Synthesis of new aromatic phosphoramidates under a three-component reactionGarcía-Aranda, Mónica I.; Franco-Pérez, Marco; Bonilla-Landa, Israel; Castrejón-Flores, José Luis; Zamudio-Medina, Angel
doi: 10.1080/10426507.2022.2053854pmid: N/A
Abstract A fast, safe and accessible multicomponent reaction procedure is reported for the synthesis of symmetric and nonsymmetric benzyl-bisphosphoramidate derivatives. Our key reagents were 1,3-phenylenedimethanamine 3 conjointly with the five different phosphorous chlorides, O, O′-diethyl chlorothiophosphate 1, diphenyl phosphoryl chloride 2, diethyl chlorophosphate 5, N, N, N ′, N′-tetramethylphosphorodiamidic chloride 7 and O, O′-dimethyl chlorothiophosphate 9. A total of seven products were obtained, five of them none reported before. As far as we know, our work constitutes the first approach for the synthesis of nonsymmetric benzyl-bisphosphoramidate derivatives. The presence of our adducts were always confirmed by NMR spectroscopy (1H, 13C and 31P) and mass spectrometry.
A naphthol-functionalized bis(salamo)-like chromogenic and fluorogenic probe for monitoring hydrogen sulfide and application in water samplesGuo, Wen-Ting; Dou, Lin; Yan, Yuan-Ji; Li, Ruo-Yu; Dong, Wen-Kui
doi: 10.1080/10426507.2022.2046576pmid: N/A
Abstract A naphthol-functionalized bis(salamo)-like chromogenic and fluorogenic probe (TBS) was designed and synthesized for efficient double-channel detection of hydrogen sulfide (H2S). The probe TBS was characterized through various spectroscopic techniques. From both visible light and 365 nm UV light, TBS could have naked-eye recognition of H2S with obvious color change. In comparison with some chemical probes, the probe TBS could selectively monitor H2S with detection limit as low as 0.71 μM, which could serve as a promising candidate for detecting H2S in real world sampling. Beyond that, the sensing mechanism toward H2S was fully validated by 1H NMR, mass spectra (ESI-MS) as well as UV titration. Density-functional theory and time-dependent density-functional theory calculations were also carried out to further explain the photophysical behavior of the probe TBS with H2S. Finally, the probe TBS could be utilized as sulfide-targeted probe in a practical sample.
Synthesis, antiproliferative activity, molecular docking studies of hydrazone functionalised thioparabanic acid and rhodanine analoguesKıbrız, İbrahim Evren; Akkoç, Senem; Sert, Yusuf; Çay, Ümit; Üngören, Şevket Hakan
doi: 10.1080/10426507.2022.2046578pmid: N/A
Abstract Twenty new samples of hydrazone functionalized thioparabanic acid and rhodanine analogues were prepared by reacting a mixture of acyl methylene substituted rhodanine and hydantoin compounds with hydrazine and acyl hydrazine derivatives in good yields (53–89%). The cytotoxic effect of newly synthesized compounds 3a–g, 4a–m was evaluated on the human colon cancer cell line (DLD-1) and human liver cancer cell line (HepG2) by comparison with cisplatin as a positive control drug. Two of the molecules (3f [2-hydroxy-N'-((Z)-1-(5-oxo-2-thioxoimidazolidin-4-ylidene)propan-2-ylidene)benzohydrazide], 3g [(5Z)-5-(2-(2-(3,4-dimethylphenyl)hydrazono)propylidene)-2-thioxoimidazolidin-4-one]) showed significant inhibition on cancer cells. Particularly, one of the molecules (3f) was found to be more effective than cisplatine with IC50 values of 4.71 µM and 2.79 µM for DLD-1, HepG2, respectively. Selectivity of the most active five compounds was screened against a healthy human cell line (Wl-38). Compounds 3g and 4l, which are, respectively, thioparabanic acid and rhodanine derivatives, demonstrated good selectivity, and it was observed that the toxic effect of these compounds was more on colon and liver cancer cells than on normal lung cells. The molecular docking evaluations for active 3f and 3g molecules on the liver and colon cancer were conducted to support the obtained experimental results with the in silico AutoDock Vina program and the results were shown to support each other.
Extracellular azo dye oxidation: Reduction of azo dye in batch reactors with biogenic sulfideToprak, Dilan; Demir, Özlem; Uçar, Deniz
doi: 10.1080/10426507.2022.2046579pmid: N/A
Abstract In this study, the sulfide-based reduction of azo dyes (Acid Blue 264) was investigated. Sulfate was reduced to sulfide with an ethanol-fed sulfate reduction reactor and the sulfide produced was used to reduce azo dyes in separate batch reactors using sulfide as the electron carrier. The Box–Behnken experiment design method was used to identify how operational parameters affect the decolorization efficiency. As independent variables, initial dye concentration, sulfide concentration and reaction time were selected while dye removal was considered as the response function. Based on the Box Behnken design, the higher regression coefficient (R2=0.9397) shows that the experimental results are in good agreement with model predictions. At the initial dye concentration of 80 mg/L, the highest dye removal efficiency, about 82.39%, was obtained at the sulfide concentration of 50 mg/L and the reaction time of 25 h. This study showed that Box Behnken’s model prediction was a suitable approach for identifying the best conditions for dye removal.
