scholarly journals N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

2021 ◽  
Vol 17 ◽  
pp. 1096-1140
Author(s):  
Joseane A Mendes ◽  
Paulo R R Costa ◽  
Miguel Yus ◽  
Francisco Foubelo ◽  
Camilla D Buarque
Keyword(s):  
Nucleophilic Addition ◽  
Biological Activities ◽  
Organometallic Compounds ◽  
Research Area ◽  
Reaction Intermediates ◽  
Chiral Auxiliaries ◽  
Wide Range ◽  
Different Types ◽  
Sulfinyl Group ◽  
Enantioselective Syntheses

The synthesis of nitrogen-containing heterocycles, including natural alkaloids and other compounds presenting different types of biological activities have proved to be successful employing chiral sulfinyl imines derived from tert-butanesulfinamide. These imines are versatile chiral auxiliaries and have been extensively used as eletrophiles in a wide range of reactions. The electron-withdrawing sulfinyl group facilitates the nucleophilic addition of organometallic compounds to the iminic carbon with high diastereoisomeric excess and the free amines obtained after an easy removal of the tert-butanesulfinyl group can be transformed into enantioenriched nitrogen-containing heterocycles. The goal of this review is to the highlight enantioselective syntheses of heterocycles involving the use of chiral N-tert-butanesulfinyl imines as reaction intermediates, including the synthesis of several natural products. The synthesis of nitrogen-containing heterocycles in which the nitrogen atom is not provided by the chiral imine will not be considered in this review. The sections are organized according to the size of the heterocycles. The present work will comprehensively cover the most pertinent contributions to this research area from 2012 to 2020. We regret in advance that some contributions are excluded in order to maintain a concise format.

scholarly journals Oxazolidinones as Chiral Auxiliaries in the Asymmetric 1,4-Conjugate Addition Reaction Applied to the Total Synthesis of Natural Products: A Supplemental Mini-Review

2018 ◽  
Vol 15 (1) ◽  
pp. 3-20 ◽  
Author(s):  
Vahideh Zadsirjan ◽  
Majid M. Heravi
Keyword(s):  
Total Synthesis ◽  
Biological Activities ◽  
Conjugate Addition ◽  
Chiral Auxiliary ◽  
Addition Reactions ◽  
Chiral Auxiliaries ◽  
Complex Molecules ◽  
Total Syntheses ◽  
Naturally Occurring ◽  
Wide Range

Background: The most frequently used chiral auxiliaries, oxazolidinones (Evans' oxazolidinones) have been employed in 1,4-congugate addition reactions to α,β-unsaturated carbonyl compounds. Supplementary to our previous reports in this mini-review, we attempted to underscore the applications of this strategy in a step (steps) in the total synthesis of some naturally occurring compounds exhibiting diverse biological activities. Objective: In this mini-review, we try to underscore the applications of oxazolidinones (Evans’ oxazolidinones) in 1,4-congugate addition reactions to α,β-unsaturated carbonyl in the total synthesis of some naturally occurring compounds exhibiting diverse biological activities. Conclusion: In spite of well-known superiority of asymmetric catalyzed reactions, the use of auxiliarycontrolled reactions are still considered as commanding, vital and sometimes as only tools in the generation of stereogenic centers during the construction of complex molecules and total synthesis of naturally occurring compounds. The commercial availability, or readily accessibility of a wide variety of chiral amino alcohols as starting materials to synthesize a wide range of oxazolidinones is the merits of them. In addition, the ease of removal and subjection to various and diverse stereoselective reactions make oxazolidinones as the ideal and superior chiral auxiliaries. In this regard, they were successfully used in asymmetric 1,4-conjugate addition reactions with high stereoselectivities. The high degree of asymmetric induction can be attributed to the rigid chelation of N-acyloxazolidinones with metal ions, as well as the covering of one face of the system by the bulkiness of 4-substituent. In summary, in this report, the importance of the applications of chiral oxazolidinones as suitable chiral auxiliaries in the stereoselective, 1,4-conjugate addition reactions in asymmetric synthesis and in particular, the total synthesis of naturally occurring compounds and some complex molecules were underscored. Noticeably, in these total syntheses, this chiral auxiliary is controlling the stereochemistry of a newly created stereogenic center as well as preserving the configuration of other chiral centers, which already have been presented in the precursor. General methods have been established for the attachment of the chiral auxiliary as a moiety to the substrate molecule in high to excellent yields. At the end of these reactions, this auxiliary can be easily removed leaving various desired reactive motifs for the next step in multi-step synthesis.

