Domino protocol for the synthesis of diversely functionalized derivatives of a novel fused pentacyclic antioxidant/anticancer fluorescent scaffold: Pyrazolo[5'',1'':2',3']pyrimido[4',5':5,6][1,4]thiazino[2,3-b]quinoxaline.

Rising to the challenge of formidable multi-step reaction needed for the synthesis of polycyclic compounds, an efficient one-pot two-step procedure for the synthesis of densely functionalized novel pyrazolo[5″,1'':2',3']pyrimido[4',5':5,6] [1,4]thiazino[2,3-b]quinoxalines from synthetically accessible starting materials 6-bromo-7-chloro-3-cyano-2-(ethylthio)-5-methylpyrazolo[1,5-a]pyrimidine, 3-aminoquinoxaline-2-thiol and some readily accessible alkyl halides was established. The domino reaction pathway involves cyclocondensation/N-alkylation sequence in K2CO3/N,N-dimethyl formamide under heating condition. DPPH free radical scavenging activity of all synthesized pyrazolo[5″,1'':2',3']pyrimido[4',5':5,6][1,4]thiazino[2,3-b]quinoxalines was evaluated to determine their antioxidant potentials. IC50 values were recorded in the range of 29-71 µM. N-benzyl substituted derivative represented the most effective antioxidant activity as well as antiproliferative activity against MCF-7 cells. Moreover, fluorescence in solution for these compounds exhibited strong red emission in the visible region (λflu. = 536-558 nm) with good to excellent quantum yields (61-95%). Due to their interesting fluorescence properties, these novel pentacyclic fluorophores can be used as fluorescent markers and probes for studies in biochemistry and pharmacology.

Electrospun Ta-MOF/PEBA Nanohybrids and Their CH4 Adsorption Application.

For the first time, biocompatible and biodegradable Ta-metal organic framework (MOF)/polyether block amide (PEBA) fibrous polymeric nanostructures were synthesized by ultrasonic and electrospinning routes in this study. The XRD peaks of products were wider, which is due to the significant effect of the ultrasonic and electrospinning methods on the final product. The adsorption/desorption behavior of the nanostructures is similar to that of the third type of isotherm series, which showed mesoporous behavior for the products. The sample has uniform morphology without any evidence of agglomeration. Since the adsorption and trapping of gaseous pollutants are very important, the application of the final Ta-MOF/PEBA fibrous polymeric nanostructures was investigated for CH4 adsorption. In order to achieve the optimal conditions of experiments and also systematic studies of the parameters, fractional factorial design was used. The results showed that by selecting temperature 40°C, time duration 35 min, and pressure 3 bar, the CH4 gas adsorption rate was near 4 mmol/g. Ultrasonic and electrospinning routes as well as immobilization of Ta-MOF in the PEBA fibrous network affect the performance of the final products for CH4 gas adsorption.

An Efficient Ultrasound-Assisted Synthesis of Cu/Zn Hybrid MOF Nanostructures With High Microbial Strain Performance.

Metal organic frameworks (MOFs) are a promising choice for antibacterial and antifungal activity due to their composition, unique architecture, and larger surface area. Herein, the ultrasonic method was used to synthesize the Cu/Zn-MOF material as an effective hybrid nanostructure with ideal properties. SEM images were used to investigate the product's morphology and particle size distribution. The XRD pattern revealed that the Cu/Zn hybrid MOF nanostructures had a smaller crystalline size distribution than pure Cu and Zn-MOF samples. Furthermore, the BET technique determined that the hybrid MOF nanostructures had a high specific surface area. TG analysis revealed that the hybrid MOF structures were more thermally stable than pure samples. The final product, with remarkable properties, was used as a new option in the field of antibacterial studies. Antibacterial activity was assessed using MIC and MBC against Gram negative and Gram positive strains, as well as antifungal activity using MIC and MFC. The antimicrobial properties of the synthesized Cu/Zn hybrid MOF nanostructures revealed that they were more effective than commercial drugs in some cases. This study's protocol could be a new strategy for introducing new hybrid nanostructures with specific applications.

Porous Cu-MOF nanostructures with anticancer properties prepared by a controllable ultrasound-assisted reverse micelle synthesis of Cu-MOF.

The ultrasonic assisted reverse micelle method (UARM) was used to synthesize Cu-MOF from Cu(NO3)2·3H2O and 2,6-pyridine dicarboxylic acid in a 1:1 molar proportion. It has been characterized using FT-IR, XRD, nitrogen adsorption analysis, SEM and TEM-EDX. The morphology of Cu-MOFs was spherical, with an average particle size distribution of less than 100 nm. Using BET analysis, the surface area of Cu-MOF was found to be 284.94 m2/g. The porous morphology of Cu-MOF was also suggested by SEM and TEM analyses. It has anticancer properties against MCF-7 breast cancer cells. Cytotoxicity testing was performed on MCF-7 breast cancer cells using the MTT cell viability assay, and cell proliferation and viability were found to be approximately 24% higher than the control.

