scholarly journals Synthesis of 4-aryl-2,6-dimethyl-3,5-bis-N-(aryl)-carbamoyl-1,4-dihydropyridines as novel skin protecting and anti-aging agents

2017 ◽  
Vol 12 (2) ◽  
pp. 25 ◽  
Author(s):  
Aamer Saeed ◽  
Danish Shahzad ◽  
Fayaz Ali Larik ◽  
Pervaiz Ali Channar ◽  
Haroon Mahfooz ◽  
...  

<p>A series of 4-aryl-2,6-dimethyl-3,5-bis-N-(aryl)-carbamoyl-1,4-dihydropyri-dines 6a-6h were prepared by using the one-pot three component synthetic method. The target compounds 6a-6h were synthesized by reacting two molar equivalents of ketone functionality and one mole of aromatic aldehydes in ammonium acetate to obtain the desired products. The structures of newly synthesized compounds were characterized by FT-IR, 1H-NMR, 13C-NMR, and elemental analysis. All the synthesized compounds were screened for their elastase inhibition and antioxidant activity. Almost all of the com-pounds 6a-h showed good to excellent activities against elastase enzyme more than the reference drug. Compounds 6d and 6b at 0.2 ± 0.0 µM and 0.2 ± 0.0 µM were found to most potent derivatives against elastase enzyme. Compound 6a exhibited prominent free radical scavenging activity. From the results of the biological activity, we infer that some derivatives can serve as lead molecules in pharmacology.</p><p><strong>Video Clip of Methodology</strong>:</p><p>3 min 13 sec   <a href="https://youtube.com/v/gPLdpGpZhR8">Full Screen</a>   <a href="https://youtube.com/watch?v=gPLdpGpZhR8">Alternate</a></p>

Author(s):  
Vijay J. Desale ◽  
Suraj N. Mali ◽  
Bapu R. Thorat ◽  
Ramesh S. Yamgar

Background: For the past several decades, we are remarking presence of the tuberculosis (TB) as the most common infectious disease leading mortality.and antimicrobial, etc. Objective: Hydrazone containing azometine group (-NHN=CH-) compounds has been reported for broad range of bioactivities such as antiplatelet, analgesic, antiinflammatory, anticonvulsant, antidepressant, antimalarial, vasodilator , antiviral and antimicrobial, etc. Method: For synthesis of our compounds (4a-4d) and (6a-6e), we have treated aromatic amines with methyl terephthalaldehydate in methanol giving us Schiff’s bases followed by reductive amination and further treatment with hydrazine hydrate to give acid hydrazides (4a-4d). These acid hydrazides were then treated with different aromatic aldehydes to yield hydrazones (6a-6d). All our synthesized compounds were subjected to FT-IR, NMR, and UV spectroscopic characterization. Results: Compounds (4a-4d) and (6a-6e) were found to have highly potent activity against Mycobacteria tuberculosis (Vaccine strain, H37 RV strains): ATCC No- 27294 (MIC:1.6-6.25 μg/mL) than standard anti-TB drugs. Our compounds exhibited good radical scavenging potentials(0-69.2%) as checked from DPPH protocol. All compounds also demonstrated good in-silico ADMET results. Conclusion: Our current study revealed promising in-vitro antituberculosis and antioxidant profiles of hydrazidehydrazone analogues.


Drug Research ◽  
2018 ◽  
Vol 68 (07) ◽  
pp. 378-386 ◽  
Author(s):  
Tanzeela Fattah ◽  
Aamer Saeed ◽  
Pervaiz Channar ◽  
Fayaz Larik ◽  
Mubashir Hassan ◽  
...  

The present article illustrated the synthesis and characterization of a novel series of (E)-4-(substituted-benzylideneamino)-2H-chromen-2-one derivatives 4a-4j in good to excellent yields. The target compounds were synthesized by refluxing 4-aminocoumarin with aromatic aldehydes in ethanol. The structural confirmation was achieved by spectroscopic techniques such as (1H, 13C-NMR and FT-IR) and elemental analysis. The synthesized compounds were evaluated for carbonic anhydrase II (CA-II) inhibition and free radical scavenging activity. All the compounds showed CA-II inhibition in the micro molar range. The compound 4c exhibited higher potential in the series with IC50=0.0928±0.00545 µM (standard Acetazolamide IC50=0.997±0.0586 µM). Pharmacological investigations showed that the synthesized compounds 4a-4j obey Lipinsk’s rule. Compound 4c elicited drug likeness and showed drug score value of 0.05. Molecular docking analysis showed that compound 4c interacts with Asn66 and Gln91 amino acid residues. Graphical Abstract.


