scholarly journals Synthesis and Toxicity Evaluation of New Pyrroles Obtained by the Reaction of Activated Alkynes with 1-Methyl-3-(cyanomethyl)benzimidazolium Bromide

Molecules ◽  
2021 ◽  
Vol 26 (21) ◽  
pp. 6435
Author(s):  
Beatrice-Cristina Ivan ◽  
Florea Dumitrascu ◽  
Adriana Iuliana Anghel ◽  
Robert Viorel Ancuceanu ◽  
Sergiu Shova ◽  
...  
Keyword(s):  
Acute Toxicity ◽  
Daphnia Magna ◽  
Animal Cell ◽  
Triticum Aestivum L ◽  
Channel Blockers ◽  
One Pot ◽  
Pyrrole Derivatives ◽  
Activated Alkynes ◽  
The One ◽  
New Compounds

A series of new pyrrole derivatives were designed as chemical analogs of the 1,4-dihydropyridines drugs in order to develop future new calcium channel blockers. The new tri- and tetra-substituted N-arylpyrroles were synthesized by the one-pot reaction of 1-methyl-3-cyanomethyl benzimidazolium bromide with substituted alkynes having at least one electron-withdrawing substituent, in 1,2-epoxybutane, acting both as the solvent and reagent to generate the corresponding benzimidazolium N3-ylide. The structural characterization of the new substituted pyrroles was based on IR, NMR spectroscopy as well as on single crystal X-ray analysis. The toxicity of the new compounds was assessed on the plant cell using Triticum aestivum L. species and on the animal cell using Artemia franciscana Kellogg and Daphnia magna Straus crustaceans. The compounds showed minimal phytotoxicity on Triticum rootlets and virtually no acute toxicity on Artemia nauplii, while on Daphnia magna, it induced moderate to high toxicity, similar to nifedipine. Our research indicates that the newly synthetized pyrrole derivatives are promising molecules with biological activity and low acute toxicity.

ChemInform Abstract: A Facile Strategy for the One-Pot Multicomponent Synthesis of Spiro Dihydropyridine from Amines and Activated Alkynes.

ChemInform ◽  
2012 ◽  
Vol 43 (13) ◽  
pp. no-no
Author(s):  
Selvarangam E. Kiruthika ◽  
Neelakandan Vidhya Lakshmi ◽  
Babu Rasidha Banu ◽  
Paramasivan T. Perumal
Keyword(s):  
Multicomponent Synthesis ◽  
One Pot ◽  
Activated Alkynes ◽  
The One

Nano-cuprous oxide catalyzed one-pot synthesis of a carbazole-based STAT3 inhibitor: a facile approach via intramolecular C–N bond formation reactions

RSC Advances ◽  
2016 ◽  
Vol 6 (43) ◽  
pp. 36775-36785 ◽  
Author(s):  
C. P. Baburajeev ◽  
Chakrabhavi Dhananjaya Mohan ◽  
Govindagouda S. Patil ◽  
Shobith Rangappa ◽  
Vijay Pandey ◽  
...  
Keyword(s):  
Cuprous Oxide ◽  
Inhibitory Activity ◽  
Bond Formation ◽  
One Pot ◽  
Carbazole Derivatives ◽  
One Pot Synthesis ◽  
The One ◽  
New Compounds ◽  
Bond Formation Reactions

In this study, we report the one-pot synthesis of substituted carbazole derivatives using nano cuprous oxide as a catalyst and demonstrated the STAT3 inhibitory activity of new compounds.

Multicomponent Reaction of Aldehydes, Amines and Oxalacetate Analogues Leading to Biologically Attractive Pyrrole Derivatives

2020 ◽  
Vol 20 (10) ◽  
pp. 818-830
Author(s):  
Stella Manta ◽  
Nikolaos Kollatos ◽  
Christos Mitsos ◽  
Georgia-Anna Chatzieffraimidi ◽  
Ioannis Papanastasiou ◽  
...  
Keyword(s):  
Multicomponent Reaction ◽  
Point Of View ◽  
Primary Amines ◽  
One Pot ◽  
Pyrrole Derivatives ◽  
Anti Inflammatory ◽  
The One ◽  
Active Substances

