scholarly journals Mannich Bases: An Important Pharmacophore in Present Scenario

2014 ◽  
Vol 2014 ◽  
pp. 1-15 ◽  
Author(s):  
Suman Bala ◽  
Neha Sharma ◽  
Anu Kajal ◽  
Sunil Kamboj ◽  
Vipin Saini
Keyword(s):  
Mannich Reaction ◽  
Ethacrynic Acid ◽  
Mannich Bases ◽  
Unsaturated Ketone ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Nucleophilic Addition Reaction ◽  
Antiviral Activities ◽  
Nitrogen Containing Compounds ◽  
Anti Hiv

Mannich bases are the end products of Mannich reaction and are known as beta-amino ketone carrying compounds. Mannich reaction is a carbon-carbon bond forming nucleophilic addition reaction and is a key step in synthesis of a wide variety of natural products, pharmaceuticals, and so forth. Mannich reaction is important for the construction of nitrogen containing compounds. There is a number of aminoalkyl chain bearing Mannich bases like fluoxetine, atropine, ethacrynic acid, trihexyphenidyl, and so forth with high curative value. The literature studies enlighten the fact that Mannich bases are very reactive and recognized to possess potent diverse activities like anti-inflammatory, anticancer, antifilarial, antibacterial, antifungal, anticonvulsant, anthelmintic, antitubercular, analgesic, anti-HIV, antimalarial, antipsychotic, antiviral activities and so forth. The biological activity of Mannich bases is mainly attributed to α, β-unsaturated ketone which can be generated by deamination of hydrogen atom of the amine group.

Visible-Light Photosensitized Aryl and Alkyl Decarboxylative Carbon-Heteroatom and Carbon-Carbon Bond Formations

2019 ◽  
Author(s):  
Tuhin Patra ◽  
Satobhisha Mukherjee ◽  
Jiajia Ma ◽  
Felix Strieth-Kalthoff ◽  
Frank Glorius
Keyword(s):  
Energy Transfer ◽  
Visible Light ◽  
Alkyl Radical ◽  
General Strategy ◽  
Alkyl Radicals ◽  
Bond Forming ◽  
Radical Trapping ◽  
Carbon Carbon Bond ◽  
Radical Generation ◽  
Trapping Agent

<sub>A general strategy to access both aryl and alkyl radicals by photosensitized decarboxylation of the corresponding carboxylic acids esters has been developed. An energy transfer mediated homolysis of unsymmetrical sigma-bonds for a concerted fragmentation/decarboxylation process is involved. As a result, an independent aryl/alkyl radical generation step enables a series of key C-X and C-C bond forming reactions by simply changing the radical trapping agent.</sub>

Synthesis of Novel 8-Hydroxyquinoline Derivatives through Mannich Reaction and their Biological Evaluation as Potential Immunomodulatory Agents

2020 ◽  
Vol 16 (4) ◽  
pp. 531-543
Author(s):  
Shaheen Faizi ◽  
Tahira Sarfaraz ◽  
Saima Sumbul ◽  
Almas Jabeen ◽  
Sobia A. Halim ◽  
...  
Keyword(s):  
Mannich Reaction ◽  
Aromatic Aldehydes ◽  
Mannich Bases ◽  
Biological Evaluation ◽  
Mechanism Of Inhibition ◽  
Potent Inhibition ◽  
Tnf Α ◽  
Elisa Technique ◽  
Factor Α ◽  
New Compounds

Background: In continuation of our work on Mannich reaction on 8-hydroxyquinoline, fifteen different combinations of aromatic aldehydes and aniline were subjected to Mannich reaction from which twelve products (eight Mannich bases, two imines and two intramolecularly cyclized products with benzofuranone skeleton) were obtained. Among them six compounds (1, 2, 6, 8, 9 and 12) are the new compounds. The structures of the compounds were characterized by UV, IR, MS and 1H NMR. Method: The compounds were tested for the inhibition of pro-inflammatory cytokines tumor necrosis factor-α (TNF-α) and Interleukin-1β (IL-1β) at a concentration of 25 µg/mL. The cytokines were produced by THP-1 cells differentiated with PMA for 24hrs and stimulated with LPS for 4 hrs and supernatant were analyzed through ELISA technique. Results and Discussion: Compounds 1-5, 8 and 9 inhibited the production of TNF-α and IL-1β. Compounds 1, 3, and 8 exerted potent inhibitions of TNF-α with 71%, 71%, and 83% inhibition, respectively. Compounds 1 and 8 significantly inhibited the production of IL-1β with 64% and 78% inhibition, respectively. Conclusion: Compounds 1 and 8 significantly inhibited the production of IL-1β with 64% and 78% inhibition, respectively. Notably compound 8 showed the most potent inhibition of these cytokines. Additionally, the effect of compounds on viability of THP-1 cells was also evaluated. Moreover, molecular docking was carried out to study the mechanism of inhibition of TNF-α production.