2017 ◽  
Vol 12 (2) ◽  
pp. 20 ◽  
Author(s):  
Gökalp İşcan ◽  
Fatih Göger ◽  
Betül Demirci ◽  
Yavuz Bülent Köse

<p>In the present study, aerial parts of <em>Nepeta cilicica</em> were hydro-distilled for the essential oil. Furthermore, air-dried plant materials were extracted with methanol. According to GC-MS results, 35 compounds were characterized in the oil (totally 92%). Caryophyllene oxide, β-caryophyllene and spathulenol (28.2, 8.9 and 4.2%) were found as main components of the oil. Sixteen compounds were detected by LC/MS, most of which were caffeoylquinic acid, luteolin and apigenin derivatives, in methanolic extract of the N. cilicica. Apart from DPPH radical scavenging activity, inhibitory effects on bacterial and yeast growth of essential oil and the methanolic extract were evaluated. Twenty-four different pathogenic bacterial and <em>Candida</em> strains were tested by M7-A7 and CLSI M27-A2 protocols respectively. The crude extract showed better inhibitory effects against bacteria strains than the essential oil. Both oil and the extract demonstrated strong inhibition on <em>C. tropicalis</em> at a concentration of 47.0 µg/mL (MIC).</p><p><strong>Video Clip of Methodology</strong>:</p><p>CLSI microdilution broth method: 3 min 46 sec   <a href="https://youtube.com/v/PBADMG2zG1c">Full Screen</a>   <a href="https://youtube.com/watch?v=PBADMG2zG1c">Alternate</a></p>


2022 ◽  
Vol 16 ◽  
Author(s):  
Mustapha Dib ◽  
Marieme Kacem ◽  
Soumaya Talbi ◽  
Hajiba Ouchetto ◽  
Khadija Ouchetto ◽  
...  

Background: Pyran is an heterocyclic oxygen-containing compound that displays a wide range of therapeutic activities. Additionally, pyran is also one of the important structural subunits widely found in pharmaceuticals products. This makes it a recent focus for researchers from the industry and academic institutions. Herein, we reported an efficient and environmentally friendly one-pot strategy for the synthesis of bioactive 4H-pyran compounds via a multicomponent reaction of ethyl acetoacetate, malononitrile and substituted aromatic aldehydes in the presence of the heterogeneous spinel catalyst ( MgAl2O4 ) under mild conditions (room temperature and green solvents). The MgAl2O4 nanocatalyst was prepared from Mg/Al-LDH with a molar ratio 3 of Mg2+/Al3+ by heat treatment at 800°C. The samples were studied by a various characterization techniques such as XRD, TG-dTG, FT-IR and N2 adsorption-desorption. Good to excellent yields and facile separation of the catalyst from the reaction mixture are two of the most appealing features of this approach. Thus, bioactive molecules with pyran units may have fascinating biological properties. An efficient and green strategy for the one-pot synthesis of bioactive 4H-pyran compounds has been described. The pyrans heterocycles were produced by multicomponent reaction of ethyl acetoacetate, malononirile and substituted aromatic aldehydes in the presence of MgAl2O4 spinel nanocatalyst under mild conditions (room temperature and green solvents). MgAl2O4 nanocatalytst was prepared from Mg/Al-LDH with a molar ratio 3 of Mg2+/Al3+ by thermal treatment at 800°C. The samples were investigated by various characterization techniques such as XRD, TG-dTG, FT-IR and N2 adsorption-desorption. The following are the appealing qualities of this unique strategy including good to exceptional yields, and ease of separation of catalyst from the reaction mixture. Thus, the obtained bioactive compounds containing pyrans motif can be exhibiting interested biological activities. Methods: The substituted 4H-pyran compounds were carried out by condensation reaction of substituted aromatic aldehydes, ethyl ethyl acetoacetate and malononirile by using MgAl2O4 nanocatalyst under sustainable conditions. Objective: To develop an efficient methodology for synthesis of 4H-pyran heterocyclic molecules may have interesting applications in biology using a heterogeneous and easily synthesized catalyst. Results: This procedure outlines the synthesis of bioactive compounds in good yields and with ease of catalyst extraction from the reaction mixture under sustainable reaction conditions. Conclusion: In conclusion, it is important to reiterate that a spinel nanostucture has been successfully prepared and fully characterized using different physicochemical analysis methods. The catalytic activity of this heterogeneous catalyst was examined through the one-pot condensation of aryl benzaldehyde, malononitrile and ethyl acetoacetate. Therefore, we have developed a green method for the preparation of 4H-pyrans derivatives using MgAl2O4 as an efficient heterogeneous catalyst. The reactions were performed under green conditions, which have many benefits such as undergoing a simple procedure, good to excellent yields and easy to separate the catalyst.


