13 research outputs found
2-Naphthylthio Cyclotriphosphazene Derivatives: Synthesis, Characterization, Crystallographic and Fluorescence Properties
No full textESIPT Aktif Ve İnaktif Sistemleri İçeren Yeni Tip Siklotrifosfazen Temelli Moleküllerin Dizaynı Ve Fotofiziksel Özelliklerinin İncelenmesi
No full textDesigning inorganic–organic hybrid molecules based on carbazole/indole-appended cyclotriphosphazenes and the investigation of their photophysical properties
No full textThe preparation of new fluorescent cyclotriphosphazene compounds and examination of the effect of the substituent on the photophysical properties of the new compounds formed in terms of the number and variety of substituents are attempted in this work. Therefore, cyclotriphosphazene derivatives bearing carbazole and indole moieties (2-9) were synthesized via the nucleophilic substitution reactions of cyclotriphosphazene (1) with N-(2-hydroxyethyl)carbazole (I) and 1-(2-hydroxylethyl)-2-methyl-1H-indole (II) and those of tris nongeminal cyclotriphosphazene derivatives (3a,b and 5a,b) with I and II. The full characterization data of compounds 2-9 were obtained by utilizing mass spectrometry and spectroscopic techniques. The crystal structures of II and 3a were elucidated using the single crystal X-ray diffraction method. The photophysical aspects of the targeted compounds (7a, 8 and 9) were investigated by UV/Vis and fluorescence spectroscopies using different organic solvents, and the results for the targeted compounds were compared within themselves, together with their precursors (I and II). It was seen that compound 7a, which includes both an ethoxycarbazole and an ethoxymethylindole group, has improved photophysical properties when compared with the fully ethoxycarbazole (8) and fully ethoxymethylindole (9) substituted cyclotriphosphazene derivatives
Synthesis of new cyclotriphosphazene derivatives bearing Schiff bases and their thermal and absorbance properties
No full textIn this study, a series of cyclotriphosphazene derivatives containing a Schiff base (3a-3d) were synthesized by the reactions of hexachlorocyclotriphosphazene (1) with bis-aryl Schiff bases (2a-2d) having different terminal groups (H, F, Cl, and Br). The products (3a-3d) were characterized by elemental and mass analyses, FT-IR, and H-1, C-13, and P-31 NMR spectroscopies. Furthermore, the structure of compound 3a was also determined by X-ray crystallography. The thermal behaviors and the spectral properties of the new cyclotriphosphazene compounds (3a-3d) were investigated and the results were compared in the series
New design of cyclotriphosphazene derivatives bearing carbazole units: The syntheses, characterization, and photophysical properties
No full textIn the current work, di- and tetra- aniline substituted cyclotriphosphazene derivatives (1a-b) were prepared from commercially available cyclotriphosphazene and underwent nucleophilic substitution reaction with 9-ethyl-9Hcarbazol-3-ol (2) to produce three new cyclotriphosphazene compounds having two- (3a), three- (4b) and fourcarbazole units (5b), respectively. The full characterization data of the targeted compounds were obtained by utilizing elemental analysis, mass spectrometry, H-1, and P-31 NMR spectroscopies. The structure of compound 3a was further supported by single crystal X-Ray diffraction technique. As the photophysical aspect of the synthesized compounds 3a, 4b and 5b, UV- Vis and steady-state fluorescence spectroscopies were used in different organic solvents. In addition, time-resolved fluorescence and 3D-fluorescence spectroscopies were applied to get deeper information about the photophysical properties of targeted compounds
Unexpected Ring Expansion of a Four-Membered Cyclophosphazane
No full textNucleophilic substitution reactions of the N(R),N(R)-spiro-bridged octachlorobis(cyclotriphosphazene), N3P3Cl4[N(CH2)(5)CH3](2)N3P3Cl4 (1), with sodium salts of alcohols (1,3-propanediol, 2,2,3,3,4,4-hexafluoro-1,5-pentanediol, and phenol) give ansa products (2-4) via an unexpected rearrangement. These products were characterized by elemental analysis, mass spectrometry, and H-1 and P-31 NMR spectroscopy. The molecular structures of compounds 3 and 4 were also established by X-ray crystallography. This new class of phosphazene structures consists of three fused P3N3 rings that arise from expansion of the four-membered phosphazane ring in 1 to a six-membered N3P3 ring during alcoholysis reactions
Novel chloro-substituted thiophene thiosemicarbazone: Synthesis, crystal structures, DFT analysis and antimicrobial evaluation of its Co(II), Zn(II), Ni (II), and Pd(II) complexes
No full textThiosemicarbazones, obtained through the condensation of hydrazine derivatives with carbonyl compounds, constitute an important class of Schiff bases with broad pharmacological potential. In this work, a chloro-substituted thiophene-derived thiosemicarbazone ligand was synthesized from 4-methyl-3-thiosemicarbazide, and its coordination complexes with cobalt(II), zinc(II), palladium(II), and nickel(II) ions were prepared. The synthesized compounds were characterized comprehensively using Fourier Transform Infrared Spectroscopy, Ultraviolet-Visible Spectroscopy, proton Nuclear Magnetic Resonance, mass spectrometry, elemental analysis, molar conductivity, and single-crystal X-ray diffraction. Structural and electronic features were further investigated through density functional theory calculations, which provided insights into orbital distributions, energy gaps, and optimized geometries. Antimicrobial screening demonstrated that the ligand and its metal complexes exhibited significant inhibitory effects against selected bacterial and fungal strains, with enhanced activity observed for the complexes compared to the free ligand. The combined experimental and computational findings highlight the importance of halogen substitution and transition-metal coordination in tuning the biological and electronic properties of thiosemicarbazone derivatives, supporting their potential as promising candidates for future therapeutic development