Microwave-accelerated Carbon-carbon and Carbon-heteroatom Bond Formation via Multi-component Reactions: A Brief Overview

2020 ◽  
Vol 7 (1) ◽  
pp. 23-39 ◽  
Author(s):  
Kantharaju Kamanna ◽  
Santosh Y. Khatavi
Keyword(s):  
Organic Synthesis ◽  
Bond Formation ◽  
Cycloaddition Reaction ◽  
Nanoparticle Synthesis ◽  
Single Step ◽  
Bioactive Molecules ◽  
One Pot ◽  
Bond Forming ◽  
Material Interest ◽  
Carbon Carbon Bond

Multi-Component Reactions (MCRs) have emerged as an excellent tool in organic chemistry for the synthesis of various bioactive molecules. Among these, one-pot MCRs are included, in which organic reactants react with domino in a single-step process. This has become an alternative platform for the organic chemists, because of their simple operation, less purification methods, no side product and faster reaction time. One of the important applications of the MCRs can be drawn in carbon- carbon (C-C) and carbon-heteroatom (C-X; X = N, O, S) bond formation, which is extensively used by the organic chemists to generate bioactive or useful material synthesis. Some of the key carbon- carbon bond forming reactions are Grignard, Wittig, Enolate alkylation, Aldol, Claisen condensation, Michael and more organic reactions. Alternatively, carbon-heteroatoms containing C-N, C-O, and C-S bond are also found more important and present in various heterocyclic compounds, which are of biological, pharmaceutical, and material interest. Thus, there is a clear scope for the discovery and development of cleaner reaction, faster reaction rate, atom economy and efficient one-pot synthesis for sustainable production of diverse and structurally complex organic molecules. Reactions that required hours to run completely in a conventional method can now be carried out within minutes. Thus, the application of microwave (MW) radiation in organic synthesis has become more promising considerable amount in resource-friendly and eco-friendly processes. The technique of microwaveassisted organic synthesis (MAOS) has successfully been employed in various material syntheses, such as transition metal-catalyzed cross-coupling, dipolar cycloaddition reaction, biomolecule synthesis, polymer formation, and the nanoparticle synthesis. The application of the microwave-technique in carbon-carbon and carbon-heteroatom bond formations via MCRs with major reported literature examples are discussed in this review.

Nickel-Catalyzed Electronically-Reversed Enantioselective Hydrocarbofunctionalizations of Acrylamides

Synlett ◽  
2021 ◽  
Author(s):  
Lou Shi ◽  
Wei Shu
Keyword(s):  
Nickel Catalyst ◽  
Functional Group ◽  
Optically Active ◽  
Forming Process ◽  
Carbon Bond ◽  
Bond Forming ◽  
Synthetic Strategy ◽  
Carbon Carbon Bond ◽  
Wide Range ◽  
Simple Protocol

Asymmetric hydrocarbofunctionalizations of alkenes has emerged as an efficient synthetic strategy for accessing optically active molecules via carbon-carbon bond-forming process from readily available alkenes and carbo-electrophiles. Herein, we present a summary of the efforts from our group to control the regio- and enantioselectivity of hydrocarbofunctionalizations of electron-deficient alkenes with a nickel catalyst and chiral bisoxazolidine ligand. The reaction undergoes electron-reversed hydrocarbofunctionalizations acrylamides with excellent enantioselectivity. This operationally simple protocol enables the asymmetric hydroalkylation, hydrobenzylation and hydropropargylation of acrylamides. This reaction is useful for preparing a wide range of α-branched chiral amides with broad functional group tolerance.

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