Synthesis and Application of Task-Specific Bimetal-Organic Frameworks in the Synthesis of Biological Active Spiro-Oxindoles.

The use of click chemistry as a smart and suitable method for the development of new heterogeneous catalysts is based on metal-organic frameworks as well as the production of organic compounds. The development of the click chemistry method can provide a new strategy to achieve superior properties of MOFs. Here, the two metals Co and Fe are used to create a bimetallic-organic framework. In the following, the click chemistry and postmodification method are well organized and an acidic heterogeneous porous catalyst is developed. This prepared catalyst was used as a highly efficient catalyst for the preparation of new spiro-oxindoles obtained through click chemistry with good to excellent yields (80-94%). This presented catalytic system can compete with the best reported catalytic systems. The findings showed that the presence of Co and Fe metals in the MOF, and the presence of the triazole ring on the catalyst, can increase the catalytic efficiencies. This study offers novel insights into the architecture of Metal-Organic Frameworks (MOFs), click chemistry, and biologically active compounds. Additionally, the research explores the antibacterial properties of the synthesized spiro-oxindoles and catalysts. The findings reveal significant antibacterial activities of the synthesized compounds against S. aureus, MRSA, and E. coli bacteria.

Novel Pyrano[3,2-c]quinoline-1,2,3-triazole Hybrids as Potential Anti-Diabetic Agents: In Vitro α-Glucosidase Inhibition, Kinetic, and Molecular Dynamics Simulation.

In this study, a novel series of pyrano[3,2-c]quinoline-1,2,3-triazole hybrids 8a-o were synthesized and evaluated against the α-glucosidase enzyme. All compounds showed significant in vitro inhibitory activity (IC50 values of 1.19 ± 0.05 to 20.01 ± 0.02 µM) compared to the standard drug acarbose (IC50 = 750.0 µM). Among them, 2-amino-4-(3-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitrile (compound 8k) demonstrated the best inhibitory effect toward α-glucosidase (IC50 = 1.19 ± 0.05 µM) with a competitive pattern of inhibition. Since compound 8k was synthesized as a racemic mixture, molecular docking and dynamics simulations were performed on R- and S-enantiomers of compound 8k. Based on the molecular docking results, both R- and S-enantiomers of compound 8k displayed significant interactions with key residues including catalytic triad (Asp214, Glu276, and Asp349) in the enzyme active site. However, an in silico study indicated that S- and R-enantiomers were inversely located in the enzyme active site. The R-enantiomer formed a more stable complex with a higher binding affinity to the active site of α-glucosidase than that of the S- enantiomer. The benzyl ring in the most stable complex ((R)-compound 8k) was located in the bottom of the binding site and interacted with the enzyme active site, while the pyrano[3,2-c]quinoline moiety occupied the high solvent accessible entrance of the active site. Thus, the synthesized pyrano[3,2-c]quinoline-1,2,3-triazole hybrids seem to be promising scaffolds for the development of novel α-glucosidase inhibitors.

Application of Zr-MOFs based copper complex in synthesis of pyrazolo[3, 4-b]pyridine-5-carbonitriles via anomeric-based oxidation.

In this research article, Zr-MOFs based copper complex as a novel heterogeneous and porous catalyst was designed and prepared. The structure of catalyst has verified by various techniques such as FT-IR, XRD, SEM, N2 adsorption-desorption isotherms (BET), EDS, SEM-elemental mapping, TG and DTG analysis. UiO-66-NH2/TCT/2-amino-Py@Cu(OAc)2 was used as an efficient catalyst in the synthesis of pyrazolo[3,4-b]pyridine-5-carbonitrile derivatives. The aromatization of titled molecules is performed via a cooperative vinylogous anomeric-based oxidation both under air and inert atmospheres. The unique properties of the presented method are short reaction time, high yield, reusability of catalyst, synthesis of desired product under mild and green condition.

Synthesis of Novel Pyrimido[4,5-b] Quinolines Containing Benzyloxy and 1,2,3-Triazole Moieties by DABCO as a Basic Catalyst.

DABCO was used as a basic and inexpensive catalyst for the synthesis of some new benzyloxy pyrimido[4,5-b]quinoline derivatives and 1,2,3- triazole-fused pyrimido[4,5-b]quinolines by the one-pot multi-component reaction of various benzyloxy benzaldehydes or benzylic -1,2,3-triazol-4-yl-methoxy benzaldehydes with dimedone and 6-amino-1,3-dimethyluracil at 90 °C under the solvent-free condition.

