Site‐Selective Rhodium(III)‐Catalyzed C−H Amination of 7‐Azaindoles with Anthranils: Synthesis and Anticancer Evaluation

Abstract

The site‐selective C−H amination reaction of 7‐azaindoles with various benzisoxazoles as amination surrogates under cationic rhodium(III) catalysis is described. This transformation efficiently provides a range of ortho‐aminated N‐aryl‐7‐azaindoles with excellent site‐selectivity and functional group compatibility. The formed ortho‐aminated 7‐azaindoles were readily transformed into biologically relevant heterocycles such as azaindoloacridine, azaindoloacridone, and bis‐indole compounds. Moreover, the synthetic derivatives were tested for in vitro anticancer activity against human breast adenocarcinoma cells (MCF‐7), human renal carcinoma cells (786‐O), and human prostate adenocarcinoma cells (DU145). Notably, some synthetic compounds were found to display most potent anticancer activity, compared to that of anticancer doxorubicin as a positive control.

Synthesis of TMPA Derivatives through Sequential Ir(III)-Catalyzed C–H Alkylation and Their Antidiabetic Evaluation

“… 9 Particularly, Meldrum’s diazo compounds were also utilized as a new class of α-diazo agents to afford the corresponding alkylated and/or cyclized adducts. 10 In continuation of our recent studies on the biologically active compounds based on catalytic C–H functionalization, 11 we herein disclose the iridium(III)-catalyzed α-alkylation of acetophenones with alcohols followed by the ketone-directed Ir(III)- and Rh(III)-catalyzed ortho -C–H alkylation of acetophenones with Meldrum’s diazo esters. As a result, this protocol may be beneficial to guide the design of a variety of antidiabetic TMPA derivatives and represents a catalytic alternative to transcend the barriers imposed by a previous multistep synthetic approach.…”

Analysis of alkaloids (indole alkaloids, isoquinoline alkaloids, tropane alkaloids)

“…Plant secondary metabolites are a diverse range of biologically active molecules having multiple pharmacological actions like antimicrobial, stimulant, analgesic, anthelmintic, anticoagulant, antiacne, and antioxidant, among others (Debnath et al, 2012;Bhakta, 2012, 2013;Dey et al, 2012bDey et al, , 2014Karuna et al, 2018aKaruna et al, , 2018bKundu et al, 2019). Different synthetic compounds show potential biological activity in vitro as well as in vivo ( Jeon et al, 2017;Jeong et al, 2017a, b;Kim et al, 2018;Lee et al, 2018Lee et al, , 2019Richa et al, 2019;Tae et al, 2018), and various formulations of existing drugs are also developed to increase the safety profile (Gorain et al, 2014;Karmakar et al, 2015;Maity et al, 2016). In spite of this technological development, humans from almost every culture are efficiently employing the plant-derived compounds for the anticipation and management of multiple health disorders for many centuries (Dey et al, 2012a, c).…”

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“…Traditional healers use their knowledge to cure or treat different diseases with the help of medicinal plants [13][14][15]. Based on their ethnomedicinal properties, one can accelerate design and development of rational drugs or plant-derived physiologically active molecules after being fused with synthetic chemistry, QSAR and nanotechnology to combat various deadly diseases like diabetes and cancer [16][17][18][19][20].…”