Design, synthesis and nematocidal activity of novel 1,2,4-oxadiazole derivatives with a 1,3,4-thiadiazole amide moietyLiu, Dan; Wang, Zhengxing; Zhou, Jing-Jiang; Gan, Xiuhai
doi: 10.1080/10426507.2022.2046580pmid: N/A
Abstract A series of novel 1,2,4-oxadiazole derivatives containing 1,3,4-thiadiazole amide group was synthesized and their nematocidal activities were evaluated. The results indicated that compounds 4-methoxy-N-(5-(((3-(p-tolyl)-1,2,4-oxadiazol-5-yl)methyl)thio)-1,3,4-thiadiazol-2-yl)benzamide 4i and N-(5-(((3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl)methyl)thio)-1,3,4-thiadiazol-2-yl)benzamilde 4p showed good nematocidal activity against Bursaphelenchus xylophilus. The corrected mortality of compounds 4i and 4p at 200 mg/L was 57.1% and 60.1%, respectively, which are much better than 13.5% of the commercial seed coating agent Tioxazafen. Compounds 4i and 4p dramatically decreased the head swinging, body fluctuation, and body bending frequency of B. xylophilus after 12 h of treatment. Moreover, they inhibited the respiration, decreased the oxygen consumption, and caused fluid leakage of B. xylophilus. In addition, compounds 4i and 4p have good druggability properties similar to those of Tioxazafen. The present work indicates that compounds 4i or 4p could be promising lead compounds for further development of nematicides.
Synthesis and characterization of some 2-quinonyl piperazine derivativesSahinler Ayla, Sibel; Pasaoglu Gonul, Gulay
doi: 10.1080/10426507.2022.2047968pmid: N/A
Abstract The synthesis of a series of some piperazine derivatives with quinone moiety was carried out in present study. Obtained 2-quinonyl piperazine derivatives were then reacted with some aliphatic or aromatic thiol nucleophiles and new N,S-substituted of 1,4-naphthoquinone synthesized. The structures of novel molecules were elucidated by microanalysis and spectroscopic methods such as FT-IR, 1H-NMR, 13C-NMR, UV-Vis. Mass and MS/MS fragmentation studies were also performed and fragmentation pathway of protonated novel piperazine derivatives were proposed.
Organotin(IV) complexes derived from hydrazone ligands: Synthesis, spectral analysis, antimicrobial and molecular docking studiesKumar, Naresh; Asija, Sonika; Deswal, Yogesh; Saroya, Sonia; Kumar, Ashwani; Devi, Jai
doi: 10.1080/10426507.2022.2048386pmid: N/A
Abstract The goal of this research work is to create a new class of diorganotin(IV) complexes with general formula R2SnL1-4, where R = CH3, C2H5, C4H9 & C6H5, and L1-4 are the Schiff base ligands derived from the condensation of indole-3-acetic acid hydrazide with salicylaldehyde derivatives in 1:1 molar ratio. Various spectral (FTIR, NMR and mass spectrometry) and physico-chemical (XRD, TGA) techniques were utilized to identify the structure of the prepared compounds. Spectroscopic evidence suggests that Schiff base ligands coordinate to the central tin atom in a tridentate manner with ONO as the donor site, thus forming a pentacoordinate environment around the metal ion. The serial dilution method was employed for carrying out the antimicrobial activity of the produced compounds against four bacterial strains and two fungal strains. The observed results of biocidal activity showed that compounds Ph2SnL3 (16) and Ph2SnL4 (20) were found to be most potent against the tested strains. Further, molecular docking studies for active compounds i.e., 16 and 20 were carried out in the active site of Escherichia coli 3-oxoacyl-[acyl-carrier-protein] synthase 2 (FabF). To check the drug-likeness, in silico studies of the synthesized compounds was carried out and it has been found that compounds can be used as orally active drugs.
Synthesis of antibiotic-modified silica nanoparticles and their use as a controlled drug release system with antibacterial propertiesYilmaz, Betul; Ozay, Ozgur
doi: 10.1080/10426507.2022.2049267pmid: N/A
Abstract In this study, monodispersed silica nanoparticles were synthesized using the Stöber method. The synthesized nanoparticles underwent a range of surface modifications and were converted to nanoparticles with drug release and antibacterial features. For modification, firstly –NH2 groups were created on the silica nanoparticle surface using (3-Aminopropyl)triethoxysilane (APTES). In the second stage, hexachlorocyclotriphosphazene (Phz) molecules were bound to the silica nanoparticle surfaces due to these amino groups. In the final stage of modification, the chloride groups in the hexachlorocyclotriphosphazene structure were modified with trimethoprim (TMP) and nanoparticles with antibacterial properties were obtained. The modified silica nanoparticles were characterized with scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), Fourier transform infrared spectroscopy (FT-IR), Transmission Electron Microscopy (TEM), and Thermogravimetric analysis (TGA). The silica-based nanoparticles were used for release of rhodamine 6G, chosen as a model drug. As a result of the drug release studies, the modified silica nanoparticles were found to abide by the Korsmeyer–Peppas low power model and non-Fickian release mechanism as release model. Additionally, nanoparticles both loaded and not loaded with the model drug were determined to have antibacterial properties against Escherichia coli, Bacillus subtilis, and Staphylococcus aureus bacteria.