Synthesis of pyrimidine-6-carbonitriles, pyrimidin-5-ones, and tetrahydroquinoline-3-carbonitriles by new superb oxovanadium(V)-[5,10,15,20-tetrakis(pyridinium)-porphyrinato]-tetra(tricyanomethanide) catalyst via anomeric based oxidation.

Oxovanadium(V)-[5,10,15,20-tetrakis(pyridinium)-porphyrinato]-tetra(tricyanomethanide) [(VO)TPP][(TCM)4] was designed, synthesized and characterized by various techniques such as FT-IR, EDX, SEM equipped with EDX mappings, CHN elemental analysis, ICP-OES, XRD, SEM, TEM, TGA, DTA, DRS, Kubelka-Munk function (Tauc's plot), and UV-Vis analyses. Then, [(VO)TPP][(TCM)4] was used as a benign and expedient catalyst for the synthesis of numerous heterocyclic compounds such as 5-amino-7-(aryl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles, 5-amino-7-(aryl)-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles, 7-(aryl)-7,12-dihydro-5H-isochromeno[4,3-d][1,2,4]triazolo[1,5-a]pyrimidin-5-ones, and 4-(aryl)-2-(1H-indol-3-yl)-5,6,7,8-tetrahydroquinoline-3-carbonitriles under solvent-free conditions at 100 °C via a cooperative geminal-vinylogous anomeric based oxidation.

Silica sulfuric acid coated on SnFe2O4 MNPs: synthesis, characterization and catalytic applications in the synthesis of polyhydroquinolines.

An efficient and heterogeneous novel magnetic solid sulfuric acid, immobilized on silica functionalized SnFe2O4, was successfully synthesized, characterized, and employed as a novel recoverable nanocatalyst for the synthesis of biologically active polyhydroquinoline derivatives. The SnFe2O4@SiO2-SO3H was easily synthesized and confirmed using various spectroscopic techniques, including FT-IR, XRD, EDX, Map, TGA, SEM and TEM analyses. The catalytic behavior of the resulting catalyst system was investigated in the Hantzsch synthesis of polyhydroquinoline derivatives. The desired products were obtained with high conversions and excellent reusability.

Application of novel metal-organic framework [Zr-UiO-66-PDC-SO3H]FeCl4 in the synthesis of dihydrobenzo[g]pyrimido[4,5-b]quinoline derivatives.

In the current paper, we produce a new metal-organic framework (MOF) based on Zr metal, [Zr-UiO-66-PDC-SO3H]FeCl4, via an anion exchange method, which is fully characterized by FT-IR, SEM with elemental mapping and EDX, FE-SEM and TEM. Furthermore, the use of [Zr-UiO-66-PDC-SO3H]FeCl4 as a porous catalyst was examined for the one-pot synthesis of novel dihydrobenzo[g]pyrimido[4,5-b]quinoline derivatives by reaction of 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, 2-hydroxynaphthalene-1,4-dione and various aldehydes at 100 °C with good to excellent yields.

Nano-[Fe3O4@SiO2/N-propyl-1-(thiophen-2-yl)ethanimine][ZnCl2] as a nano magnetite Schiff base complex and heterogeneous catalyst for the synthesis of pyrimido[4,5-b]quinolones.

Nano-[Fe3O4@SiO2/N-propyl-1-(thiophen-2-yl)ethanimine][ZnCl2] as a nano magnetite Schiff base complex was designed and fully characterized by various analyses such as Fourier transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDX), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), differential thermal gravimetric analysis (DTA), vibrating sample magnetometry (VSM), scanning electron microscopy (SEM), and transmission electron micrographs (TEM). The presented nano magnetite Schiff base complex was used as a heterogeneous catalyst for the synthesis of pyrimido[4,5-b]quinolones by the reaction of aryl aldehyde, dimedone and 6-amino-1,3-dimethyluracil in EtOH : H2O (7 : 3) as a solvent at 60 °C.

Application of polyionic magnetic nanoparticles as a catalyst for the synthesis of carbonitriles with both indole and triazole moieties via a cooperative geminal-vinylogous anomeric-based oxidation.

Three-component reaction of aldehydes with 3-(1H-indol-3-yl)-3-oxopropanenitrile and 1H-1,2,4-triazol-5-amine under the solvent-free condition at 70 °C was effectively performed in the presence of 2 mg of polyionic magnetic nanoparticles with pyrazine bridge [Fe3O4@SiO2@(CH2)3]2-Pyrazinium-[TCM]2 as a catalyst for the synthesis of 7-aryl-5-(1H-indol-3-yl)-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles via a cooperative anomeric-based oxidation. The polyionic magnetic nanoparticles catalyst was simply recovered and reused four successive runs. The morphology and structure of MNPs catalyst were investigated by numerous techniques such as XRD, FT-IR, EDX, WDX, FE-SEM, TEM, TGA, DTA, and VSM. The obtained products are reported for the first time that were identified by various analyses techniques such as melting point, FT-IR, 1H NMR, 13C NMR, and elemental analysis (CHN). A term entitled a cooperative geminal-vinylogous anomeric-based oxidation was introduced for the latter step of the reaction mechanism for the first time. Synthesis of 7-aryl-5-(1H-indol-3-yl)-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles by using [Fe3O4@SiO2@(CH2)3]2-Pyrazinium-[TCM]2 MNPs as a catalyst.