scholarly journals Biochemistry, Safety, Pharmacological Activities, and Clinical Applications of Turmeric: A Mechanistic Review

2020 ◽  
Vol 2020 ◽  
pp. 1-14 ◽  
Author(s):  
Rabia Shabir Ahmad ◽  
Muhammad Bilal Hussain ◽  
Muhammad Tauseef Sultan ◽  
Muhammad Sajid Arshad ◽  
Marwa Waheed ◽  
...  
Keyword(s):  
Clinical Research ◽  
Biological Activities ◽  
Curcuma Longa ◽  
Clinical Applications ◽  
Pharmacological Activities ◽  
Neuroprotective Effects ◽  
Wide Range ◽  
Different Types ◽  
Safety And Toxicity ◽  
Anti Inflammatory

Turmeric (Curcuma longa L.) is a popular natural drug, traditionally used for the treatment of a wide range of diseases. Its root, as its most popular part used for medicinal purposes, contains different types of phytochemicals and minerals. This review summarizes what is currently known on biochemistry, safety, pharmacological activities (mechanistically), and clinical applications of turmeric. In short, curcumin is considered as the fundamental constituent in ground turmeric rhizome. Turmeric possesses several biological activities including anti-inflammatory, antioxidant, anticancer, antimutagenic, antimicrobial, antiobesity, hypolipidemic, cardioprotective, and neuroprotective effects. These reported pharmacologic activities make turmeric an important option for further clinical research. Also, there is a discussion on its safety and toxicity.

scholarly journals Synthesis of 1-(methylsulfonyl)-1-propene and N,N-dimethyl-1-propene-1-sulfonamide

2020 ◽  
Keyword(s):  
1H Nmr ◽  
Biological Activities ◽  
Coupling Constants ◽  
Base System ◽  
One Pot ◽  
Wide Range ◽  
Leaving Group ◽  
Different Types ◽  
Michael Acceptors ◽  
Vinyl Derivatives

Various vinylsulfones and vinylsulfonamides have a wide range of biological activities (mainly, inhibition of different types of enzymes) and are frequently used in synthetic organic chemistry (as active dienophiles, Michael acceptors and, generally, active agents in 1,4‑addition and electrocyclization reactions). However, despite numerous synthesized substances of this type, the synthetic protocols for the obtaining of the low molecular weight representatives of these compounds – 1‑(methylsulfonyl)-1-propene and N,N‑dimethyl-1‑propene-1-sulfonamide – seem to be still little known. In the present work we report a simple, efficient and general protocol for the dehydrative synthesis of 1‑(methylsulfonyl)-1‑propene and N,N‑dimethyl-1‑propene-1‑sulfonamide starting from corresponding 1-(methylsulfonyl)-2-propanol and N,N‑dimethyl-2‑hydroxypropanesulfonamide, respectively, using MeSO2Cl/organic base system basing on the preliminary experiment of 2‑(4‑bromophenyl)-N,N‑dimethylethenesulfonamide synthesis from 2‑(4‑bromophenyl)-2‑hydroxy-N,N-dimethylethanesulfonamide. The latter in its turn has been obtained starting from N,N‑dimethylmethanesulfonamide by lithiation with n-BuLi, subsequent action of 4‑bromobenzaldehyde and further workup. The applied protocol of vinyl derivatives synthesis allows to avoid isolation of intermediate mesyl derivatives, consisting of one-pot formation of leaving group and its elimination. Accordingly to coupling constants in 1H NMR spectra, synthesized N,N‑dimethyl-1-propene-1‑sulfonamide exists as mixture of E- and Z-isomers (in the ratio 88:12), while isolated 1‑(methylsulfonyl)-1‑propene and 2-(4-bromophenyl)-N,N‑dimethylethenesulfonamide are the most stable E‑isomers. The structures of the synthesized compounds are confirmed by the methods of 1H NMR-spectroscopy and mass-spectrometry.