The investigation of thermosensitive properties of phosphazene derivatives bearing amino acid ester groups
No full textIn this study, a series of phosphazene derivatives having amino acid esters were synthesized from the reactions of amino acid esters with cyclophosphazenes. Hexachlorocyclotriphosphazene, (N3P3Cl16) and octachlorocyclotetraphosphazene (N4P4Cl8) have been reacted with carboxylic amino acid esters; glycine ethyl ester hydrochloride, glycine methyl ester hydrochloride, beta-alanine ethyl ester hydrochloride, B-alanine methyl ester hydrochloride and methyl 6-aminohexanoate hydrochloride to obtain cyclophosphazene compounds containing amino acid esters as side groups. All obtained compounds (1-9) were characterized using spectroscopic methods and elemental analysis. The molecular structures of compounds 2, 5 and 6 were also characterized by X-ray crystallographic studies. Hydrolytic degradations of compounds (1-9) were observed by P-31 NMR spectroscopy under acidic condition (pH = 1-3) and at body temperature (35-38 degrees C). Concentration-dependent lower critical solution temperatures (LCST) of compounds were examined to determine their thermosensitive behaviors in aqueous solution. It is found that all compounds degraded to harmless products such as amino acid, phosphates, ammonium salts. LCSTs of compounds 1, 2 and 6 were found to be around body temperature that is important for biomedical applications. (C) 2017 Elsevier B.V. All rights reserved
New cyclotriphosphazenes with butylated oxyanisole motif; synthesis, characterization and biological properties
No full text<p>In the present work, new cyclotriphosphazene derivatives containing butylated oxyanisole (BA) group (3, 4a/b, 6a/b, 7, 11a/b and 12) were synthesized and characterized with using elemental analysis, mass, and NMR (1H and 31P) spectroscopic techniques in detailed. The molecular and crystal structure of compound 3 was also determined by single-crystal X-ray crystallography. The antimicrobial activities of the compounds (3, 7 and 12) were evaluated against strains of Staphylococcus aureus ATCC 29213 as Gram positive cocci, Bacillus cereus DSMZ 4312 as Gram positive bacilli, Escherichia coli ATCC 8739 as Gram negative bacilli, and Candida albicans ATCC 10231, a dimorphic yeast species representing fungi as well as antioxidant activities of these compounds. In the biological and antioxidant activity tests carried out, compound 3 stood out with both antibacterial and antioxidant activity compared to other compounds.</p>
Synthesis and biological activity of new indole based derivatives as potent anticancer, antioxidant and antimicrobial agents
No full textIndoles have very critical roles to design new biologically active molecules in medicinal chemistry. They display higher biological activities or create new biological properties when compared to the other heteroaromatic compounds. In the present study, 1-ethyl-2-phenyl-3-(thiophen-2-yl)-1H-indole (3), 8-ethyl-8H-benzo[a]thieno[3,2-c]carbazole (4), 1-ethyl-2-phenyl-3-(5-(phenylethynyl)thiophen-2-yl)-1H-indole (6) and 1-ethyl-3-(furan-2-yl)-2-phenyl-1H-indole (7) are prepared via Pd-catalyzed cross-coupling reactions and iodocyclization reactions. It was determined that compound 3 and 7 were also seemed to be better drug candidates at the end of in silico evaluation. Furthermore, compound 7 provided the best antibacterial and antifungal activity against the test indicator strains. It showed a potent antifungal effect on Aspergillus niger ATCC 16404 (MIC: 1.17 mu g mL(-1); MFC: 2.7 mu g mL(-1)). In addition, while compounds 3, 6 and 7 showed significantly high molybdenum reducing activity compared to trolox, 7 exhibited almost the same antioxidant activity (EC50 = 7.1 mu M) compared to the trolox standard (EC50 = 5.07 mu M). After characterization, the cytotoxic activities of novel indoles were tested against different cancer cell lines and non-cancerous human cell line. Compound 3 and 7 had selective cytotoxic activity towards cancer cells. EC50 values of compound 3 were found to be 248.15 mu M for LnCap, 139.81 mu M for HepG2, and 164.72 mu M for the Caco-2 cell line. Similarly, The EC50 value of 7 was found as 38.725 mu M for LnCap, 70.02 mu M for HepG2, and 86.98 mu M for Caco-2, and 90.97 mu M for Hek293 cell line. Moreover, it was revealed that these two compounds showed strong apoptotic properties towards these cancer cell lines as described by image cytometry and real time PCR. Consequently, these results improved that our molecules 3 and 7 could be new candidates as anticancer agents and apoptosis inducers. (C) 2022 Elsevier B.V. All rights reserved.COST Action [CA17104]; Ondokuz Mayis University Research Fund [PYO.ZRT.1904.20.010]; YuzuncuYil University [FBA-2020-8663]The author (A. Kivrak) would like to acknowledge networking contribution by the COST Action CA17104 New diagnostic and therapeutic tools against multidrug resistant tumours. The author (A.Kurt-Kizildo.gan) would like to acknowledge Ondokuz Mayis University Research Fund [Grant No.: PYO.ZRT.1904.20.010] for supporting this study. The author (M.Konus) would like to acknowledge Van YuzuncuYil University (FBA-2020-8663) for supporting this study
