A solvent-promoted and -controlled regioselective bond alkylation reactions of para-quinone methides (p-QMs) with N-H free-indoline and 1,2,3,4-tetrahydroquinoline (THQ) under metal-free conditions have been developed. In the presence of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)...

The compounds reducing tumor cell viability and disrupting DNA topoisomerase reactions have been widely used in anticancer drug development. Ellipticine (5,carbazole) is a potent intercalating agent that interferes with nucleic acid processing through interaction with DNA topoisomerase II. Although ellipticine is a wellcharacterized compound, it is not a widely-accepted drug due to the adverse effects detected upon administration. We have previously reported two novel ellipticine derivatives, N-methyl-5-demethyl ellipticine (ET-1) and 2-methyl-N-methyl-5demethyl ellipticinium iodide (ET-2) as potent compounds targeting DNA topoisomerase II. This study covers an extended synthesis, characterization, and activity data for five new salts of N-methyl 5-demetyl ellipticine (Z-1, Z-2, Z-4, Z-5 and Z-6) having several organic halides and their effects on human topoisomerase II enzymes. Moreover, combined in silico studies were conducted for better understanding of modes of action of studied molecules at the binding pocket of target. Our results showed that three of the derivatives (Z-1, Z-2, and Z-6) have considerable effect on the catalytic activity of human topoisomerase II implying the influence of alkyl groups added to the parental structure of ellipticine.

A series of novel murrayaquinone a derivatives were synthesized and their anti‐cancer activity were evaluated on healthy colon cell lines (CCD‐18Co), primary (Caco‐2) and metastatic (DLD‐1) colon cancer cell lines. The results showed that the cytotoxicity of murrayaquinone molecules is significantly high even in micromolar levels. The DNA binding, cell cycle arrest and metabolic activity studies of these molecules were also carried out and the results showed that these molecules induce apoptosis. In conclusion, the data support further studies on murrayaquinone derivatives toward selection of a candidate for cancer treatment.

Indium-catalyzed, solvent-enabled regioselective C6-or N1-alkylations of 2,3-disubstituted indoles with para-quinone methides are developed under mild conditions. Notably, highly selective and switchable alkylations were selectively achieved by adjusting the reaction conditions. Moreover, scalability and further transformations of the alkylation products are demonstrated, and this operationally simple methodology is amenable to the late-stage C6-functionalization of the indomethacin drug. The reaction pathways were explained with the support of experimental and density functional theory studies.

Amides are important compounds in organic synthesis and have significant roles in pharmaceuticals, agrochemicals, and materials. The Ritter reaction is a classical transformation to amides between nitriles and alcohol derivatives or olefins. para‐Quinone methides (p‐QMs) are highly reactive intermediates in organic synthesis. The cover picture visualizes that, as new Ritter acceptors, para‐quinone methides are joining the alcohols and alkenes, known Ritter acceptors, driving to amides. More information can be found in the Research Article by Nurullah Saracoglu et al.

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1,6‐Conjugate addition/Ritter‐type amidation of para‐quinone methides (p‐QMs) with nitriles is described. This transformation is an environmentally friendly approach by the use of NaHSO4 as a low‐loading, inexpensive, green, and recyclable catalyst. Diarylmethane amides are afforded in excellent yields through a one‐pot process from p‐QMs and nitrile derivatives under mild reaction conditions.