32620-86-3Relevant articles and documents
Reductive heck reactions of N-methyl-substituted tricyclic imides
Goksu, Gokce,Ocal, Nuket,Kaufmann, Dieter E.
, p. 1302 - 1308 (2010)
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.
Substituent effects on the reversibility of furan - Maleimide cycloadditions
Boutelle, Robert C.,Northrop, Brian H.
, p. 7994 - 8002 (2011)
The effects of furan and maleimide substitution on the dynamic reversibility of their Diels - Alder reactivity have been investigated computationally and by 1H NMR spectroscopy. Furan and furan derivatives bearing methoxy, methyl, or formyl groups at their 2- or 3-positions were investigated with maleimide and maleimide derivatives bearing N-methyl, N-allyl, and N-phenyl substituents. Computational predictions indicate that electronic and regiochemical effects of furan substitution significantly influence their Diels - Alder reactivity with maleimide, with reaction free energies of exo adduct formation ranging from ΔG = - 9.4 to 0.9 kcal/mol and transition state barriers to exo adduct formation ranging from ΔG? = 18.9 to 25.6 kcal/mol. Much less variation was observed for the reactivity of N-substituted maleimide derivatives and furan, with reaction and transition state free energies each falling within a range of 1.1 kcal/mol. Dynamic exchange experiments monitored by 1H NMR spectroscopy support computational predictions. The results indicate the reactivity and reversibility of furan - maleimide cycloadditions can be tuned significantly through the addition of appropriate substituents and have implications in the use of furan and maleimide derivatives in the construction of thermally responsive organic materials.
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.
POTENTIALLY ANTICARCINOGENIC NOVEL ISOINDOLE-1,3-DIONE DERIVATIVES AND SYNTHESIS METHOD FOR SUCH COMPOUNDS
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Page/Page column 9; 10, (2019/11/12)
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
K?se, Aytekin,Bal, Y?ld?z,Kishal?, Nurhan H.,?anl?-Mohamed, Gül?ah,Kara, Yunus
, p. 779 - 786 (2017/03/06)
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.
