Fatty acid hydrazides in heterocyclic synthesis: Synthesis of 1,2‐diazepine and pyridazine derivatives

1,2‐Diazepinone derivatives 6a–d, 8a,b, and 10a–c were synthesized from the reaction of olefines carrying EWG as ethoxymethylene malononitrile, ethoxymethylene cyanoacetate, and tetracyanoethylene with 1a–f respectively. Also, 5‐alkyl‐6‐oxotetrahydropyridazine‐4,4‐dicarboxylate derivatives 12a–c were afforded via the reaction of 1d–f with diethyl ethoxymethylene malonate. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:259–264, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20294     

Microwave Irradiation and Glutamic Acid-Assisted Phytotreatment of Tannery and Surgical Industrial Wastewater by Sorghum

We investigated how different doses of microwave irradiation (MR) affect seed germination in Sorghum, including the level of remediation against textile and surgical wastewater (WW) by modulating biochemical and morpho-physiological mechanisms under glutamic acid (GA) application. The experiment was conducted to determine the impact of foliar-applied GA on Sorghum under wastewater conditions. Plants were treated with or without microwave irradiation (30 s, 2.45 GHz), GA (5 and 10 mM), and wastewater (0, 25, 50, and 100). Growth and photosynthetic pigments were significantly decreased in plants only treated with various concentrations of WW. GA significantly improved the plant growth characteristics both in MR-treated and -untreated plants compared with respective controls. HMs stress increased electrolyte leakage (EL), hydrogen peroxide (H₂O₂), and malondialdehyde (MDA) content; however, the GA chelation significantly improved the antioxidant enzymes activities such as ascorbate oxidase (APX), superoxide dismutase (SOD), peroxidase (POD), and catalase (CAT) both in MR-treated and -untreated plants under WW stress compared with respective controls. The results suggested that the MR-treated plants accumulate higher levels of HMs under GA addition in comparison to the WW-only-treated and MR-untreated plants. The maximum increase in Cd accumulation was observed in the range of 14–629% in the roots, 15–2964% in the stems, and 26–4020% in the leaves; the accumulation of Cu was 18–2757% in the roots, 15–4506% in the stems, and 23–4605% in the leaves; and the accumulation of Pb was 13–4122% in the roots, 21–3588% in the stems, and 21–4990% in the leaves under 10 mM GA and MR-treated plants. These findings confirmed that MR-treated sorghum plants had a higher capacity for HMs uptake under GA and could be used as a potential candidate for wastewater treatment.     

Design and Synthesis of Some New Furan-Based Derivatives and Evaluation of In Vitro Cytotoxic Activity

New furan-based derivatives have been, designed, synthesized, and evaluated for their cytotoxic and tubulin polymerization inhibitory activities. DNA flow cytometric study of pyridine carbohydrazide 4 and N-phenyl triazinone 7 demonstrated G₂/M phase cell cycle disruptions. Accumulation of cells in the pre-G1 phase and positive annexin V/PI staining, which may be caused by degeneration or fragmentation of the genetic components, suggested that cell death occurs via an apoptotic cascade. Furthermore, compounds 4 and 7 had a strong pro-apoptotic impact through inducing the intrinsic mitochondrial mechanism of apoptosis. This mechanistic route was verified by an ELISA experiment that indicated a considerable rise in the levels of p53 and Bax and a drop in the level of Bcl-2 when compared with the control.     

Design,Synthesis and Cytotoxic Activity Evaluation of Newly Synthesized Amides-Based TMP Moiety as Potential Anticancer Agents over HepG2 Cells

A novel series of amides based TMP moiety was designed, synthesized and evaluated for their antiproliferative as well as enzyme inhibition activity. Compounds 6a and 6b showed remarkable cytotoxic activity against HepG2 cells with IC₅₀ values 0.65 and 0.92 μM, respectively compared with SAHA and CA-4 as reference compounds. In addition, compound 6a demonstrated good HDAC-tubulin dual inhibition activity as it showed better HDAC activity as well as anti-tubulin activity. Moreover, compound 6a exhibited G2/M phase arrest and pre-G1 apoptosis as demonstrated by cell cycle analysis and Annexin V assays. Further apoptosis studies demonstrated that compound 6a boosted the level of caspase 3/7. Caspase 3/7 activation and apoptosis induction were evidenced by decrease in mitochondrial permeability suggesting that activation of caspase 3/7 may occur via mitochondrial apoptotic pathway.     