Inhibition of Methamphetamine-Induced Cytotoxicity in the U87-Cell Line by Atorvastatin-Conjugated Carbon Nanotubes.

In biological systems, carbon nanotubes can enhance the biological effects of drugs and reduce their side effects. Methamphetamine (METH) is a stimulant drug that induces cell death in various cell types, primarily neural cells. On the other hand, specific doses of atorvastatin (ATO) can stimulate cell growth and inhibit cell death in different cell lines. This study aimed to investigate the improvement effect of ATO@single-walled carbon nanotube (SWCNT) on METH-induced cell cytotoxicity in the U87 glioblastoma cell line. In this study, cells were cultured in 10 mM of METH during the cell treatment with 0-10 nM of ATO and ATO@SWCNT. The conjugated drugs to SWCNT as Van der Waals were detected using field emission scanning electron microscopy, Fourier transform-infrared spectroscopy, and other analyses. Then, the in vitro proliferating of ATO@SWCNT was explored against glioblastoma cells compared to pure ATO. This examine was performed using methyl thiazole tetrazolium approach, terminal deoxynucleotidyl transferase deoxy uridine-triphosphate nick end labeling assay, caspase-3 method, lactate dehydrogenase assay, and RH-123 assay with 10 mM METH. The results obtained from transmission electron microscopy analysis showed the average size of 50 nm for ATO@SWCNT. This study indicated that U87 cells, which were exposed to METH and suffered cell death, were severely reduced in the presence of ATO, especially ATO@SWCNT (for its anti-apoptotic effect), but they survived. This study suggests that ATO, which was primarily used to reduce blood lipids, can significantly reduce brain cell death. The findings of this study indicate that by using SWCNT, more drugs can reach the target cells. This method reduces the total amount of required medication and shows a more beneficial therapeutic effect.

Synthesis of cobalt tetra-2,3-pyridiniumporphyrazinato with sulfonic acid tags as an efficient catalyst and its application for the synthesis of bicyclic ortho-aminocarbonitriles, cyclohexa-1,3-dienamines and 2-amino-3-cyanopyridines.

Cobalt tetra-2,3-pyridiniumporphyrazinato with sulfonic acid tag [Co(TPPASO3H)]Cl was produced and catalyzed the synthesis of ortho-aminocarbonitriles, cyclohexa-1,3-dienamines and 2-amino-3-cyanopyridines. The synthesis of 2-amino-3-cyanopyridines by using [Co(TPPASO3H)]Cl proceeded via a cooperative vinylogous anomeric based oxidation mechanism. [Co(TPPASO3H)]Cl can be recycled and reused six times with a marginal decreasing of its catalytic activity.

Targeted Development of Sustainable Green Catalysts for Oxidation of Alcohols via Tungstate-Decorated Multifunctional Amphiphilic Carbon Quantum Dots.

Achieving green and sustainable chemical processes by replacing organic solvents with water has always been one of the green chemistry goals and a challenging topic for chemists. However, the poor solubility of organic materials is a major limitation to achieving this goal, especially in alcohol oxidation. In this contribution, the development and design of amphiphilic catalysts via abundant, safe, cheaper, and more biocompatible sources have received notable attention. To this purpose, herein, our group successfully synthesized a new multifunctional amphiphilic carbon quantum dot (CQD) composed of 1-aminopropyl-3-methyl-imidazolium chloride ([APMim][Cl]), dodecylamine (DDA), and citric acid (CA) (denoted as CQDs@DDA-IL/Cl) using a one-pot hydrothermal route. The CQDs@DDA-IL/Cl was then utilized as an amphiphilic stabilizer for anchoring tungsten ions using an anion-exchange method (marked as CQDs@DDA-IL/W). The CQDs@DDA-IL/W as a reusable catalyst selectivity mediated the oxidation of alcoholic substrates with stoichiometric H2O2 in water solvent. The extraordinary performance of our catalyst was attributable to the coexistence of ionic liquid (IL) and DDA upon the surface of the CQDs@DDA-IL/W, which plays a main duty in the hydrophobic/hydrophilic balance, and significantly increase the catalyst compatibility in the aqueous medium with the purpose of removing organic solvents. As a result, the great mass transfer occurs in the two-phase medium using this amphiphilic nanocatalyst without any phase transfer catalyst (PTC) or other additives. The 100% selectivity, excellent turnover number (TON) and turnover frequency (TOF), high yield, almost complete and fast conversion of alcohol to the desired aldehydes and ketones without more oxidation, and easy and no-trouble isolation of product and catalyst are outstanding features of this catalytic system.

