Synthesis, delivery, and molecular docking of fused quinolines as inhibitor of Hepatitis A virus 3C proteinase.

It is widely accepted that Hepatitis A virus (HAV) is responsible for liver failure and even death in older people and in people with other serious health issues; so, proposing new compounds with inhibitory activity can help to treated of these disease's. In current study, a new class of quinolines is proposed with inhibitor activity of the HAV proteinase. So, in the first step, fused quinoline derivatives has been synthesized in short reaction time (12.0 min) and high efficiency yields (94%) in presence of 1-carboxymethyl-2,3-dimethylimidazolium iodide ([cmdmim]I) ionic liquid catalyst using a new method. In the following, chemical reactivity and inhibitory activity of synthesized quinolines were evaluated in density functional theory (DFT) framework and molecular docking methodologies. High global softness (0.67 eV), low HOMOSWBNNT-LUMO4a gap (4.78 eV), and more negative adsorption energy (- 87.9 kJ mol-1) in these quinolines reveal that the 4a and 4b compounds have better delivery than other quinolines using SWBNNT as suitable carrier to target cells. Molecular docking shows that the best cavity of the HAV has - 134.2 kJ mol-1 interaction energy involving bonding and non-bonding interactions. In fact, these interactions are between fused quinolines with especial geometries and sidechain flexibility amino acids residues inside the best binding site of the HAV, as hydrogen bonding, steric, and electrostatic interactions. So, these interactions imply that proposed fused quinolines have good inhibitor activity for the HAV.

Ag-Catalyzed Multicomponent Synthesis of Heterocyclic Compounds: A Review.

The investigation of the procedures for the multi-component synthesis of heterocycles has attracted the interest of organic and medicinal chemists. The use of heterogeneous catalysts, especially transition metal catalysts in organic synthesis, can provide a new, improved alternative to traditional methods in modern synthetic chemistry. The main focus is on the utilization of silver as a catalyst for the multi-component synthesis of heterocyclic compounds. The present review describes some important reported studies for the period of 2010 to 2020. Conclusion: The present review addresses some of the important reported studies on multi-component synthesis of heterocycles in the period of 2010-2020. These approaches were performed under classical and nonclassical conditions, using Ag salts, Ag NPs, Ag on the support, Ag as co-catalysts with other transition metals, ionic liquids, acidic or basic materials. Most of the reported reactions were performed under solvent-free conditions or in green solvents and the utilized catalysts were mostly recyclable. The main aim of the present review is to provide the organic chemists with the most appropriate procedures in the multi-component synthesis of desired heterocycles using silver catalysts.

Tetramethylguanidine-functionalized melamine as a multifunctional organocatalyst for the expeditious synthesis of 1,2,4-triazoloquinazolinones.

Novel nano-ordered 1,1,3,3-tetramethylguanidine-functionalized melamine (Melamine@TMG) organocatalyst was prepared and adequately identified by various techniques including FTIR, EDX, XRD and SEM spectroscopic or microscopic methods as well as TGA and DTG analytical methods. The Melamine@TMG, as an effective multifunctional organocatalyst, was found to promote smoothly the three-component synthesis of 1,2,4-triazoloquinazolinone derivatives using cyclic dimedone, 3-amino-1,2,4-triazole and different benzaldehyde derivatives in EtOH at 40 °C. This practical method afforded the desired products in high to excellent yields (86-99%) and short reaction times (10-25 min). The main advantages of this new method are the use of heterogeneous multifunctional nanocatalyst, simple work-up procedure with no need for chromatographic purification, highly selective conversion of substrates and recyclability of the catalyst, which could be used in five consecutive runs with only a small decrease in its activity.

Introduction of Succinimide as A Green and Sustainable Organo-Catalyst for the Synthesis of Arylidene Malononitrile and Tetrahydrobenzo[b] pyran Derivatives.

AIM AND OBJECTIVE: In this work, we tried to introduce a non-toxic and stable organic compound named succinimide as a green and efficient organo-catalyst for the promotion of the synthesis of arylidene malononitrile and tetrahydrobenzo[b]pyran derivatives. Using this method led to a clean procedure to achieve these types of bioactive compounds without a specific purification step. The rate and yield of the reactions were excellent, and also succinimide showed acceptable reusability as the catalyst. MATERIALS AND METHODS: In a 25 mL round-bottom flask, [A: a mixture of aromatic aldehyde (1 mmol), malononitrile (1.1 mmol) and B: a mixture of aromatic aldehyde (1.0 mmol), malononitrile (1.1 mmol)] and succinimide (0.2 mmol) in H2O/ EtOH [5 mL (1:1)] was stirred at 80 °C for an appropriate time. After completion of the reaction, which was monitored by TLC [n-hexane-EtOAc (7:3)], the mixture was cooled to room temperature, and the solid product was filtered, washed several times with cold distilled water to obtain the corresponding pure product. RESULTS: After the optimization of the conditions and amount of the catalyst, a series of aromatic aldehydes containing either-electron-donating or electron-withdrawing substituents were successfully used for both of the reactions. The reactions rates and yields under the selected conditions were excellent. The nature and electronic properties of the substituents had no obvious effect on the rate and yield of the reaction. Meanwhile, the catalyst showed acceptable reusability for these two reactions. CONCLUSION: In this work, we have introduced Succinimide as a green and safe organo-catalyst for the efficient synthesis arylidene malononitrile and tetrahydrobenzo[b]pyran derivatives. The results showed that the catalyst had excellent efficiency in green aqueous media and also the reusability of the catalyst was good.

