Browsing by Author "Prasad, Karnam Jayarampillai Rajendra"

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    Experimental and theoretical physicochemical study of a new dispirocompound: 4′-(4-fluorophenyl)-2′,7-dimethyl-1,4-dihydro-3H-dispiro[cyclopent[b]indol-2,5′-[1,2]oxazinan-6′3"-indolin]-2",3-dione
    (2021) Satheeshkumar, Rajendran; Montecinos, Rodrigo; Vera, Ariesny; Prasad, Karnam Jayarampillai Rajendra; Kaminsky, Werner; Salas, Cristian O.
    We present Et3N mediated synthesis of a novel dispirocompound from 5-methyl-2-(4'-fluorophenylidine)-1-oxo-1,2,3,8-tetrahydrocyclopent[b]indole, isatin, and sarcosine through 1,3-dipolar cycloaddition reaction. The crystal structure of synthesised compound, 4'-(4-fluorophenyl)-2',7-dimethyl-1,4-dihydro-3H-dispiro[cyclopent[b]indol-2,5'-[1,2]oxazinan-6',3 ''-indolinl-2 '',3-dione is reported. FT-IR, H-1 and C-13 NMR chemical shifts as measured and calculated using B3LYP method with the 6-311G(d,p) basis set in gas phase were found in good agreement. The optimized geometry of the dispirocompound was compared with experimental XRD values. DFT calculations of the molecular electrostatic potential (MEP), Non-covalent interactions and Hirshfeld Surface analysis, Non-linear optical (NLO) properties and frontier molecular orbitals (FMO) identified chemically active sites of the dispirocompound responsible for its chemical reactivity. (C) 2020 Elsevier B.V. All rights reserved.
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    Solvent-Free Synthesis of New Quinoline Derivatives via Eaton's Reagent Catalysed Friedlander Synthesis
    (2022) Satheeshkumar, Rajendran; Prasad, Karnam Jayarampillai Rajendra; Wang Wen-Long; Espinosa-Bustos, Christian; Salas, Cristian O.
    An interest for the development of new 2-acetyl/propanoyl quinolines via Friedlander synthesis is one of the most studied synthetic approaches. Herein we report the use of a freshly prepared Eaton's reagent (phosphorus pentoxide in methanesulfonic acid) as catalyst without solvents to obtain quinoline derivatives. Eleven 2-acetylquinolines were synthesized in high yields (85-96%) from symmetrical 1,2-diketone, butan-2,3-dione with o-aminoarylketones in the presence of Eaton's reagent. Subsequently, a novel regioselective solvent free reaction is reported for synthesis of o-aminoarylketones with unsymmetrical 1,2-diketone, pentan-2,3-dione, to yield different 2-propanoylquinolines. Eaton's reagent performs a unique way of this reaction as a powerful desiccant, condensing, cyclizing and dehydrating agent. Among these advantages of Eaton's reagent was found as an inexpensive and easily accessible catalyst for the Friedlander synthesis.
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    Synthesis of Novel Quin[1,2-b]Acridines: In Vitro Cytotoxicity and Molecular Docking Studies
    (2021) Satheeshkumar, Rajendran; Edatt, Lincy; Muthusankar, Aathi; Kumar, V. B. Sameer; Prasad, Karnam Jayarampillai Rajendra
    An attempted synthesis of 5-aryl-6,7-dihydrodibenzo[b,j][1,10]phenanthroline derivatives from 2,3-dihydroacridin-4(1H)-ones with 2-aminocarboxylic acid derivatives in presence of phosphorus oxychloride at 130C yielded a novel class of quin[1,2-b]acridine derivatives. The newly synthesized compounds showed a better cytotoxic activity against HeLa and MCF-7 cell lines during the structure-activity relationship (SAR) studies. To discover with the interactions of these molecules, we carried out molecular docking studies using the human protein kinase CK2 inhibitors. The molecular interaction results provided a number of elegant information for the outlook design of more potent inhibitors.