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Öğe A Novel Methodology for the Asymmetric Synthesis of 2,3,5-Trisubstituted Piperazine Derivatives(Georg Thieme Verlag Kg, 2024) Beksultanova, Nurzhan; Ozdemir, Ozge; Cakir, Sidika Polat; Aygun, Muhittin; Dogan, OzdemirPiperazines constitute an important structural feature of many pharmaceuticals. For the discovery of new drugs, the ability to modify the lead compound's structure is crucial. Herein, we provide an efficient method for the synthesis of chiral 2,3,5-trisubstituted piperazine structures. Our route enables the synthesis of several novel chiral aryl aziridinyl ketones that could be converted into aziridine-fused bicyclic imines. The reduction of these imines and the nucleophilic ring-opening reaction of the aziridine ring allowed us to synthesize highly functionalized piperazine derivatives.Öğe Enantioselective synthesis of 2-aziridinyl phosphonates and studies of their biological activities(Amer Chemical Soc, 2016) Dogan, Ozdemir; Cakir, Sidika Polat; Beksultanova, Nurzhan; Altanlar, Nurten; Simsek, Duygu[Anstract Not Available]Öğe Enantioselective synthesis of new chiral 2-aziridinyl phosphonates and studies of their biological activities(Pergamon-Elsevier Science Ltd, 2017) Dogan, Ozdemir; Cakir, Sidika Polat; Beksultanova, Nurzhan; Altanlar, Nurten; Simsek, Duygu; Karabiyik, HasanA new series of chiral aziridinyl phosphonates has been synthesized and evaluated for antibacterial and antifungal activities. For the synthesis, a Gabriel-Cromwell reaction was used to form aziridinyl phosphonates in 52-83% yield. In order to evaluate antibacterial and antifungal activities, MIC values were measured. Although most of the compounds showed insignificant activity, two of them provided low to moderate antifungal activity. (C) 2017 Elsevier Ltd. All rights reserved.Öğe Synthesis of (3,6-dihydro-2H-pyran-2-yl)phosphonate derivatives and investigation of catalyst effect on frontier molecular orbitals using DFT method(Taylor & Francis Ltd, 2016) Hossain, Md Shakhawoat; Cakir, Sidika Polat; Ozpinar, Gul Altinbas; Nadeem, Said; Demir, Ayhan S.Hetero Diels-Alder (HDA) reactions between 2,3-dimethyl-1,3-butadiene and diethyl ester of aroyl phosphonates catalyzed by AlCl3 to afford (3,6-dihydro-2H-pyran-2-yl) phosphonate derivatives were investigated. Aroyl phosphonates with electron-withdrawing groups generally resulted in better isolated chemical yields. A stoichiometric amount of AlCl3 rather than a catalytic amount was necessary to activate the cycloaddition reaction. The amount of AlCl3 catalyst and its effect on LUMO of ethyl ester benzoyl phosphonate were also investigated by performing density functional theory (DFT) (B97D/6-31+G(d,p)) computations in dichloromethane. An increased loading of AlCl3 induced a considerable decrease in the LUMO energy of ethyl ester of benzoyl phosphonate. The computed Gibbs free activation energy is 17.03kcal/mol in DCM at 0 degrees C using the same computational level.Öğe Synthesis of tertiary propargylic phosphonates by addition of trialkynylaluminum reagents to acyl phosphonates and investigation of their antimicrobial activities(Tubitak Scientific & Technological Research Council Turkey, 2014) Hossain, Mohammad Shakhawoat; Cakir, Sidika Polat; Karaduman, Ayse Betul; Yamac, Mustafa; Demir, Ayhan SitkiA series of propargylic alcohols containing phosphonates was synthesized by addition reactions of tris-(propynyl) and tris-(phenylethynyl) aluminum reagents to acyl phosphonates in good yields. Aromatic moieties of the acyl phosphonates with electron-withdrawing groups generally resulted in better isolated chemical yield. Selected propargylic phosphonates were tested for antimicrobial activities. Compounds 3a and 3h showed noticeable antifungal activity, especially against molds.