Synthetic Methods and Pharmacological Potential of Different Oxazine Analogs

2021 ◽  
Vol 18 ◽  
Author(s):  
Mohammad Asif ◽  
Mohd. Imran
Keyword(s):  
Organic Chemistry ◽  
Drug Resistance ◽  
Sodium Hydroxide ◽  
Crucial Role ◽  
Heterocyclic Compounds ◽  
Biological Activities ◽  
Synthetic Methods ◽  
Wide Range ◽  
Different Types ◽  
Pharmacological Potential

: Oxazine analog is a vital class of heterocyclic compounds and has attracted synthetic interest owing to their wide range of biological activities. Oxazine analogs are valuable in medicinal organic chemistry and exhibited different varieties of biological activities such as antimicrobial, anticancer, antimalarial, antitubercular, sedative, anticonvulsant, analgesic, anti-inflammatory, antipyretic, etc. Oxazine can be derived from benzene by appropriate substitution of carbon atoms of the ring by nitrogen and oxygen atoms. Nowadays, the development of drug resistance is a key problem, and to defeat this problem, it is crucial to synthesize novel compounds. So novel oxazine analogs may play a crucial role to overcome these problems. Oxazine analogs are prepared by reaction of chalcone derivatives with thiourea in the presence of alcohol and sodium hydroxide. The present aims of this review to give an outline of some different synthetic methods and different types of biological activities of oxazine analogs. We hope that this review will be motivating for researchers concerned with oxazine analogs.

scholarly journals Synthesis, Characterization and Biological Studies of Some Organotin Compounds: (A-Review)

2020 ◽  
Vol 36 (05) ◽  
pp. 871-878
Author(s):  
Priyanka Siwacha ◽  
Surbhi Soni ◽  
Harish Kumar Sharmaa ◽  
Manoj Kumara
Keyword(s):  
Amino Acids ◽  
Biological Activities ◽  
Organometallic Compounds ◽  
Molecular Structures ◽  
Organotin Compounds ◽  
Single Source ◽  
Biological Studies ◽  
Hybrid Complex ◽  
Wide Range ◽  
Significant Attention

Significant attention has been given to organotin (IV) amino acids compounds in recent years. Organometallic compounds are better known for their potentiality to stabilize peculiar stereochemistry of their complexes and application in agriculture, catalysis and as single source precursors. Due to the better stability and diverse molecular structures the complexes own a wide range of biological activities. These individual properties create an alliance of action in the hybrid complex. In this review, we discuss the chemistry of organotin (IV) complexes and their different aspects in various fields. The aim of the present review is to evaluate the synthesis, characterization and biological activities of organotin compounds.

scholarly journals Therapeutic Potential of Glycosyl Flavonoids as Anti-Coronaviral Agents

2021 ◽  
Vol 14 (6) ◽  
pp. 546
Author(s):  
Patrícia I. C. Godinho ◽  
Raquel G. Soengas ◽  
Vera L. M. Silva
Keyword(s):  
Potential Role ◽  
Therapeutic Potential ◽  
Biological Activities ◽  
Antiviral Agent ◽  
Research Area ◽  
Therapeutic Agents ◽  
Cellular Functions ◽  
Wide Range ◽  
Low Toxicity ◽  
Socio Economic Impact

The COVID-19 pandemic, caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), has spread all over the world, creating a devastating socio-economic impact. Even though protective vaccines are starting to be administered, an effective antiviral agent for the prevention and treatment of COVID-19 is not available yet. Moreover, since new and deadly CoVs can emerge at any time with the potential of becoming pandemics, the development of therapeutic agents against potentially deadly CoVs is a research area of much current interest. In the search for anti-coronaviral drugs, researchers soon turned their heads towards glycosylated flavonoids. Glycosyl flavonoids, widespread in the plant kingdom, have received a lot of attention due to their widely recognized antioxidant, anti-inflammatory, neuroprotective, anticarcinogenic, antidiabetic, antimicrobial, and antiviral properties together with their capacity to modulate key cellular functions. The wide range of biological activities displayed by glycosyl flavonoids, along with their low toxicity, make them ideal candidates for drug development. In this review, we examine and discuss the up-to-date developments on glycosyl flavonoids as evidence-based natural sources of antivirals against coronaviruses and their potential role in the management of COVID-19.

scholarly journals A Brief Review of Phenolic Compounds Identified from Plants: Their Extraction, Analysis, and Biological Activity

2022 ◽  
Vol 17 (1) ◽  
pp. 1934578X2110697
Author(s):  
Yuanyuan Zhang ◽  
Ping Cai ◽  
Guanghui Cheng ◽  
Yongqiang Zhang
Keyword(s):  
Biological Activity ◽  
Phenolic Compounds ◽  
Secondary Metabolites ◽  
Biological Activities ◽  
Research Direction ◽  
Analysis Methods ◽  
Wide Range ◽  
Different Types ◽  
The Future ◽  
Available Information

Phenolic compounds are the most abundant secondary metabolites in plants, showing a wide range of distinct biological activities, have received more and more attention in recent years. This review aims to gather and systematize available information on the phenolic compounds from plants by discussing different types of phenolic compounds, extraction, and analysis methods, with an emphasis on their potential biological activities. The research direction and problems that should be paid attention to in the future are also put forward to provide some references for the further study of phenolic compounds.

