Synthesis, Characterization, Molecular Docking, and Investigation of Antibacterial Properties of New Derivatives of 1-H-Phenanthro [9,10-d] Imidazole.

In this study, several imidazole derivatives in one pot multicomponent reaction from various aldehydes 1(a-z), 9,10-phenanthrenequinone, or benzyl (2), and ammonium acetate (3) were synthesized in the presence of acetic acid (AcOH) under reflux conditions at 120 °C. Also, the photochromic properties of synthesized compounds were investigated in AcOH as a solvent under laboratory conditions at a temperature of 120 °C. Moreover, the antibacterial activity of the synthesized compounds was investigated. The structure of the products was confirmed using FT-IR, UV-Vis, 1H-NMR, and 13CNMR spectroscopy. The antimicrobial activity of these compounds against gram-positive bacteria including Bacillus subtilis (B. subtilis) and gram-negative bacteria including Escherichia coli (E.coli) bacteria was evaluated by the Well diffusion (WD) method, and the compounds 4 o showed significant results for both antibacterial activity. To gain insight into how these compounds interact with two types of targets, i. e., human topoisomerase II alpha (5GWK) and acetylcholinesterase (7AIX), binding calculations have been used that provide significant results for both targets and show that most ligands can effectively bind to cleft nucleotides. Interfere in the first one or be well placed in them. Hydrophobic pocket in the dimension, which can ultimately lead to high scores achieved.

Effect of thyme essential oil and its two components on toxicity and some physiological parameters in mulberry pyralid Glyphodes pyloalis Walker.

Extensive usage of synthetic pesticides has proved to be destructive to all living being and the resurgence of pest resistance. Compounds derived from certain plants are usually safer compared to chemical control of pest. The present study thus intended to use Thymus vulgaris essential oil (EO) and two of its derivatives including thymol and carvacrol in order to see their deleterious effects on Glyphodes pyloalis (Walker). We also studied the oil components. This pest has recently become a serious concern for the silk industry. Our results showed that the thyme EO contain several components including thymol (26.9%), ρ-Cymene (14.54%), linalool (13.39%) and carvacrol (5.7%). Our toxicity tests revealed an estimated LD50 values for thyme EO, thymol and carvacrol 2.82, 32.18 and 56.54 µg/larva, respectively. However, the thyme EO was more toxic than its two tested compounds. The activity of certain detoxifying enzymes such as α- and ß-esterase, glutathione S-transferase and cytochrome P450 were significantly inhibited by thymol-treated larvae compared to the control group. Similarly, the activity of alanine aminotransferase, aspartate aminotransferase, lactate dehydrogenase and alkaline phosphatases enzymes in thymol-treated larvae decreased while the activity of acid phosphatases increased. Our results suggest that thyme EO and its components have potential for the control of G. pyloalis larvae in mulberry orchards, where no synthetic chemicals are allowed.

[TBP]2SO4 ionic liquid catalyst for 4MCR of pyridazinoindazole, indazolophthalazine and pyrazolophthalazine derivatives.

Tetrabutyl phosphonium sulfate ([TBP]2SO4), as novel room-temperature ionic liquid (RTIL), was synthesized by a simple cost-effective method, characterized by 1H, 13C, 31P NMR and FT-IR spectrophotometry. The newly prepared catalyst was used as an efficient catalyst in some four multicomponent reactions (4MCRs) e. g., to synthesis pyridazino[1,2-a]indazole, indazolo[2,1-b]phthalazine and pyrazolo[1,2-b]phthalazine. This green method has several advantages such as short reaction time, using simple methods to prepare catalysts and products, easy operation and high efficiency of products. In addition, the catalyst can be easily recovered and reused several times with reduced average activity.

Drug delivery system for controlled release of empagliflozin from alginate-chitosan nanocarrier system.

A biocompatible nanocarrier system was prepared in this research through the reaction of calcium alginate (CA) with chitosan (CS). The structure of developed nanocarriers (CS-CA) was characterized by thermogravimetric analysis (TGA), Fourier transforms infrared (FT-IR) spectroscopy, field emission scanning electron microscopy (FE-SEM), X-ray diffraction (XRD) atomic force microscopy (AFM), and transmission electron microscopy (TEM). Swelling properties of CS-CA and CA, and their ability for loading and in vitro release of empagliflozin (EMP) were also investigated. The results showed the higher loading capacity of CS-CA compared to CA. For both nanocarriers, the drug release was higher at neutral pH (7.4 and 6.8) when compared to acidic pH (1.2). Despite the higher release of CA than CS-CA, the latter exhibited a favorable sustained drug release in all pH levels. As a result, CS-CA nanocarrier (EMP@CS-CANC) can be suggested as a new candidate for colon drug delivery of EMP.

