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    Phosphorus-nitrogen compounds. part 38. Syntheses, characterizations, cytotoxic, antituberculosis and antimicrobial activities and DNA interactions of spirocyclotetraphosphazenes with bis-ferrocenyl pendant arms
    (Elsevier Science Sa, 2017) Elmas, Gamze; Okumuş, Aytuğ; Cemaloğlu, Reşit; Kılıç, Zeynel; Çelik, Süheyla Pınar; Açık, Leyla; Tunalı, Beste Cağdaş
    The reactions of N4P4Cl8 (1), with two equimolar amounts of N-(1-ferrocenylmethyl)-N-methyl-propylenediamine gave the monoferrocenyl-spiro (as a byproduct), bisferrocenyl-2-trans-6-dispiro (2) and bisferrocenyl-2-cis-6-dispiro (3) cyclotetraphosphazenes. The 2-trans-6-dispiro (2) was reacted with excess monoamines to produce the tetraamino products (2a-2d). The one equimolar amount of the diamines and dialkoxides with 2 afforded the mono-diamino (2e and 2f) and mono-dialkoxy (2g and 2h) cyclotetraphosphazenes. Whereas, excess diamines and dialkoxides with 2 produced the bis-diamino (2i and 2j) and bis-dialkoxy (2k and 2l) bisferrocenyl-2-trans-6-dispirocyclotetraphosphazenes. The structures of the compounds were verified by elemental analyses, ESI-MS, FTIR, HSQC, HMBC, H-1, C-13, and P-31 NMR techniques. The molecular structures of 2 and 2b were established by X-ray crystallography. Compounds 2e and 2f have two stereogenic P-atoms. Additionally, the structures of 2i-2l containing tetraspiro rings in the skeletons look similar a propeller. The Fc groups of the cyclotetraphosphazenes were found to be redox active with two-reversible electron oxidations. The antimicrobial activity of the compounds was examined against some bacteria and yeast strains. The interactions of the compounds with DNA revealed that the compounds caused conformational changes even strand break on super-coiled DNA helix. Furthermore, the compounds (except 2, 2a and 2d) inhibited DNA restriction indicating compounds binding to A/A and G/G nucleotides of the DNA. The evaluations of the cytotoxic activity against L929 fibroblast and DLD-1 colon cancer cell lines were carried out. Some of the compounds were evaluated for antituberculosis activity against reference strain Mycobacterium tuberculosis H37Rv, and 2i and 2l displayed antituberculosis activity against H37Rv. (C) 2017 Elsevier B.V. All rights reserved.
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    Phosphorus-nitrogen compounds. Part 72. Bisspiro(N/N)cyclotri-phosphazenes with 4-chlorobenzyl and ferrocenyl pendant arms: Synthesis, structural characterization, dye-sensitized solar cell fabrication and antituberculosis activity studies
    (Elsevier B.V., 2024) Berberoğlu, İpek; Cemaloğlu, Reşit; Binici, Arzu; Yakut, Mehtap; Asmafiliz, Nuran; Kılıç, Zeynel; Güzel, Remziye; 0000-0002-2802-0754; 0000-0001-7470-4156; 0000-0002-9335-4101
    In this study, dichlorobisspiro(N/N)cyclotriphosphazenes with 4-chlorobenzyl and ferrocenyl-pendant arms were prepared to investigate their spectroscopic and crystallographic characterizations, and antituberculosis activities. The chlorine replacement reactions of tetrachloro(4-chlorobenzyl)spiro(N/N)cyclotri-phosphazenes with ferrocenyldiamines (4 and 5) lead to dichlorobispiro(N/N)cyclotriphosphazenes, containing unsymmetrical diaminospirorings. All cyclotriphosphazenes were characterized by mass spectrometry, FTIR and 31P NMR spectroscopies. Two different stereogenic P-centers are present in the unsymmetrically substituted inorganic-organic fused hybrid rings. These compounds may be in the form of racemic mixtures (RR'/SS' and RS'/SR'). The molecular and crystal structures of trans (6a and 7a) and cis (6b and 7b) isomers were elucidated by single-crystal X-ray structural crystallography. The space groups of trans-6a, cis-6b, trans-7a and cis-7b are centrosymmetric P -1, P bca, P 21/n and P bca, respectively. Therefore, the crystal lattices contain both enantiomers. The absolute configurations of P2 atoms of 6a, 6b, 7a and 7b are R, R, S and S, respectively. It was determined that the most effective compound was 6b against Mycobacterium tuberculosis H37Rv (ATCC 27,294) strain among the phosphazenes 6a, 6b and 10b. Among the compounds, In the reversible cyclic voltammograms of ferrocenyl-dispirophosphazenes, only one oxidation–reduction wave was observed. The HOMO energy values of the compounds were figured out using the oxidation potential (Eox). Whereas, the LUMO energy values were figured out from the optical band gap values using Tauc plots. In addition, it was determined that the most effective compound that can be used in dye-sensitized solar cells (DSSCs) is cis-11b.
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    Phosphorus-nitrogen compounds: Part 76. design and syntheses of dispiro- and trispiro(N/N)cyclotriphosphazenes: Conformational and structural analyses, chirality, electrochemical, dye-sensitized solar cells, and bioactivity studies
    (American Chemical Society, 2024) Cemaloğlu, Reşit; Asmafiliz, Nuran; Tümer, Yasemin; Hökelek, Tuncer; Kılıç, Zeynel; Çelik, Nejla Nur; Açık, Leyla; Güzel, Remziye; Erdal, Gülbahar Güzel
    The reactions of monospirocyclotriphosphazenes (1 and 2) with N-methyl-1,3-diaminopropane gave unsymmetrical cis-(3 and 5) and trans-(4 and 6) dispirocyclotriphosphazenes. Trans-cis-trans (tct) (7 and 11), cis-cis-cis (ccc) (8 and 12), trans-trans-cis (ttc) (9 and 13), and cis-trans-trans (ctt) (14) trispirocyclotriphosphazenes were obtained from the reactions of 3 and 5 and 4 and 6 with N-methyl-1,3-diaminopropane. cis-Dispirocyclotriphosphazenes (3 and 5) exist as “pseudomesoracemates”, while trans-dispirocyclotriphosphazenes (4 and 6) are in “racemates”. The existences of cis-3 and trans-4 as “pseudomesoracemate” and “racemate” were confirmed by 31P NMR spectra recorded by the addition of “chiral solvating agent (CSA)”. X-ray crystallography proved that the absolute configurations of each enantiomer of cis-5 and trans-6 are SS′ and RS′. Trispirocyclotriphosphazenes tct, ttc, ccc, and ctt exist as racemates, pseudomesoracemate, and meso forms. Furthermore, Hirshfeld surface analysis of the crystal structures of cis-5 and trans-6 revealed that the most significant contribution to crystal packing comes from H···H (58.2 and 57.6%, respectively). An oxidation-reduction wave was detected in the reversible cyclic voltammograms of the phosphazenes. The highest power conversion efficiency in dye-sensitized solar cell studies was obtained with cis-5. Additionally, trans-6 exhibited the lowest minimal inhibitory concentration value (78.1 μM) against Candida tropicalis, and it was observed to cleave pBR322 plasmid DNA.