scholarly journals One-Pot Multicomponent Synthesis of Methoxybenzo[h]quinoline-3-carbonitrile Derivatives; Anti-Chagas, X-ray, and In Silico ADME/Tox Profiling Studies

Molecules ◽  
2021 ◽  
Vol 26 (22) ◽  
pp. 6977
Author(s):  
Hegira Ramírez ◽  
Katiuska Charris ◽  
Esteban Fernandez-Moreira ◽  
Benjamín Nogueda-Torres ◽  
Mario V. Capparelli ◽  
...  
Keyword(s):  
In Silico ◽  
Ammonium Acetate ◽  
Aromatic Aldehydes ◽  
Multicomponent Synthesis ◽  
Activity Profile ◽  
One Pot ◽  
X Ray ◽  
Elemental Analyses ◽  
The One

Several methoxybenzo[h]quinoline-3-carbonitrile analogs were designed and synthesized in a repositioning approach to developing compounds with anti-prostate cancer and anti-Chagas disease properties. The compounds were synthesized through a sequential multicomponent reaction of aromatic aldehydes, malononitrile, and 1-tetralone in the presence of ammonium acetate and acetic acid (catalytic). The effect of the one-pot method on the generation of the target product has been studied. The compounds were in vitro screened against bloodstream trypomastigotes of T. cruzi (NINOA and INC-5 strains) and were most effective at showing a better activity profile than nifurtimox and benznidazole (reference drugs). A study in silico on absorption, distribution, metabolism, excretion, and toxicity (ADME/Tox) profiling to help describe the molecular properties related to the pharmacokinetic aspects in the human body of these compounds was reported. In addition, X-ray data for the compound 2-Amino-5,6-dihydro-4-(3-hydroxy-4-methoxy-phenyl)-8-methoxybenzo[h]quinoline-3-carbonitrile 6 was being reported. Spectral (IR, NMR, and elemental analyses) data on all final compounds were consistent with the proposed structures.

scholarly journals Poly(4-Vinylpyridinium)Hydrogen Sulfate Catalyzed an Efficient and Ecofriendly Protocol for the One-Pot Multicomponent Synthesis of 1,8-Acridinediones in Aqueous Medium

2013 ◽  
Vol 2013 ◽  
pp. 1-6 ◽  
Author(s):  
Janardhan Banothu ◽  
Rajitha Bavantula ◽  
Peter A. Crooks
Keyword(s):  
Aqueous Medium ◽  
Ammonium Acetate ◽  
Aromatic Aldehydes ◽  
Hydrogen Sulfate ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Multicomponent Condensation ◽  
Green Protocol ◽  
The One ◽  
Work Up

Highly efficient, ecofriendly, and improved protocol for the synthesis of 1,8-acridinediones has been developedviaone-pot multicomponent condensation of 1,3-cyclohexanedione/dimedone, aromatic aldehydes, and ammonium acetate utilizing poly(4-vinylpyridinium)hydrogen sulfate as catalyst in aqueous medium. Excellent yields in shorter reaction time, simple work-up procedure, easy recovery, and reusability of the catalyst are attractive features of this green protocol.

TiO2 Nanoparticles as an Efficient Catalyst for the One-pot Preparation of Tetrahydrobenzo[c]acridines in Aqueous Media

2013 ◽  
Vol 68 (4) ◽  
pp. 362-366 ◽  
Author(s):  
Shahrzad Abdolmohammadi ◽  
Mahdieh Mohammadnejad ◽  
Faezeh Shafaei
Keyword(s):  
Ammonium Acetate ◽  
Titanium Dioxide Nanoparticles ◽  
Aqueous Media ◽  
Aromatic Aldehydes ◽  
Catalytic Amount ◽  
One Pot ◽  
Efficient Catalyst ◽  
The One ◽  
Work Up ◽  
Operational Simplicity

A series of tetrahydrobenzo[c]acridinone derivatives have been prepared by a one-pot fourcomponent reaction of 1-naphthol, aromatic aldehydes, dimedone, and ammonium acetate in aqueous media using a catalytic amount of titanium dioxide nanoparticles (TiO2 NPs). The advantages of this novel protocol include the excellent yields, operational simplicity, short reaction time, easy work-up, reusability of the catalyst and an environmentally friendly procedure.