Pharmacologically potentials of different substituted coumarin derivatives

2019 ◽  
Author(s):  
Chem Int
Keyword(s):  
Benzene Ring ◽  
Bioactive Compounds ◽  
Biological Activities ◽  
Pharmacological Properties ◽  
Coumarin Derivatives ◽  
Wide Range ◽  
Anti Oxidant ◽  
Anti Inflammatory ◽  
Coumarin Compounds

Coumarin and its derivatives are widely spread in nature. Coumarin goes to agroup as benzopyrones, which consists of a benzene ring connected to a pyronemoiety. Coumarins displayed a broad range of pharmacologically useful profile.Coumarins are considered as a promising group of bioactive compounds thatexhibited a wide range of biological activities like anti-microbial, anti-viral,antiparasitic, anti-helmintic, analgesic, anti-inflammatory, anti-diabetic, anticancer,anti-oxidant, anti-proliferative, anti-convulsant, and antihypertensiveactivities etc. The coumarin compounds have immense interest due to theirdiverse pharmacological properties. In particular, these biological activities makecoumarin compounds more attractive and testing as novel therapeuticcompounds.

Synthesis, Characterization and Antiproliferative Activity Assessment of a Novel 1H-5-mercapto-1,2,4 Triazole Derivative

2017 ◽  
Vol 68 (4) ◽  
pp. 745-747 ◽  
Author(s):  
Marius Mioc ◽  
Sorin Avram ◽  
Vasile Bercean ◽  
Mihaela Balan Porcarasu ◽  
Codruta Soica ◽  
...  
Keyword(s):  
Antiproliferative Activity ◽  
Biological Activities ◽  
Cancer Cell Line ◽  
Vascular Endothelial ◽  
Triazole Derivative ◽  
Activity Assessment ◽  
Wide Range ◽  
Specific Receptors ◽  
Endothelial Growth Factor ◽  
Selection Of

Angiogenesis plays an important function in tumor proliferation, one of the main angiogenic promoters being the vascular endothelial growth factor (VEGF) which activates specific receptors, particularly VEGFR-2. Thus, VEGFR-2 has become an essential therapeutic target in the development of new antitumor drugs. 1,2,4-triazoles show a wide range of biological activities, including antitumor effect, which was documented by numerous reports. In the current study the selection of 5-mercapto-1,2,4-triazole structure (1H-3-styryl-5-benzylidenehydrazino-carbonyl-methylsulfanil-1,2,4-triazole, Tz3a.7) was conducted based on molecular docking that emphasized it as suitable ligand for VEGFR-2 and EGFR1 receptors. Compound Tz3a.7 was synthesized and physicochemically and biologically evaluated thus revealing a moderate antiproliferative activity against breast cancer cell line MDA-MB-231.

Potential Triazole-based Molecules for the Treatment of Neglected Diseases

2019 ◽  
Vol 26 (23) ◽  
pp. 4403-4434 ◽  
Author(s):  
Susimaire Pedersoli Mantoani ◽  
Peterson de Andrade ◽  
Talita Perez Cantuaria Chierrito ◽  
Andreza Silva Figueredo ◽  
Ivone Carvalho
Keyword(s):  
Effective Treatment ◽  
Chagas Disease ◽  
Medicinal Chemistry ◽  
Biological Activities ◽  
Neglected Diseases ◽  
Triazole Derivatives ◽  
Wide Range ◽  
The World ◽  
Great Relevance ◽  
The Moment

Neglected Diseases (NDs) affect million of people, especially the poorest population around the world. Several efforts to an effective treatment have proved insufficient at the moment. In this context, triazole derivatives have shown great relevance in medicinal chemistry due to a wide range of biological activities. This review aims to describe some of the most relevant and recent research focused on 1,2,3- and 1,2,4-triazolebased molecules targeting four expressive NDs: Chagas disease, Malaria, Tuberculosis and Leishmaniasis.

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