Nanoporous Na+-Montmorillonite Perchloric Acid as an Efficient and Recyclable Catalyst for the Chemoselective Protection of Hydroxyl Groups.

Nanoporous Na+-montmorillonite perchloric acid as a novel heterogeneous reusable solid acid catalyst was easily prepared by treatment of Na+-montmorillonite as a cheap and commercially available support with perchloric acid. The catalyst was characterized using a variety of techniques including X-ray powder diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), thermogravimetric analysis (TGA), energy dispersive X-ray spectroscopy (EDX), pH analysis and determination of the Hammett acidity function. The prepared reagent showed excellent catalytic activity for the chemoselective conversion of alcohols and phenols to their corresponding trimethylsilyl ethers with 1,1,1,3,3,3-hexamethyldisilazane (HMDS) at room temperature. Deprotection of the resulting trimethylsilyl ethers can also be carried out using the same catalyst in ethanol. All reactions were performed under mild and completely heterogeneous reaction conditions in good to excellent yields. The notable advantages of this protocol are: short reaction times, high yields, availability and low cost of the reagent, easy work-up procedure and the reusability of the catalyst during a simple filtration.

A rapid one-pot synthesis of pyrido[2,3-d]pyrimidine derivatives using Brønsted-acidic ionic liquid as catalyst.

Pyrido[2,3-d]pyrimidine derivatives were synthesized regioselectivly in good to high yields by one-pot three-component condensation of 6-amino-2-(methylthio)pyrimidin-4(3H)-one, aromatic aldehydes and ethylcyanoacetate or meldrum's acid using 1,2-dimethyl-N-butanesulfonic acid imidazolium hydrogen sulfate ([DMBSI]HSO4) Brønsted-acidic ionic liquid as catalyst. Solvent-free mild reaction conditions, short reaction times, easy work-up, and reusability of the catalyst are the main advantages of this protocol.

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.

An expeditious regioselective synthesis of novel bioactive indole-substituted chromene derivatives via one-pot three-component reaction.

Novel fused 1H-benzo[f]chromen-indole derivatives were synthesized regioselectivly in good to high yields by triethyl amine catalyzed condensation of 3-cyanoacetylindoles, ß-naphthol and aryl aldehydes in methanol under ultrasounic irradiations and conventional conditions. The easy work-up of the products, rapidity, and mild reaction conditions are notable features of this protocol. The antibacterial activity of the selected products was examined. Some products showed promising activities.

An efficient one-pot synthesis of new 2-imino-1,3-thiazolidin-4-ones under ultrasonic conditions.

A convenient one-pot protocol was developed for the synthesis of 2-imino-1,3-thiazolidin-4-ones by the reaction of amines, isocyanates, aldehydes, and chloroform in the presence of sodium hydroxide under ultrasonic conditions in high yields (75-91%) and shorter reaction times (12-15 min).

A convenient ultrasound-promoted regioselective synthesis of fused polycyclic 4-aryl-3-methyl-4,7-dihydro-1H-pyrazolo[3,4-b]pyridines.

Fused polycyclic 4-aryl-3-methyl-4,7-dihydro-1H-pyrazolo[3,4-b]pyridines were obtained in a three-component regioselective reaction of 5-amino-3-methyl-1H-pyrazole, 2H-indene-1,3-dione and arylaldehydes in ethanol under ultrasound irradiation. This rapid method produced the products in short reaction times (4-5min) and excellent yields (88-97%).

An efficient one-pot three-component synthesis of fused 1,4-dihydropyridines using HY-zeolite.

A facile and convenient protocol was developed for the fast (2.5-3.5 h) and high yielding (70-90%) synthesis of fused 1,4-dihydropyridines from dimedone in the presence of HY-zeolite as an efficient recyclable heterogeneous catalyst.

An efficient ultrasound-promoted synthesis of the Baylis-Hillman adducts catalyzed by imidazole and L-proline.

A convenient protocol was developed for the synthesis of the Baylis-Hillman adducts in the presence of weak Lewis base and l-proline at room temperature under ultrasound irradiation. This method provided the products in good to high yields (65-90%) and reasonable reaction times.

KSF: an efficient catalyst for the regioselective synthesis of 1,5-diaryl pyrazoles using Baylis-Hillman adducts.

A facile and convenient protocol was developed for the regioselective synthesis of 1,5-diarylpyrazoles using Baylis-Hillman adducts over KSF catalyst in high yields (70-90%) and low reaction times.