CeCl3·7H2O as mild and efficient catalyst for the one-pot multicomponent synthesis of 8-aryl-7,8-dihydro[1,3]dioxolo[4,5-g]chromen-6-ones

2011 ◽  
Vol 76 (4) ◽  
pp. 235-241 ◽  
Author(s):  
Li-Qiang Wu ◽  
Wei-Lin Li ◽  
Fu-Lin Yan
Keyword(s):  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
Three Component Reaction ◽  
The One ◽  
High Yields ◽  
Work Up

A series of new 8-aryl-7,8-dihydro[1,3]dioxolo[4,5-g]chromen-6-ones were synthesized via a three-component reaction of 3,4-methylenedioxyphenol, aromatic aldehydes and Meldrum’s acid in the presence of CeCl3·7H2O under solvent-free conditions. The method provided several advantages such as easy work-up, high yields and environmentally benign procedure.

Synthesis, Characterization and Biological Studies of Some Bioactive Thiazolotriazole Derivatives

2010 ◽  
Vol 65 (12) ◽  
pp. 1509-1515 ◽  
Author(s):  
Manjunatha Kumsi ◽  
Boja Poojary ◽  
Prajwal Lourdes Lobo ◽  
Nalilu Suchetha Kumari ◽  
Anoop Chullikana
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Good Yield ◽  
Sodium Acetate ◽  
Aromatic Aldehydes ◽  
Antimicrobial Activities ◽  
One Pot ◽  
Biological Studies ◽  
Elemental Analyses

The key precursor rac-2-(4-isobutylphenyl)ethyl-1,2,4-triazole-5-thione (3) was synthesized in good yield from Ibuprofen (1). One-pot three-component reactions of 3 with 5-aryl-furan-2-carboxaldehydes/ substituted aromatic aldehydes and monochloroacetic acid in acetic acid in the presence of acetic anhydride and anhydrous sodium acetate afforded substituted thiazolo[3,2-b][1,2,4]triazole derivatives 4 and 5. The structures of the newly synthesized compounds were elucidated by elemental analyses and spectral data. The compounds were tested for their in-vitro antimicrobial activities.

1-Ethyl-3-Methylimidazolium Cyanoborohydride Catalyzed Solvent Free Microwave Assisted One Pot Multicomponent Synthesis of Tetrahydroben-zo[b]Pyran Derivatives

2021 ◽  
Vol 18 ◽  
Author(s):  
Rajesh K. Manjul ◽  
Vilas B. Gade ◽  
Dhananjay N. Gaikwad ◽  
Dayanand M. Suryavanshi ◽  
Anjali S. Rajbhoj ◽  
...  
Keyword(s):  
Maximum Yield ◽  
Aromatic Aldehydes ◽  
Structural Features ◽  
Solvent Free ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Solvent Free Condition ◽  
Green Approach ◽  
13C Nuclear Magnetic Resonance ◽  
The One

: We present a facile and environmentally benign protocol for the synthesis of tetrahydrobenzo[b]pyran derivatives via multi-component condensation of dimedon, malononitrile and different aromatic aldehydes in presence of 1-ethyl-3-methylimidazolium cyanoborohydride ([EMIm][BH3CN]) as catalyst under microwave irradiation. The one-pot synthesis, facile solvent-free condition and good isolated yield illustrate the utility of this green approach. The structural features are de-rived using analytical tools including Fourier Transform Infrared Spectroscopy (FT‐IR) and 1H and 13C Nuclear Magnetic Resonance (NMR) Spectroscopy. Electronic synthesis of tetrahydrobenzo[b]pyran derivatives by using catalytic action of 1-ethyl-3-methylimidazolium cyanoborohydride has been used to obtain maximum yield.

