Department Of Chemistry

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Subject: search.filters.subject.Indole

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    Chitosan-supported FeCl3 catalyzed multicomponent synthesis of tetrahydroisoquinoline-indole hybrids with promising activity against chloroquine resistant Plasmodium falciparum
    (Elsevier B.V., 2022-10-26T00:00:00) Kaur, Pavneet; Sharma, Priyanka; Kumar, Vinod; Sahal, Dinkar; Kumar, Rakesh
    An operationally simple three-component coupling of tetrahydroisoquinoline (THIQ), aldehydes and indoles or indole-3-carboxylic acids has been achieved using chitosan-ionic liquid supported FeCl3 (chit-IL@FeCl3) as a recyclable heterogeneous catalyst. The developed waste-free approach provided rapid access to biologically important THIQ-indole hybrids without the use of any additive or ligand. The synthesized THIQ-indole hybrids were evaluated as antiplasmodial agents against chloroquine-sensitive (Pf3D7) and chloroquine-resistant (PfINDO) strains of Plasmodium falciparum. Compounds 4b (most potent against Pf3D7) and 4g (most potent against PfINDO) showed IC50 values of 1.32 and 0.26 �g/mL respectively. Also, 4g showed strong cytocidal action against both rings and trophozoite stages. Furthermore, cytotoxic study against human liver HUH 7 cells revealed that the most potent compound 4g with an excellent resistance index of 0.07 is also relatively non-toxic. The results of this study suggest that THIQ-indole hybrids hold an enormous potential for developing new antimalarial agents with novel mechanism of action. � 2022 Elsevier B.V.
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    Recent advances for construction and late-stage diversification of indole core via C-H bond activation/functionalization
    (Elsevier, 2021-02-26T00:00:00) Sinha, Arun Kumar; Kumar, Rakesh
    Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials. Owing to such a huge potential, continuous efforts are being put forward to construct or diversify this scaffold. This chapter provides an overview of various recently developed methodologies for the construction of indole core via C-H bond activation/functionalization. In particular, Pd- and Ru-mediated cyclization strategies involving Csp2-H functionalization of monofunctionalized arene substrates with the unsaturated bond of alkene and alkyne are highlighted herein. Also, late-stage diversification of indole system (C4-C7 position) via direct C-H activation is covered. Furthermore, the mechanistic aspects of some of these reactions are discussed as well. � 2021 Elsevier Inc. All rights reserved.