Pyrrole is a very important pharmacophoric moiety. It has been widely incorporated into the skeleton of antitumor, anti-inflammatory, antibacterial, antioxidant and antifungal active substances. Access to this key heterocycle by diverse routes is particularly attractive in terms of chemistry, and also from the environmental point of view. The present minireview summarizes the reported methods for the preparation of highly substituted pyrrole derivatives based on the one-pot multicomponent reaction of aldehydes, primary amines, and oxalacetate analogues as well as their biology.

scholarly journals Synthesis of N-Heterocyclic Analogues of 28-O-Methyl Betulinate, and Their Antibacterial and Antifungal Properties

Molbank ◽  
10.3390/m1100 ◽  
2019 ◽  
Vol 2020 (1) ◽  
pp. M1100
Author(s):  
Elvira R. Shakurova ◽  
Lyudmila V. Parfenova
Keyword(s):  
Nmr Spectroscopy ◽  
Minimum Inhibitory Concentration ◽  
Methyl Ester ◽  
Inhibitory Concentration ◽  
2D Nmr ◽  
2D Nmr Spectroscopy ◽  
One Pot ◽  
The One ◽  
Antibacterial And Antifungal ◽  
New Compounds

The paper presents the results on the one-pot pyridine quaternization using betulinic 28-O-methyl ester (1) and Tempo+Br3− cation followed by reduction of the resulting salt (2) to 1,2,5,6-tetrahydropyridine derivative (3). The structures of new compounds are confirmed by means of 1D and 2D-NMR spectroscopy, as well as MALDI TOF/TOF spectrometry. The derivatives 2 and 3 are active against S. aureus at the minimum inhibitory concentration (MIC) of 4 μg/mL and 16 μg/mL, correspondingly.

One-pot synthesis of novel functionalized benzodiazepines via three-component or domino reactions

2018 ◽  
Vol 42 (24) ◽  
pp. 20032-20040 ◽  
Author(s):  
Yue-Wei Sun ◽  
Lan-Zhi Wang
Keyword(s):  
Domino Reactions ◽  
One Pot ◽  
Highly Efficient ◽  
One Pot Synthesis ◽  
The One ◽  
New Compounds

A simple and highly efficient protocol for the one-pot synthesis of novel benzodiazepines, which fused tricyclic or tetracyclic systems containing aryl, carboxyl, ester and acyl groups, was developed. Libraries of 40 new compounds were successfully synthesized via three-component or domino reactions by using a mild catalyst (γ-Fe2O3@SiO2/CeCl3) in good to excellent yields (82–97%).

A facile strategy for the one pot multicomponent synthesis of spiro dihydropyridines from amines and activated alkynes

2011 ◽  
Vol 52 (48) ◽  
pp. 6508-6511 ◽  
Author(s):  
Selvarangam E. Kiruthika ◽  
Neelakandan Vidhya Lakshmi ◽  
Babu Rasidha Banu ◽  
Paramasivan T. Perumal
Keyword(s):  
Multicomponent Synthesis ◽  
One Pot ◽  
Activated Alkynes ◽  
The One

A Series of Metal-Organic Frameworks for Selective CO2 Capture and Catalytic Oxidative Carboxylation of Olefins

2018 ◽  
Author(s):  
Huong T. D. Nguyen ◽  
Y B. N. Tran ◽  
Hung N. Nguyen ◽  
Tranh C. Nguyen ◽  
Felipe Gándara ◽  
...  
Keyword(s):  
Room Temperature ◽  
Gas Adsorption ◽  
New Materials ◽  
One Pot ◽  
Acid Gas ◽  
Naphthalene Diimide ◽  
Styrene Carbonate ◽  
Metal Organic ◽  
Adsorption Of Co ◽  
The One

