Yazar "Yaglioglu, Ayse Sahin" seçeneğine göre listele

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    Gabriel-Cromwell aziridination of amino sugars; chiral ferrocenoyl-aziridinyl sugar synthesis and their biological evaluation
    (Elsevier Sci Ltd, 2021) Sert, Mustafa; Isilar, Ozer; Yaglioglu, Ayse Sahin; Bulut, Adnan
    N-sugar substituted chiral aziridines were synthesized via Gabriel-Cromwell reaction. Novel pure diastereomers of aziridine derivatives (4 diastereomers) were readily obtained in high yields and their structures were confirmed by means of 1H NMR, 13C NMR, FT-IR, Mass and optical rotations. This is, to the best of our knowledge, the unique example of N-sugar aziridine synthesis. Diastereomeric effects for prostate (PC3) and cervix (HeLa) cancers were screened and it has been observed that the epimers bearing the same sugars showed different results against PC3 and HeLa cancer cells. The novel sugar aziridines were investigated as promising prodrug candidates for prostate cancer (PC3) therapy. Moreover, the drug likeness calculations (Lipinski's rule, physicochemical properties, lipophilicity, solubility, pharmacokinetics and bioavailability radar) have indicated that the sugar aziridines can be good candidates as oral drugs.
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    Öğe
    Novel Tricyclo[4.2.1]Nonane and Bicyclo[2.2.1]Heptane Derivatives: Synthesis, in Vitro Biological Activities and in Silico Studies
    (Wiley-V C H Verlag Gmbh, 2024) Sarikaya, Meryem Kececi; Yaglioglu, Ayse Sahin; Ceylan, Mustafa; Yirtici, Uemit
    The target benzothiazole derivatives (8a-g) were synthesized starting from norbornene. The addition of dichloroketene to norbornene followed by the reduction of chlorine atoms were synthesized tricyclo[4.2.1.02,5]non-7-en-3-one (4). The condensation of benzaldehyde derivatives with compound 4 were obtained chalcone analogs (6a-g). Finally, benzothiazole derivatives (8a-g) were obtained by the reaction of the chalcone analogs with 2-aminobenzothiol in an acidic medium. The antiproliferative activities of compounds 6a-g and 8a-g were determined against C6 (rat brain tumor) and HeLa (human cervical carcinoma) cell lines using a BrdU cell proliferation ELISA assay with 5-fluorouracil (5-FU) as a standard. In both series, when compared with 5-FU (IC50=3.8 mu M for C6 and 16.33 mu M for HeLa), the most active compounds against C6 cells were 6a and 8g with IC50 values of 14.13 mu M and 29.99 mu M, respectively. With this, 6a, 6e, 6f, and 8b were the most active compounds against HeLa cells with IC50 values of 0.8, 1.21, 19.33 and 18.13 mu M, respectively. Additionally, the SwissADME online web tool was used to predict the physicochemical and ADME properties of the tested compounds. The results showed that all compounds possess promising predicted physiochemical and pharmacokinetic properties and comply with Lipinski's rule of 5, indicating that they are predicted to be orally bioavailable that they possess a predicted bioavailability score of 0.55. Furthermore, in the SwissADME Boiled-Egg chart, all compounds showed high predicted GIT absorption, while compounds 6a-g showed blood-brain barrier (BBB) permeation, and compounds 8a-g did not. Moreover, none of the compounds was (P-gp) substrates. This study investigated the potential interactions between the antiapoptotic proteins Bcl-2, Bcl-xl, Bcl-w, Brag-1, Bfl-1, and Mcl-1 and compounds 6a, 8b, and 8g through molecular docking studies. The findings suggest that these compounds may effectively inhibit antiapoptotic proteins, as evidenced by significant hydrogen bonds and hydrophobic interactions, particularly with Bcl-xl.
  • Küçük Resim
    Öğe
    Synthesis and biological evaluation of novel urea, thiourea and squaramide diastereomers possessing sugar backbone
    (ELSEVIER SCI LTD, 2020) Isilar, Ozer; Bulut, Adnan; Yaglioglu, Ayse Sahin; Demirtas, Ibrahim; Arat, Esra; Turk, Mustafa
    A series of novel chiral 14 urea, thiourea and squaramide stereoisomers possessing carbohydrate backbones as well as amide functional groups was synthesized and characterized by their, H-1 NMR, C-13 NMR, FT-IR, HRMS, optical rotation, and melting points. Their antiproliferative activities were investigated against HeLa and PC3 cell lines. The compounds 9, 11 and 12 showed better activities at 25 mu M against PC3 cell line with respect to the standard 5-fluorouracil (5-FU). Especially, the compounds 9 and 11 showed higher activities than the standard 5-FU even at low concentration (5 mu M) against HeLa cell line. IC50 results also confirm these activities. The compounds 9, 10 and 11 have the IC50 values of 1.10 mu M, 1.51 mu M and 1.02 mu M, respectively while 5-FU has 2.51 mu M. Moreover, their cytotoxicity tests have proven that their viabilities were in between 50% and 100%.