2018 ◽  
Vol 21 (4) ◽  
pp. 302-311
Author(s):  
Younes Ghalandarzehi ◽  
Mehdi Shahraki ◽  
Sayyed M. Habibi-Khorassani

Aim & Scope: The synthesis of highly substituted piperidine from the one-pot reaction between aromatic aldehydes, anilines and β-ketoesters in the presence of tartaric acid as a catalyst has been investigated in both methanol and ethanol media at ambient temperature. Different conditions of temperature and solvent were employed for calculating the thermodynamic parameters and obtaining an experimental approach to the kinetics and mechanism. Experiments were carried out under different temperature and solvent conditions. Material and Methods: Products were characterized by comparison of physical data with authentic samples and spectroscopic data (IR and NMR). Rate constants are presented as an average of several kinetic runs (at least 6-10) and are reproducible within ± 3%. The overall rate of reaction is followed by monitoring the absorbance changes of the products versus time on a Varian (Model Cary Bio- 300) UV-vis spectrophotometer with a 10 mm light-path cell. Results: The best result was achieved in the presence of 0.075 g (0.1 M) of catalyst and 5 mL methanol at ambient temperature. When the reaction was carried out under solvent-free conditions, the product was obtained in a moderate yield (25%). Methanol was optimized as a desirable solvent in the synthesis of piperidine, nevertheless, ethanol in a kinetic investigation had none effect on the enhancement of the reaction rate than methanol. Based on the spectral data, the overall order of the reaction followed the second order kinetics. The results showed that the first step of the reaction mechanism is a rate determining step. Conclusion: The use of tartaric acid has many advantages such as mild reaction conditions, simple and readily available precursors and inexpensive catalyst. The proposed mechanism was confirmed by experimental results and a steady state approximation.


2020 ◽  
Vol 17 ◽  
Author(s):  
Saeid Azimi ◽  
Niloofar Mohamadighader

Abstract: A new solid catalyst was synthesized from an ionic liquid and heterogenised by changing anion reaction. The new heterogeneous acidic catalyst was characterized by SEM images, EDS analysis, AFM images, Ft-IR, HNMR, 13CNMR and Mass Spectroscopy. It was applied to synthesis of tri-arylmethanes throughout one-pot tri-component reactions among aromatic aldehydes, N,N-dimethylaniline and other carbonic nucleophiles such as anisole and indole. Hence, synthesis of convenient and inexpensive micro-heterogeneous catalyst was introduced, the efficiency of which was confirmed. Also, various useful products were synthesized throughout this simple and clean procedure.


2019 ◽  
Vol 16 (3) ◽  
pp. 249-255
Author(s):  
Momin Khan ◽  
Umar Ali ◽  
Anis Ur Rahman ◽  
Muhammad Ibrahim ◽  
Abdul Hameed ◽  
...  