A comparative study on effect of metformin and metformin-conjugated nanotubes on blood glucose homeostasis in diabetic rats.

Diabetes mellitus is one of the most prevalent metabolic disorders. Carbon nanotubes have the advantage to cross the plasma membrane without damaging the cells, improving the biological effect of a drug and reducing its side effects. In the present study, the effect of metformin and metformin-conjugated nanotubes was investigated on blood glucose level in the streptozotocin-induced male diabetic rats. Diabetes in the animals was induced with a single dose of streptozotocin (60 mg/kg; i.p.) and after 3 days the blood glucose was analyzed. Animals showing fasting blood glucose higher than 250 mg/dL were considered as diabetic rats. The animals were treated with metformin and metformin-conjugated nanotubes (150 mg/kg; p.o.) daily and every 48-h for 1 week. Changes in animals' serum blood glucose level were evaluated daily during the treatment period. The results of this study showed that metformin reduced blood glucose levels in diabetic animals. Metformin-conjugated nanotubes significantly reduced the blood glucose levels in diabetic rats (p < 0.01). There was no significant difference in blood glucose level between metformin and metformin-conjugated nanotubes groups (p > 0.05). However, when both formulations of metformin were administered every 48-h, metformin-conjugated nanotubes reduced glycaemia for a longer time than metformin alone (p < 0.001). This study showed that the metformin-conjugated nanotubes would be able to reduce the blood glucose, prolong drug delivery and efficacy duration in animals which were treated with metformin-conjugated nanotubes compared with metformin alone.

Synthesis and characterization of novel polymer-drug conjugates based on the poly(styrene-alt-maleic anhydride) as a potential method for drug release.

Six well known drugs, captopril, metformin-HCl, metroniazole, nortriptyline-HCl, fluoxetine-HCl and betahistin-HCl, were grafted to poly(styrene-alt-maleic anhydride) (PSMA). Grafting was attained by combining of anhydride groups in the PSMA with therapeutic agents containing NH, OH or SH groups. The covalently grafted drugs were identified by infrared, (1)H NMR and UV-Vis spectroscopy. The drug release data at different times fits well to the Korsmeyer-Peppas equation. The analysis of the exponent n of this model revealed a dominant Fickian diffusion mechanism under the in vitro conditions. Furthermore, mean dissolution time values (45.9 to 86.7 h) indicate a high resistance against drugs transport, the highest being obtained for betahistin-HCL.

Design of ionic liquid 3-methyl-1-sulfonic acid imidazolium nitrate as reagent for the nitration of aromatic compounds by in situ generation of NO(2) in acidic media.

3-Methyl-1-sulfonic acid imidazolium nitrate ([Msim]NO(3)) as a new Brønsted acidic ionic liquid and nitrating agent was prepared and used for the efficient nitration of aromatic compounds (even aniline derivatives). The dramatic effect of this reagent by in situ generation of nitrogen dioxide as a radical on aromatic compounds to give nitroarenes has been studied.

Hantzsch reaction on free nano-Fe2O3 catalyst: excellent reactivity combined with facile catalyst recovery and recyclability.

A magnetic nanoparticle catalyst was readily prepared from inexpensive starting materials which catalyzed the Hantzsch reaction. High catalytic activity and ease of recovery from the reaction mixture using an external magnet, and several reuse times without significant losses in performance are additional eco-friendly attributes of this catalytic system.

Organic functionalization of single-walled carbon nanotubes (SWCNTs) with some chemotherapeutic agents as a potential method for drug delivery.

The grafting of drugs to the single-walled carbon nanotube (SWCNT) was attained by the initial conversion of carboxylic groups in SWCNT to corresponding acyl chlorides. The active acyl chlorides in SWCNT were subsequently mixed with chemotherapeutic agents having NH, NH2, and OH functional groups to afford the formation of relevant amide and ester, respectively. The covalently grafted drugs to SWCNT were identified by infrared and UV-visible spectroscopy and transmission electron microscopy methods. From a clinical aspect, the grafting of drugs to the SWCNT can be used as a new tool and useful method for potential drug delivery in patients.