A convenient green synthetic approach to the synthesis of novel bioactive selenolo[2,3-c]pyrazoles as antibacterial and antifungal agents

A series of new pyrimidine, triazine, and isoindole heterocycles fused to the selenolopyrazole ring system was synthesized by various condensation reactions of the amino selenolopyrazole carboxamide 1 , which was performed by a new green methodology. The pyrimidinone compound 6 was used as a versatile precursor for several aromatic nucleophilic substitution reactions to produce the sulfanyl pyrimidines 10a-c and the corresponding amines 11a-c and 12a , b . Assignment of the chemical structures for the newly synthesized compounds was confirmed by elemental and spectral analyses including Fourier transform infrared (FTIR), ¹H-NMR, and ¹³C-NMR and mass spectroscopy for some of them. Furthermore, some of these compounds were screened against various pathogenic bacterial and fungal strains. Their results demonstrated that some of them revealed remarkable antimicrobial activities.     

Use of iodide and silver/sulfide ion-selective electrodes for the determination of some tertiary amines and alkaloids

Summary Some tertiary amines and alkaloides were determined by reaction with methyl iodide at 43 °C. The produced quaternary ammonium iodide salts were potentiometrically titrated with standard silver nitrate solution using either the iodide or silver/sulfide ion-selective electrode. The effects of solvent, temperature and time of reaction were examined. An average recovery of 99.0% and 98.9% with standard deviations of 0.73 and 0.52 were obtained for the studied amines and alkaloides, respectively.

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Verwendung der Iodid-bzw. Silber/Sulfid-selektiven Elektrode zur Bestimmung einiger tertiärer Amine und Alkaloide

     

Fluorimetric determination of iron(III) by quenching the luminescence of the zinc-morin-Triton X-100 system

Summary Simple and highly sensitive fluorimetric methods for iron determination are described. The methods are based on quenching the fluorescence of an aqueous morin solution or zinc-morin-Triton X-100 ternary system. The fluorescence emission is measured at 500 and 503 nm (wavelength of excitation 420 and 433 nm) for morin and the ternary system, respectively. The quenching calibration graphs are linear over the range 0–250 and 0–55 ng Fe/ml and the iron detection limits are 20 and 5 ng/ml using morin and zinc-morin-Triton X-100 system, respectively. The influence of experimental variables such as pH, reagent and surfactant concentrations, temperature, standing time and diverse ions are studied to obtain the optimum conditions. The method has been applied to the determination of iron in aluminium metal.

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Fluorimetrische Eisen(III)-bestimmung durch Luminescenzlöschung des Systems Zink-Morin-Triton X-100

     

Formal aza-Michael additions to tropone: Addition of diverse aryl- and alkylamines to tricarbonyl(tropone)iron and [(C7H7O)Fe(CO)3]BF4

A formal aza-Michael addition to tropone by way of tricarbonyl(tropone)iron and/or the tetrafluoroborate salt formed via protonation of the complex is reported. Tricarbonyl(tropone)iron smoothly undergoes the direct aza-Michael reaction with unhindered aliphatic amines under solvent free conditions in good yields. Meanwhile, the known cationic complex [(C₇H₇O)Fe(CO)₃]BF₄ (whose reaction with a small number of nucleophiles was previously reported) undergoes addition with an even broader array of amine nucleophiles. Finally, it was discovered that protecting the aza-Michael adduct as a carbamate was necessary for oxidative demetallation of the complex.