syntheses of SMAMPs that employ a minimum number of norbornene-based building blocks and/or enable easy and independent variation of hydrophobic and hydrophilic groups in the monomer units and/or along the polymeric backbone to finetune and select desirable properties of the polymers.

Reductive heck reactions of N-methyl-substituted tricyclic imides

The palladium-catalyzed hydroarylation of N-methyl-substituted tricyclic imides was studied in order to find a new stereoselective access to a series of new exoaryl(hetaryl)-substituted tricyclic N-methylimides.

Comparison of facially amphiphilic versus segregated monomers in the design of antibacterial copolymers

A direct comparison of two strategies for designing antimicrobial polymers is presented. Previously, we published several reports on the use of facially amphiphilic (FA) monomers which led to polynorbornenes with excellent antimicrobial activities and sel