Introducing new and effective catalysts for the synthesis of pyridazino[1,2-a]indazole, indazolo[2,1-b]phthalazine and pyrazolo[1,2-b]phthalazine derivatives.

In this study, a new and effective catalyst for the synthesis of pyridazino[1,2-a]indazole, indazolo[2,1-b]phthalazine and pyrazolo[1,2-b]phthalazine derivatives was introduced. Triethanolammonium acetate ([TEAH][OAc]) accelerates the reaction in a one-pot and four-component condensation of aldehydes, hydrazine hydrate, succinic/phthalic anhydride, and 1,3-dicarbonyl compounds. The yield of the products is high, and the reaction conditions are mild and solvent-free. Furthermore, the model reaction was conducted in the presence of triethanolammonium sulphate ([TEAH][HSO4] and triethanolammonium formate ([TEAH][HCOO]) under various conditions. In addition, the catalyst is recyclable, therefore, it can be reused several times. The structure of the obtained products was confirmed by comparing the M.P., IR, and 1H NMR. Advantages of this technique are as following:•Synthesis of novel, green, and one-pot and four-component condensation (4CC) under solvent-free conditions at room temperature.•The catalytic reaction is performed under mild and environmentally friendly conditions in short reaction times and excellent yields.•The catalyst is easily recycled and exhibits good chemical and structural stability.

Selective immediate detection of Cu2+ by a pH-sensitive rhodamine-based fluorescence probe in breast cancer cell-line.

A biocompatible fluorogenic chemosensor (N-(3-carboxy acryloyl)) rhodamine B (RHA) comprising a furan-2,5-dione receptor and a rhodamine fluorophore via an iminohydrazine crosslinker has been prepared for more scrutinizing optical properties and utilization in molecular imaging of living cells. The consequences indicated that RHA not only is a good pH indicator in acidic media but also can be used as a great sensitive fluoroionophore with high selectivity. The fluorescence emission of the molecule RHA is quite stable in the presence of 15 diverse cations, 18 anions (especially H2PO4-, S2, and F-), and 5 amino acids with the different functional group as a model, except Cu2+ ions with observable emission intensity changing. The Cu2+ probe has a dual functional effect, an "on-off" mechanism in solvent media, and an "off-on" mechanism in Phosphate Buffered Saline (PBS) in acidic pH conditions. The detection limits for Cu2+ in acetone-water media was 0.69 µM and 0.18 µM in pH = 5.0. Moreover, RHA can fluorescently and colorimetrically image Cu2+ ions in acidic and neutral pH with low cytotoxicity in living cells.

A comparative study on the nanoparticles for improved drug delivery systems.

Nanoparticles have attracted considerable recent interest for diverse biomedical applications because of the unique properties of the nanomaterials. It is already known that one of the major advances in the relative application of nanoparticles is the recognition of the steric stabilization which can increase the particle stability in the biological environment and provide the opportunities of the application of nanoparticles in the development of drug delivery systems (DDSs) for achieving drug targeting and controlled drug release. To facilitate their use in such applications, the appropriate design of surface ligands on these nanoparticles is necessary. In view of these, functionalized nanoparticles through surface modification can be utilized to specifically interact with the target molecules on the cell membrane or intracellular ones. This review briefly presents self-assembled nanoparticles with molecules of therapeutic significance with two strategies. The first strategy attempts to improve the placement of the drugs using conjugating the appropriate ligands or adding targeting moieties to the DDS. The second strategy utilizes trigger-controlled drug-release, which restricts drug release at the targeted site to kill cancer cells by externally controlled mechanisms. Among external stimulations, conveniently light has attracted much interest because it, as an orthogonal external stimulus, gives spatiotemporal control of payload release.

Facile synthesis and biological assays of novel 2,4-disubstituted hydrazinyl-thiazoles analogs.

A convenient, one-pot multi-component synthesis of new 2,4-disubstituted hydrazinyl-thiazoles was accomplished using different aldehydes/ketones, thiosemicarbazide, and 4-methoxy phenacyl bromide in the presence of a catalytic amount of AcOH in EtOH. Products were obtained in reasonable yields and high purity. The in vitro antioxidant activity of hydrazinyl-thiazoles was evaluated by DPPH radical scavenging activity in comparison to ascorbic acid. Synthesized thiazoles 14c and 14g possessed the lowest IC50 values. Also, hydrazinyl-thiazoles were screened for their in vitro antibacterial activity against six strains of bacteria including S. aureus, M. luteus, E. coli, Ps. aeruginosa, B. subtilis, and A. hydrophila where some products showed good antibacterial activity. Moreover, compound 14a showed anticancer activity against melanoma cancerous cell lines A375 with LC50=0.55 mg/ml, slightly selective versus normal cell lines (Hu-2) with LC50=1.19 mg/ml..

