73097-51-5Relevant academic research and scientific papers
Design, synthesis, anticancer activity, molecular docking and ADME studies of novel methylsulfonyl indole-benzimidazoles in comparison with ethylsulfonyl counterparts
Karadayi, Fikriye Zengin,Yaman, Murat,Kisla, Mehmet Murat,Konu, Ozlen,Ates-Alagoz, Zeynep
, p. 9010 - 9019 (2021/06/06)
Cancer poses a world-wide healthcare problem, demanding selective and effective therapy protocols. To address that, a vast amount of therapeutic candidates are being investigated in the field of medicinal chemistry. Accordingly, indole-benzimidazole structures have recently gained considerable interest because of their anticancer properties and estrogen receptor (ER) modulatory actions. In this study, novel methylsulfonyl indole-benzimidazole derivatives have been synthesized upon substitution of respectively the first (R1) and fifth (R2) positions of benzimidazole and indole groups. Structure and activity relationships were then studied via1H NMR, 13C NMR, mass spectral and in silico docking analyses, as well as cell viability measurements. We found that the compounds exhibited substantial affinity levels towards ER alpha (ERα). In addition, the correlation analysis of cytotoxicity profiles between ethyl- and methyl-sulfonyl indole-benzimidazoles revealed a collection of effective and consistent R1 and R2 substitutions. However, for some candidate derivatives, distinctive cytotoxicity levels and varying viability versus ERα affinity correlations were observable across the studies, suggesting that the sulfonyl side chain modifications themselves can also influence the ERα binding levels. These results demonstrated that our novel methylsulfonyl indole-benzimidazole derivatives, similar to their ethylsulfonyl counterparts, exhibit anticancer effects with potential estrogen receptor modulatory actions. This journal is
C2-Selective Branched Alkylation of Benzimidazoles by Rhodium(I)-Catalyzed C-H Activation
Tran, Ga?l,Confair, Danielle,Hesp, Kevin D.,Mascitti, Vincent,Ellman, Jonathan A.
, p. 9243 - 9252 (2017/09/11)
Herein, we report a Rh(I)/bisphosphine/K3PO4 catalytic system allowing for the first time the selective branched C-H alkylation of benzimidazoles with Michael acceptors. Branched alkylation with N,N-dimethyl acrylamide was successfully applied to the alkylation of a broad range of benzimidazoles incorporating a variety of N-substituents and with both electron-rich and -poor functionality displayed at different sites of the arene. Moreover, the introduction of a quaternary carbon was achieved by alkylation with ethyl methacrylate. The method was also shown to be applicable to the C2-selective branched alkylation of azabenzimidazoles.
Substituted Fused Imidazole Derivatives, Pharmaceutical Compositions, and Methods of Use Thereof
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Page/Page column 146, (2011/09/14)
Substituted fused imidazole derivatives, methods of their preparation, pharmaceutical compositions comprising a substituted fused imidazole derivative, and methods of use in treating inflammation are provided. The substituted fused imidazole derivatives may control the activity or the amount or both the activity and the amount of heme-oxygenase.