Synthesis of novel 2-oxospiro[indoline-3,4'-[1,3]dithiine]-5'-carbonitrile derivatives by new spiro[indoline-3,4'-[1,3]dithiine]@Cu(NO3)2 supported on Fe3O4@gly@CE MNPs as efficient catalyst and evaluation of biological activity.

New spiro[indoline-3,4'-[1,3]dithiine]@Cu(NO3)2 supported on Fe3O4@gly@CE magnetic nanoparticle were synthesized and used as efficient and recyclable catalyst in the synthesis of 2-oxospiro[indoline-3,4'-[1,3]dithiine]-5'-carbonitrile derivatives. The structure of magnetic nanoparticles were confirmed using energy-dispersive X-ray spectroscopy (EDX), X-ray diffraction (XRD), scanning electron microscopy (SEM), vibrating sample magnetometer (VSM), thermogravimetric analysis (TGA), infrared spectroscopy (FT-IR) and inductively coupled plasma optical emission spectroscopy (ICP-OES). Subsequently, antibacterial and antifungal activities in terms of inhibition zone diameter, minimum inhibitory concentration, minimum bactericidal concentration and antioxidant activity against the DPPH free radical of the derivatives were investigated. The results revealed acceptable biological effects of the synthetic derivatives and a significant relationship between their structure and biological activity were observed.

Synthesis, Characterization and Antimicrobial Evaluation of Novel 6'- Amino-spiro[indeno[1,2-b]quinoxaline[1,3]dithiine]-5'-carbonitrile Derivatives.

l,3-Dithiin with two sulfurs in its structure is a six-membered, sulfur-containing heterocyclic compound. New derivatives of 6'-amino-2'-(arylidene)spiro[indeno[1,2-b]quinoxaline[1,3]dithiine]-5'-carbonitrile were prepared by the multi-component reaction of active methylene compounds, carbon disulfide, malononitrile and multi-ring compounds containing a carbonyl group in the presence of piperidine as a catalyst at room temperature with high efficiency. The antimicrobial effects including antibacterial and antifungal effects based on inhibition zone diameter (IZD), minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC) and minimum fungicidal concentration (MFC) were studied.

Green multicomponent synthesis, antimicrobial and antioxidant evaluation of novel 5-amino-isoxazole-4-carbonitriles.

BACKGROUND: Design and synthesis of new inhibitor agents to deal with pathogenic microorganisms is expanding. In this project, an efficient, environmentally friendly, economical, rapid and mild procedure was developed for the synthesis of novel functionalized isoxazole derivatives as antimicrobial potentials. METHODS: Multicomponent reaction between malononitrile (1), hydroxylamine hydrochloride (2) and different aryl or heteroaryl aldehydes 3a-i afforded novel 5-amino-isoxazole-4-carbonitriles 4a-i in good product yields and short reaction times. Deep eutectic solvent K2CO3/glycerol was used as catalytic reaction media. Structure of all molecules were characterized by different analytical tools. In vitro inhibitory activity of all derivatives was evaluated against a variety of pathogenic bacteria including both Gram-negative and Gram-positive strains as well as some fungi. In addition, their free radical scavenging activities were assessed against DPPH. RESULTS: Broad-spectrum antimicrobial activities were observed with isoxazoles 4a, b, d. In addition, antioxidant activity of isoxazole 4i was proven on DPPH. CONCLUSIONS: In this project, compounds 4a, b, d could efficiently inhibit the growth of various bacterial and fungal pathogens. Antioxidant properties of derivative 4i were also significant. These biologically active compounds are suitable candidates to synthesize new prodrugs and drugs due to the presence of different functional groups on their rings.

MgO Nanoparticle-Catalyzed Synthesis and Broad-Spectrum Antibacterial Activity of Imidazolidine- and Tetrahydropyrimidine-2-Thione Derivatives.

The biological properties of imidazolidine- and tetrahydropyrimidine-2-thione derivatives such as antiviral, antitumor, anti-inflammatory, and analgesic activities increase the demand for mild and efficient synthetic routes. In this regard, methods such as reaction of diaminoalkanes with carbon disulfide have been developed. However, this method usually suffers from relatively long reaction times, using excess reagents, vigorous reaction conditions, and emission of pernicious hydrogen sulfide gas. In this project, MgO nanoparticle was used as an efficient, non-toxic, recyclable, and economic catalyst to synthesize cyclic five- or six-membered thioureas 3a-h via reaction of 1:1 molar ratios of 1,2- or 1,3-diaminoalkanes 1a-h and carbon disulfide in ethanol at ambient temperature. More interestingly, no hydrogen sulfide emission was detected during the reaction progress. The in vitro antimicrobial properties of synthesized compounds were investigated against 14 different Gram-positive and Gram-negative pathogenic bacteria according to CLSI (Clinical and Laboratory Standards Institute) broth microdilution and disk diffusion methods. The results were compared to those of penicillin, gentamicin, and ceftriaxone, and reported as inhibition zone diameter (IZD), the minimum inhibitory concentration (MIC), and the minimum bactericidal concentration (MBC) values. The best inhibitory effects were observed with imidazolidine-2-thiones 3c and 3d. They were effective against 14 and 11 pathogens, respectively. The structure-activity relationships of the prepared heterocyclic compounds were also studied.