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KARAKUŞ, SEVGİ

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KARAKUŞ

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SEVGİ

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2009 - 20102
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    Synthesis, antiviral and anticancer activity of some novel thioureas derived from N-(4-nitro-2-phenoxyphenyl)-methanesulfonamide
    (ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER, 2009) KÜÇÜKGÜZEL, İLKAY; Karakus, Sevgi; Kucukguzel, S. Guniz; Kucukguzel, Ilkay; De Clercq, Erik; Pannecouque, Christophe; Andrei, Graciela; Snoeck, Robert; Sahin, Fikrettin; Bayrak, Oemer Faruk
    Due to a continuing effort to develop new antiviral agents, a series of 1-[4-(methanesulfonamido)-3-phenoxyphenyl]-3-alkyl/aryl thioureas 3a-i have been synthesized by the reaction of alkyl/aryl isothiocyanates with 4-amino-2-phenoxymethanesulfonanilide. These derivatives were structurally characterized by the use of spectral techniques and evaluated for their anticancer and antiviral activities. None of the tested compounds showed significant anticancer properties on A549 and L929 cell lines. All synthesized compounds 3a-i were evaluated in vitro against HIV-1 (IIIB) and HIV-2 (ROD) strains in MT-4 cells, as well as other selected viruses such as HSV-1, HSV-2, Coxsackie virus B4, Sindbis virus and varicella-zoster virus using HEL, HeLa and Vero cell cultures. Compound 3b was able to block HIV replication with almost 100% maximum protection at 125 mu g/ml, and IC50 values of 54.9 mu g/ml and 65.9 mu g/ml against HIV-1 and HIV-2, respectively. (C) 2009 Elsevier Masson SAS. All rights reserved.
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    2-Propylamino-5-[4-(2-hydroxy-3,5-dichlorobenzylideneamino) phenyl]-1,3,4-thiadiazole: X-ray and DFT-calculated structures
    (SPRINGER/PLENUM PUBLISHERS, 2010) KARAKUŞ, SEVGİ; Suleymanoglu, Nevin; Ustabas, Resat; Alpaslan, Yelda Bingoel; Coruh, Ufuk; Karakus, Sevgi; Rollas, Sevim
    2-Propylamino-5-[4-(2-hydroxy-3,5-dichlorobenzylideneamino) phenyl]-1,3,4-thiadiazole, formulated as C18H16Cl2N4OS (I), was synthesized. The crystal and molecular structure of (I) have been determined by H-1-NMR, IR, and X-ray single crystal diffraction. The compound (I) crystallizes in the monoclinic, space group P2(1)/c with unit cell parameters a = 9.0576(2) , b = 24.3382(8) , c = 9.0585(2) , M (r) = 407.31, V = 1851.13(9) (3), Z = 4, R (1) = 0.036, and wR (2) = 0.096. Molecular geometry from X-ray experiment of (I) in the ground state has been compared using the density functional method (B3LYP) with 6-31G(d) basis set. To determine conformational flexibility, molecular energy profile of (I) was obtained by semi-empirical (PM3) calculations with respect to selected degree of torsional freedom, which was varied from -180A degrees to +180A degrees in steps of 10A degrees. The results are indicative that the Schiff base, which contains a thiadiazole ring, prefers to be in E-configuration. In addition, molecular electrostatic potential, frontier molecular orbitals, and natural bond orbitals analysis were performed by the B3LYP/6-31G(d) method.