One-pot multi-component synthesis of 1,4-dihydropyridines using Zn(2+) @KSF and evaluating their antibacterial and antioxidant activities.

New 5-aryl-10-(4-(4-methoxyphenyl)thiazole-2-yl)-9,10-dihydropyrido[2,3-d:5,6-d']dipyrimidinone-2,4,6,8-(1H,3H,5H,7H)-tetraones 6a-d were synthesized through one-pot four-component reaction of aldehydes, barbituric acid, and thiazole using Zn(2+) @KSF under reflux condition. The key features of this reaction are: incorporating four heterocyclic rings, using a heterogeneous and efficient catalyst, high yield, and easy-to-setup reaction. The structure of the products was confirmed by FT-IR, (1)H NMR, and (13)C NMR spectra. The antibacterial activities of compounds 6a-d were screened against Escherichia coli, Micrococcus luteus, Pseudomonas aeruginosa, and Staphylococcus aureus bacterial strains using the zone inhibition method. Also, the 2,2-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activities of compounds 6a-d were evaluated. All compounds showed good antioxidant capacity in comparison to ascorbic acid. The IC50 values of the antioxidant activity were calculated. The proposed mechanism for antioxidant activity is discussed.

Effects of 4-hexylresorcinol on the phenoloxidase from Hyphantria cunea (Lepidoptera: Arctiidae): In vivo and in vitro studies.

Insecticidal effects of 4-hexylresorcinol, a phenoloxidase (PO) inhibitor, were determined on Hyphantria cunea (Drury) under laboratory conditions. The LC50 for the 15-d-old larvae was estimated to be 2.95 g/L after 96 h exposure. The activities of glutathione S-transferase (GST) and PO showed a decrease in larvae treated with 4-hexylresorcinol, and the IC50 of GST and PO were estimated to be 0.8 and 0.43 g/L, respectively, 24 h after treatment. The PO from the hemolymph of fall webworm was purified by ammonium sulfate precipitation, gel-filtration, and ion-exchange chromatography, and then enzymatic characteristics and the mechanism of inhibition were determined using L-dihydroxyphenylalanine (L-DOPA) as the substrate. The purified PO showed a single band on SDS-PAGE with a molecular weight of about 70 kDa. The optimum pH for PO activity was observed at pH 7.0, optimum temperature was found to be 45 °C, and PO activity was strongly inhibited by Zn(2+) . IC50 values were estimated to be 8.2, 19.14, and 24.04 µmol/L for 4-hexylresorsinol, kojic acid, and quercetin, respectively. The inhibitory potencies (i.e., I50 of each compound/I50 of 4-hexylresorcinol) of kojic acid and quercetin on H. cunea PO were estimated to be 1.87 and 2.89, respectively. 4-hexylresorcinol was determined to be a competitive inhibitor, and kojic acid and quercetin were determined to be mixed inhibitors. PO is one of the most important enzymes in an insect's immune system, and the use of PO inhibitors seems to be a promising approach for pest control due to their potential safety for humans.

Facile regioselective synthesis of novel bis-thiazole derivatives and their antimicrobial activity.

The design and synthesis of several new bis-thiazoles 4a-h serving as bis-drugs in comparison with mono-heterocyclic analogs are described. These bis-drugs present superior medicinal and pharmacological activities against both gram-negative (Pseudomonas aeruginosa and Escherichia coli) and gram-positive (Micrococcus luteus and Bacillus subtilis) bacteria, which are in general more sensitive to compounds with higher hydrophobicity. Compounds with higher hydrophobicity (4d and 4h) exhibited some activity against the gram-negative bacteria.

Facile regioselective synthesis of novel bioactive thiazolyl-pyrazoline derivatives via a three-component reaction and their antimicrobial activity.

A series of novel 2-(3,5-diphenyl-4,5-dihydro-1H-pyrazol-1-yl)-4-phenylthiazoles have been prepared by a three-component cyclo-condensation of various chalcones, thiosemicarbazide and phenacyl bromide. The easy work-up of the products, rapid reaction, and mild conditions are notable features of this protocol. The reaction was efficiently catalyzed in one-pot by a few drops of HCl in EtOH under reflux conditions providing the title compounds in moderate to high yields. The antibacterial activity of the selected products was examined. Some products exhibit promising activities.

Synthesis and structure-behavior relationships of tetra-substituted imidazole derivatives of 1,3-diazabicyclo[3,1,0]hex-3-ene.

Among photochromic compounds 1,3-diazabicyclo[3.1.0]hex-3-ene derivatives are currently the subject of intense research due to their photochromic behavior particularly in the crystalline state. In this work, the click syntheses of photochromic compounds containing tetrasubstituted imidazole moieties have been investigated. The structure-photochromic behavior relationships of these compounds have been evaluated.