scholarly journals Three Multi-Components Reaction: Synthesis and X-Ray Single-Crystal of Hydroacridinone-Based Hydrazino-S-Triazine Derivative as a New Class of Urease Inhibitor

Crystals ◽  
2019 ◽  
Vol 10 (1) ◽  
pp. 14 ◽  
Author(s):  
Assem Barakat ◽  
Saied M. Soliman ◽  
Ayman El-Faham ◽  
M. Ali ◽  
Abdullah Mohammed Al-Majid ◽  
...  
Keyword(s):  
Structural Features ◽  
Acetohydroxamic Acid ◽  
Orthorhombic Crystal System ◽  
Orthorhombic Crystal ◽  
One Pot ◽  
X Ray ◽  
New Class ◽  
Hirshfeld Surfaces ◽  
The One

The one-pot fashion of three multi-component reaction provides the desired hydroacridinone-based hydrazino-s-triazine scaffold 4. Compound 4 was crystallized in an orthorhombic crystal system and Pbca space group with a = 11.6271(2) Å, b = 18.2018(4) Å, c = 32.4721(6) Å, and α = β = γ = 90° with one formula unit per asymmetric unit and eight molecules per unit cell. Additionally, structural features, Hirshfeld surfaces, and DFT studies were also investigated. Its packing in the crystal is controlled by H…H (63.4%), O…H (12.7%), Cl…H (7.2%), N…H (4.7%), and C…H (10.2%) contacts, where the O…H and Cl…H contacts were found the strongest. In vitro urease inhibition evaluation showed that the hydroacridinone-based hydrazino-s-triazine is more active (IC50 = 17.9 ± 0.47 µM) than the standard acetohydroxamic acid (IC50 = 20.3 ± 0.43 µM).

scholarly journals ZnS/CuFe2O4: Magnetic Hybrid Nanocomposite to Catalyze the Synthesis of 2,4,5-triaryl-1H-imidazole Derivatives

Proceedings ◽  
2019 ◽  
Vol 41 (1) ◽  
pp. 44
Author(s):  
Fereshte Hassanzadeh-Afruzi ◽  
Shahrzad Bahrami ◽  
Ali Maleki
Keyword(s):  
Catalytic Activity ◽  
Ammonium Acetate ◽  
Aromatic Aldehydes ◽  
Cost Effective ◽  
Pharmacological Activities ◽  
One Pot ◽  
Imidazole Derivatives ◽  
The One ◽  
Co Precipitation ◽  
Appreciable Reduction

Integration of nanomaterials is an entirely new method to synthesis efficient catalysts. These compounds provided new characteristics and distinctive application which is not accessible in the single-particle nanostuctures. Although there is little catalytic activity in each component of the hybrid material, their hybrid displays much higher activity. Indeed, the presence of intermediate metal and their oxides in the framework of hybrid catalyst caused a synergistic effect, thus facilitate the organic reaction more effectively. The extensive biochemical and pharmacological activities of imidazole-containing compounds have required the development of efficient methods for synthesizing these compounds, which is a significant topic in organic chemistry. The imidazole nucleus function as a main scaffold for constructing of biologically important molecules. The ZnS/CuFe2O4 magnetic hybrid nanocatalyst was synthesized by a simple co precipitation and characterized by conventional analyses successfully. Synthesized nanocomposite was utilized as a magnetic and heterogeneous catalyst for the one-pot synthesis of 2,4,5-triaryl-1H-imidazole derivatives with condensation of various aromatic aldehydes, benzil and ammonium acetate. The presented method shows some advantages such as mild conditions, good yields, and simple separation of products from the reaction mixture and cost-effective catalyst. The experimental data showed ZnS/CuFe2O4 nanocatalyst were easily separated from the reaction mixture using an external magnetic field and use again five times in subsequent reactions without appreciable reduction in catalytic activity.

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