<p>Three novel lanthanide metal˗organic frameworks (Ln-MOFs), namely MOF-590, -591, and -592 were constructed from a naphthalene diimide tetracarboxylic acid. Gas adsorption measurements of MOF-591 and -592 revealed good adsorption of CO<sub>2</sub> (low pressure, at room temperature) and moderate CO<sub>2</sub> selectivity over N<sub>2</sub> and CH<sub>4</sub>. Accordingly, breakthrough measurements were performed on a representative MOF-592, in which the separation of CO<sub>2</sub> from binary mixture containing N<sub>2</sub> and CO<sub>2</sub> was demonstrated without any loss in performance over three consecutive cycles. Moreover, MOF-590, MOF-591, and MOF-592 exhibited catalytic activity in the one-pot synthesis of styrene carbonate from styrene and CO<sub>2</sub> under mild conditions (1 atm CO<sub>2</sub>, 80 °C, and solvent-free). Among the new materials, MOF-590 revealed a remarkable efficiency with exceptional conversion (96%), selectivity (95%), and yield (91%). </p><br>

A Study on the Rearrangement of Dialkyl 1-Aryl-1-hydroxymethylphosphonates to Benzyl Phosphates

2020 ◽  
Vol 24 (4) ◽  
pp. 465-471 ◽  
Author(s):  
Zita Rádai ◽  
Réka Szabó ◽  
Áron Szigetvári ◽  
Nóra Zsuzsa Kiss ◽  
Zoltán Mucsi ◽  
...  
Keyword(s):  
Quantum Chemical ◽  
Room Temperature ◽  
Phase Transfer ◽  
One Pot ◽  
Substrate Dependence ◽  
Triethylbenzylammonium Chloride ◽  
One Step ◽  
The Pudovik Reaction ◽  
The One ◽  
Solid Liquid

The phospha-Brook rearrangement of dialkyl 1-aryl-1-hydroxymethylphosphonates (HPs) to the corresponding benzyl phosphates (BPs) has been elaborated under solid-liquid phase transfer catalytic conditions. The best procedure involved the use of triethylbenzylammonium chloride as the catalyst and Cs2CO3 as the base in acetonitrile as the solvent at room temperature. The substrate dependence of the rearrangement has been studied, and the mechanism of the transformation under discussion was explored by quantum chemical calculations. The key intermediate is an oxaphosphirane. The one-pot version starting with the Pudovik reaction has also been developed. The conditions of this tandem transformation were the same, as those for the one-step HP→BP conversion.

An Overview of the One-pot Synthesis of Imidazolines

2020 ◽  
Vol 24 (20) ◽  
pp. 2341-2355
Author(s):  
Thaipparambil Aneeja ◽  
Sankaran Radhika ◽  
Mohan Neetha ◽  
Gopinathan Anilkumar
Keyword(s):  
Asymmetric Catalysis ◽  
Organic Compounds ◽  
Ring Opening ◽  
Ecological Impact ◽  
Chiral Auxiliary ◽  
One Pot ◽  
One Pot Synthesis ◽  
The One ◽  
Synthetic Intermediate ◽  
Heterocyclic Moiety

One-pot syntheses are a simple, efficient and easy methodology, which are widely used for the synthesis of organic compounds. Imidazoline is a valuable heterocyclic moiety used as a synthetic intermediate, chiral auxiliary, chiral catalyst and a ligand for asymmetric catalysis. Imidazole is a fundamental unit of biomolecules that can be easily prepared from imidazolines. The one-pot method is an impressive approach to synthesize organic compounds as it minimizes the reaction time, separation procedures, and ecological impact. Many significant one-pot methods such as N-bromosuccinimide mediated reaction, ring-opening of tetrahydrofuran, triflic anhydrate mediated reaction, etc. were reported for imidazoline synthesis. This review describes an overview of the one-pot synthesis of imidazolines and covers literature up to 2020.

Synthesis and Kinetics of Highly Substituted Piperidines in the Presence of Tartaric Acid as a Catalyst

2018 ◽  
Vol 21 (4) ◽  
pp. 302-311
Author(s):  
Younes Ghalandarzehi ◽  
Mehdi Shahraki ◽  
Sayyed M. Habibi-Khorassani
Keyword(s):  
Ambient Temperature ◽  
Tartaric Acid ◽  
Aromatic Aldehydes ◽  
One Pot ◽  
Rate Determining Step ◽  
State Approximation ◽  
Solvent Free Conditions ◽  
Steady State Approximation ◽  
Absorbance Changes ◽  
The One

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.

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