Background: The role of small molecules as antioxidants to prevent the oxidation of other molecules and inhibit them from radical formation is the area of much interest to cure disease especially cancer. Moreover, the antioxidants play important role as stabilizers to prevent oxidation of fuels and lubricants. </P><P> Methods: In the present study, fifteen tetrakis-Schiff’s bases derivatives (1-15) were synthesized and screened for their antioxidant activities. Compounds 1-15 were synthesized by continuous stirring of reaction mixture of 1,4-bis (hydrazonomethyl)benzene (1 mmol) with various substituted aromatic aldehydes (2 mmol) in distilled water using acetic acid as catalyst at room temperature for 2-10 min. </P><P> Results: Our present study showed that all compounds are better ferrous ion-chelating agents except compound 1,4-bis((E)-((E)-(3,4-dimethoxybenzylidene)hydrazono)methyl)benzene (6) (IC50 = 329.26 &#177; 4.75 &#181;M) which has slightly low activity than the standard EDTA (IC50 = 318.40 &#177; 5.53 μM). In addition, DPPH radical scavenging activity of eleven compounds showed higher activity than the standard. However, remaining four compounds showed comparable radical scavenging activity to the standard DPPH (IC50 = 257.77 &#177; 4.60 &#181;M). </P><P> Conclusion: The series of fifteen Schiff’s bases (1-15) were synthesized and evaluated as antioxidants. From both assays, it has been demonstrated that most of the tetrakis-Schiff’s bases have potential to serve as leads for the development of antioxidant agents for future research.


2021 ◽  
Vol 19 (4) ◽  
pp. 329-343
Author(s):  
Yaaser Q. Almulaiky ◽  
Ammar AL-Farga

Commiphora gileadensis is commonly used in Saudi Arabia for oral hygiene. A lack of data about its biological activity encouraged us to evaluate the antioxidant and antibacterial activities of its leaf and stem extracts. Ethanol, methanol, acetone and deionized water were tested as extraction solvents. 80% methanol gave the highest extracted concentrations of phenolic and flavonoid substances. The leaf and stem extracts were respectively evaluated for their radical scavenging activity with DPPH (EC50 = 3.39, and 1.06), ABTS (EC50 = 0.690, and 0.55), and peroxide scavenging activity (EC50 = 2.43, and 1.28). GC-MS identified a wide range of compounds that may be responsible for these activities of the results observed. The highest levels of chlorophyll, carotenoids, and lycopene were found in the leaf extract while level of proanthocyanidins was found in the stem peels extract. The peroxidase and catalase activities of stem peel extract were higher than those of the leaf extract. The findings showed that the leaf and stem peel extracts of C. gileadensis exhibited significant antibacterial activity against the test organisms. The minimum inhibitory concentrations for the plant extracts were compared with the standard reference drug Augmentin but the time–kill curves for the C. gileadensis extracts showed that they were less effective than Augmentin. Moreover, the stem peel extract exhibited stronger antibacterial activity than the leaf extract. In conclusion, C. gileadensis can be an important source of natural antioxidants, used as a healthy chewing stick for teeth brushing and oral hygiene purposes.


SynOpen ◽  
2021 ◽  
Author(s):  
Mina Ghassemi ◽  
Ali Maleki

Copper ferrite (CuFe2O4) magnetic nanoparticles (MNPs) were synthesized via thermal decomposition method and applied as a reusable and green catalyst in the synthesis of functionalized 4H-pyran derivatives using malononitrile, an aromatic aldehyde and a β-ketoester in ethanol at room temperature. Then it was characterized by Fourier transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDX) analysis, scanning electron microscopy (SEM) images, thermo gravimetric and differential thermo gravimetric (TGA/DTG) analysis. The catalyst was recovered from the reaction mixture by applying an external magnet and decanting the mixture. Recycled catalyst was reused for several times without significant loss in its activity. Running the one-pot three-component reaction at room temperature, no use of eternal energy source and using a green solvent provide benign, mild, and environmentally friendly reaction conditions; as well, ease of catalyst recovering, catalyst recyclability, no use of column chromatography and good to excellent yields are extra advantages of this work.


Chemistry ◽  
2021 ◽  
Vol 3 (3) ◽  
pp. 783-799
Author(s):  
Maryam Ariannezhad ◽  
Davood Habibi ◽  
Somayyeh Heydari ◽  
Vahideh Khorramabadi

A new magnetic supported manganese-based coordination complex (Fe3O4@SiO2@CPTMS@MBOL@ Mn) was prepared in consecutive stages and characterized via various techniques (VSM, SEM, TEM, XRD, FT-IR, EDX, TG-DTA, and ICP). To evaluate its application, it was used for synthesis of divers Indazolophthalazinetriones in a simple procedure via the one-pot three-component condensation reaction of aldehydes, dimedone, and phthalhydrazide in ethanol under reflux conditions. The Mn catalyst can be recycled without any noticeable loss in catalytic activity. Additionally, the antibacterial properties of the nano-catalyst were studied against some bacterial strains.


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